text:
Pex silently builds bad pexfile

This is on OSX against pex 1.4.2 using python 2.7.13.
Same command works against pex 1.3.2
Command:
$ pex -r requirements.txt -o env.pex

Contents of requirements.txt:
# === Main Dependencies
flask>=0.0
pathlib2
dulwich
pandas
codenamize
pyOpenSSL>=16.2.0
jupyter

When attempting to run env.pex:
$ ./env.pex
Failed to execute PEX file, missing macosx_10_12_x86_64-cp-27-cp27m compatible dependencies for:
ipython
appnope

Interestingly, changing the requirements.txt to include appnope and ipython==5.7 explicitly fixes it against pex 1.4.2.
As mentioned, the same works either way against pex 1.3.2.

thanks for the bug report, we'll take a look.

confirming a regression and minimal repro on OSX:
[omerta ~]$ pex pex==1.3.2 -c pex -o ./pex1.3.2.pex
[omerta ~]$ pex pex==1.4.2 -c pex -o ./pex1.4.2.pex
[omerta ~]$ ./pex1.3.2.pex jupyter
Python 2.7.13 (default, Mar  2 2017, 16:22:01)
[GCC 4.2.1 Compatible Apple LLVM 8.0.0 (clang-800.0.42.1)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>> import appnope
>>>
[omerta ~]$ ./pex1.4.2.pex jupyter
Failed to execute PEX file, missing macosx_10_13_x86_64-cp-27-cp27m compatible dependencies for:
ipython
appnope
[omerta ~]$

this relates to PEP496 environmental markers support - which appear to be correctly checked at runtime, but not considered at buildtime.

fix out here: https://github.com/pantsbuild/pex/pull/500

this should now be fixed in pex 1.4.3 - give it a shot and let me know if you hit any further issues.

Worked for me, thanks @kwlzn for a quick fix.
Still getting some weird behavior with multi-interpreter pex files, but I suspect that stuff is related to #456

@kwlzn I am using OSX 10.13 and this issue persists with pex version 1.4.3
Failed to execute PEX file, missing macosx_10_13_x86_64-cp-27-cp27m compatible dependencies for:
datadog
simplejson

@premal I don't repro on 10.13.5 - what does ~/Downloads/pex27 --version say for you?
fwiw:
[omerta ~]$ pex datadog -vvvvvvvvvvvvv
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105d9b910>
pex: R: tags for Platform(platform='macosx_10_13_x86_64', impl='cp', version='27', abi='cp27m') x PythonInterpreter('/Users/kwilson/Python/CPython-2.7.13/bin/python2.7', PythonIdentity('CPython', 2, 7, 13), {('pynd', '0.3.6'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('virtualenv', '15.1.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('pex', '1.4.3'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('tox', '2.6.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('pbr', '3.0.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('appdirs', '1.4.2'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('packaging', '16.8'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('setuptools', '33.1.1'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('pycparser', '2.17'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('wheel', '0.29.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('wsgiref', '0.1.2'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7', ('pip', '9.0.1'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('six', '1.10.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('python', '2.7.13'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/lib-dynload', ('pluggy', '0.4.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('cffi', '1.9.1'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('pyparsing', '2.1.10'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('py', '1.4.32'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages'}) -> [('cp27', 'cp27m', 'macosx_10_13_x86_64'), ('cp27', 'cp27m', 'macosx_10_13_intel'), ('cp27', 'cp27m', 'macosx_10_13_fat64'), ('cp27', 'cp27m', 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'cp27m', 'macosx_10_8_fat64'), ('cp27', 'cp27m', 'macosx_10_8_fat32'), ('cp27', 'cp27m', 'macosx_10_8_universal'), ('cp27', 'cp27m', 'macosx_10_7_x86_64'), ('cp27', 'cp27m', 'macosx_10_7_intel'), ('cp27', 'cp27m', 'macosx_10_7_fat64'), ('cp27', 'cp27m', 'macosx_10_7_fat32'), ('cp27', 'cp27m', 'macosx_10_7_universal'), ('cp27', 'cp27m', 'macosx_10_6_x86_64'), ('cp27', 'cp27m', 'macosx_10_6_intel'), ('cp27', 'cp27m', 'macosx_10_6_fat64'), ('cp27', 'cp27m', 'macosx_10_6_fat32'), ('cp27', 'cp27m', 'macosx_10_6_universal'), ('cp27', 'cp27m', 'macosx_10_5_x86_64'), ('cp27', 'cp27m', 'macosx_10_5_intel'), ('cp27', 'cp27m', 'macosx_10_5_fat64'), ('cp27', 'cp27m', 'macosx_10_5_fat32'), ('cp27', 'cp27m', 'macosx_10_5_universal'), ('cp27', 'cp27m', 'macosx_10_4_x86_64'), ('cp27', 'cp27m', 'macosx_10_4_intel'), ('cp27', 'cp27m', 'macosx_10_4_fat64'), ('cp27', 'cp27m', 'macosx_10_4_fat32'), ('cp27', 'cp27m', 'macosx_10_4_universal'), ('cp27', 'cp27m', 'macosx_10_3_fat32'), ('cp27', 'cp27m', 'macosx_10_3_universal'), ('cp27', 'cp27m', 'macosx_10_2_fat32'), ('cp27', 'cp27m', 'macosx_10_2_universal'), ('cp27', 'cp27m', 'macosx_10_1_fat32'), ('cp27', 'cp27m', 'macosx_10_1_universal'), ('cp27', 'cp27m', 'macosx_10_0_fat32'), ('cp27', 'cp27m', 'macosx_10_0_universal'), ('cp27', 'none', 'macosx_10_13_x86_64'), ('cp27', 'none', 'macosx_10_13_intel'), ('cp27', 'none', 'macosx_10_13_fat64'), ('cp27', 'none', 'macosx_10_13_fat32'), ('cp27', 'none', 'macosx_10_13_universal'), ('cp27', 'none', 'macosx_10_12_x86_64'), ('cp27', 'none', 'macosx_10_12_intel'), ('cp27', 'none', 'macosx_10_12_fat64'), ('cp27', 'none', 'macosx_10_12_fat32'), ('cp27', 'none', 'macosx_10_12_universal'), ('cp27', 'none', 'macosx_10_11_x86_64'), ('cp27', 'none', 'macosx_10_11_intel'), ('cp27', 'none', 'macosx_10_11_fat64'), ('cp27', 'none', 'macosx_10_11_fat32'), ('cp27', 'none', 'macosx_10_11_universal'), ('cp27', 'none', 'macosx_10_10_x86_64'), ('cp27', 'none', 'macosx_10_10_intel'), ('cp27', 'none', 'macosx_10_10_fat64'), ('cp27', 'none', 'macosx_10_10_fat32'), ('cp27', 'none', 'macosx_10_10_universal'), ('cp27', 'none', 'macosx_10_9_x86_64'), ('cp27', 'none', 'macosx_10_9_intel'), ('cp27', 'none', 'macosx_10_9_fat64'), ('cp27', 'none', 'macosx_10_9_fat32'), ('cp27', 'none', 'macosx_10_9_universal'), ('cp27', 'none', 'macosx_10_8_x86_64'), ('cp27', 'none', 'macosx_10_8_intel'), ('cp27', 'none', 'macosx_10_8_fat64'), ('cp27', 'none', 'macosx_10_8_fat32'), ('cp27', 'none', 'macosx_10_8_universal'), ('cp27', 'none', 'macosx_10_7_x86_64'), ('cp27', 'none', 'macosx_10_7_intel'), ('cp27', 'none', 'macosx_10_7_fat64'), ('cp27', 'none', 'macosx_10_7_fat32'), ('cp27', 'none', 'macosx_10_7_universal'), ('cp27', 'none', 'macosx_10_6_x86_64'), ('cp27', 'none', 'macosx_10_6_intel'), ('cp27', 'none', 'macosx_10_6_fat64'), ('cp27', 'none', 'macosx_10_6_fat32'), ('cp27', 'none', 'macosx_10_6_universal'), ('cp27', 'none', 'macosx_10_5_x86_64'), ('cp27', 'none', 'macosx_10_5_intel'), ('cp27', 'none', 'macosx_10_5_fat64'), ('cp27', 'none', 'macosx_10_5_fat32'), ('cp27', 'none', 'macosx_10_5_universal'), ('cp27', 'none', 'macosx_10_4_x86_64'), ('cp27', 'none', 'macosx_10_4_intel'), ('cp27', 'none', 'macosx_10_4_fat64'), ('cp27', 'none', 'macosx_10_4_fat32'), ('cp27', 'none', 'macosx_10_4_universal'), ('cp27', 'none', 'macosx_10_3_fat32'), ('cp27', 'none', 'macosx_10_3_universal'), ('cp27', 'none', 'macosx_10_2_fat32'), ('cp27', 'none', 'macosx_10_2_universal'), ('cp27', 'none', 'macosx_10_1_fat32'), ('cp27', 'none', 'macosx_10_1_universal'), ('cp27', 'none', 'macosx_10_0_fat32'), ('cp27', 'none', 'macosx_10_0_universal'), ('py2', 'none', 'macosx_10_13_x86_64'), ('py2', 'none', 'macosx_10_13_intel'), ('py2', 'none', 'macosx_10_13_fat64'), ('py2', 'none', 'macosx_10_13_fat32'), ('py2', 'none', 'macosx_10_13_universal'), ('py2', 'none', 'macosx_10_12_x86_64'), ('py2', 'none', 'macosx_10_12_intel'), ('py2', 'none', 'macosx_10_12_fat64'), ('py2', 'none', 'macosx_10_12_fat32'), ('py2', 'none', 'macosx_10_12_universal'), ('py2', 'none', 'macosx_10_11_x86_64'), ('py2', 'none', 'macosx_10_11_intel'), ('py2', 'none', 'macosx_10_11_fat64'), ('py2', 'none', 'macosx_10_11_fat32'), ('py2', 'none', 'macosx_10_11_universal'), ('py2', 'none', 'macosx_10_10_x86_64'), ('py2', 'none', 'macosx_10_10_intel'), ('py2', 'none', 'macosx_10_10_fat64'), ('py2', 'none', 'macosx_10_10_fat32'), ('py2', 'none', 'macosx_10_10_universal'), ('py2', 'none', 'macosx_10_9_x86_64'), ('py2', 'none', 'macosx_10_9_intel'), ('py2', 'none', 'macosx_10_9_fat64'), ('py2', 'none', 'macosx_10_9_fat32'), ('py2', 'none', 'macosx_10_9_universal'), ('py2', 'none', 'macosx_10_8_x86_64'), ('py2', 'none', 'macosx_10_8_intel'), ('py2', 'none', 'macosx_10_8_fat64'), ('py2', 'none', 'macosx_10_8_fat32'), ('py2', 'none', 'macosx_10_8_universal'), ('py2', 'none', 'macosx_10_7_x86_64'), ('py2', 'none', 'macosx_10_7_intel'), ('py2', 'none', 'macosx_10_7_fat64'), ('py2', 'none', 'macosx_10_7_fat32'), ('py2', 'none', 'macosx_10_7_universal'), ('py2', 'none', 'macosx_10_6_x86_64'), ('py2', 'none', 'macosx_10_6_intel'), ('py2', 'none', 'macosx_10_6_fat64'), ('py2', 'none', 'macosx_10_6_fat32'), ('py2', 'none', 'macosx_10_6_universal'), ('py2', 'none', 'macosx_10_5_x86_64'), ('py2', 'none', 'macosx_10_5_intel'), ('py2', 'none', 'macosx_10_5_fat64'), ('py2', 'none', 'macosx_10_5_fat32'), ('py2', 'none', 'macosx_10_5_universal'), ('py2', 'none', 'macosx_10_4_x86_64'), ('py2', 'none', 'macosx_10_4_intel'), ('py2', 'none', 'macosx_10_4_fat64'), ('py2', 'none', 'macosx_10_4_fat32'), ('py2', 'none', 'macosx_10_4_universal'), ('py2', 'none', 'macosx_10_3_fat32'), ('py2', 'none', 'macosx_10_3_universal'), ('py2', 'none', 'macosx_10_2_fat32'), ('py2', 'none', 'macosx_10_2_universal'), ('py2', 'none', 'macosx_10_1_fat32'), ('py2', 'none', 'macosx_10_1_universal'), ('py2', 'none', 'macosx_10_0_fat32'), ('py2', 'none', 'macosx_10_0_universal'), ('cp27', 'none', 'any'), ('cp2', 'none', 'any'), ('py27', 'none', 'any'), ('py2', 'none', 'any')]
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105d9bad0>
pex: crawling link i=0 link=Link('file:///Users/kwilson/.pex/build') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/datadog/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/36/29/4c3340db9f5d0ff27e3ce7af621cff4f9pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/datadog-0.20.0.tar.gz                         pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/datadog-0.20.0.tar.gz :: Fetching file:///Userpex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpYxGfNZ/datadog-0pex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpYxGfNZ/datadog-0pex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpYxGfNZ/datadog-0pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105de57d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/requests/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105de57d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105de57d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/decorator/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/49/df/50aa1999ab9bde74656c2919d9c0c085fpex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/requests-2.18.4-py2.py3-none-any.whl          pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/requests-2.18.4-py2.py3-none-any.whl :: Fetchipex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpTltVsU/requests-pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/bc/bb/a24838832ba35baf52f32ab1a49b906b5pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/decorator-4.3.0-py2.py3-none-any.whl          pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/decorator-4.3.0-py2.py3-none-any.whl :: Fetchipex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmp2WfRDa/decoratorpex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_pex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpCK4sRP/simplejsopex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x1070e3390>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/certifi/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x1070e3390>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/chardet/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x1071128d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/idna/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x1071128d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/urllib3/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/63/cb/6965947c13a94236f6d4b8223e21beb4dpex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/urllib3-1.22-py2.py3-none-any.whl             pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/urllib3-1.22-py2.py3-none-any.whl :: Fetching pex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpLrt3Cp/urllib3-1pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/bc/a9/01ffebfb562e4274b6487b4bb1ddec7capex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/chardet-3.0.4-py2.py3-none-any.whl            pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/chardet-3.0.4-py2.py3-none-any.whl :: Fetchingpex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmponwBbW/chardet-3pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/7c/e6/92ad559b7192d846975fc916b65f667c7b8c3a32bea7372340bfe9a15fa5/certifi-2018.4.16-py2.py3-none-any.whl#sha256=9fa520c1bacfb634fa7af20a76bcbd3d5fb390481724c597da32c719a7dca4pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl                                                                                pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl :: Fetcpex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpRdR1oN/certifi-2pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/27/cc/6dd9a3869f15c2edfab863b9928382772pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/idna-2.6-py2.py3-none-any.whl                 pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/idna-2.6-py2.py3-none-any.whl :: Fetching filepex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmp5x4s48/idna-2.6-  datadog 0.20.0.whl into distribution
  simplejson 3.15.0
  urllib3 1.22
  chardet 3.0.4
  requests 2.18.4
  certifi 2018.4.16
  idna 2.6
  decorator 4.3.0
pex: Building pex: 4137.5ms
pex:   Resolving interpreters: 1.2ms
pex:     Setting up interpreter /Users/kwilson/Python/CPython-2.7.13/bin/python2.7: 1.2ms
pex:   Resolving distributions: 4126.9ms
pex:     Fetching https://files.pythonhosted.org/packages/36/29/4c3340db9f5d0ff27e3ce7af621cff4f9b8b45dc3191a445037972fb4757/datadog-0.20.0.tar.gz#sha256=7bb4af836d7422a6138f983b81c16acd56c2d608913982602856cc273ae74768: 143.6ms
pex:     Fetching file:///Users/kwilson/.pex/build/datadog-0.20.0.tar.gz: 6.9ms
pex:       Fetching file:///Users/kwilson/.pex/build/datadog-0.20.0.tar.gz: 6.3ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpYxGfNZ/datadog-0.20.0.tar.gz into distribution: 520.1ms
pex:       Packaging datadog: 471.7ms
pex:         Installing /var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpUCgkBz: 469.1ms
pex:     Fetching https://files.pythonhosted.org/packages/49/df/50aa1999ab9bde74656c2919d9c0c085fd2b3775fd3eca826012bef76d8c/requests-2.18.4-py2.py3-none-any.whl#sha256=6a1b267aa90cac58ac3a765d067950e7dbbf75b1da07e895d1f594193a40a38b: 125.2ms
pex:     Fetching file:///Users/kwilson/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 6.6ms
pex:       Fetching file:///Users/kwilson/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 5.7ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpTltVsU/requests-2.18.4-py2.py3-none-any.whl into distribution: 4.4ms
pex:     Fetching https://files.pythonhosted.org/packages/bc/bb/a24838832ba35baf52f32ab1a49b906b5f82fb7c76b2f6a7e35e140bac30/decorator-4.3.0-py2.py3-none-any.whl#sha256=2c51dff8ef3c447388fe5e4453d24a2bf128d3a4c32af3fabef1f01c6851ab82: 82.8ms
pex:     Fetching file:///Users/kwilson/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 7.0ms
pex:       Fetching file:///Users/kwilson/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 6.1ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmp2WfRDa/decorator-4.3.0-py2.py3-none-any.whl into distribution: 1.6ms
pex:     Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 1.2ms
pex:       Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 0.6ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpCK4sRP/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution: 1.3ms
pex:     Fetching https://files.pythonhosted.org/packages/63/cb/6965947c13a94236f6d4b8223e21beb4d576dc72e8130bd7880f600839b8/urllib3-1.22-py2.py3-none-any.whl#sha256=06330f386d6e4b195fbfc736b297f58c5a892e4440e54d294d7004e3a9bbea1b: 148.8ms
pex:     Fetching file:///Users/kwilson/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 6.7ms
pex:       Fetching file:///Users/kwilson/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 5.7ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpLrt3Cp/urllib3-1.22-py2.py3-none-any.whl into distribution: 3.4ms
pex:     Fetching https://files.pythonhosted.org/packages/bc/a9/01ffebfb562e4274b6487b4bb1ddec7ca55ec7510b22e4c51f14098443b8/chardet-3.0.4-py2.py3-none-any.whl#sha256=fc323ffcaeaed0e0a02bf4d117757b98aed530d9ed4531e3e15460124c106691: 141.4ms
pex:     Fetching file:///Users/kwilson/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 1.4ms
pex:       Fetching file:///Users/kwilson/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 0.7ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmponwBbW/chardet-3.0.4-py2.py3-none-any.whl into distribution: 1.7ms
pex:     Fetching https://files.pythonhosted.org/packages/7c/e6/92ad559b7192d846975fc916b65f667c7b8c3a32bea7372340bfe9a15fa5/certifi-2018.4.16-py2.py3-none-any.whl#sha256=9fa520c1bacfb634fa7af20a76bcbd3d5fb390481724c597da32c719a7dca4b0: 146.8ms
pex:     Fetching file:///Users/kwilson/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 6.5ms
pex:       Fetching file:///Users/kwilson/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 5.6ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpRdR1oN/certifi-2018.4.16-py2.py3-none-any.whl into distribution: 1.3ms
pex:     Fetching https://files.pythonhosted.org/packages/27/cc/6dd9a3869f15c2edfab863b992838277279ce92663d334df9ecf5106f5c6/idna-2.6-py2.py3-none-any.whl#sha256=8c7309c718f94b3a625cb648ace320157ad16ff131ae0af362c9f21b80ef6ec4: 121.1ms
pex:     Fetching file:///Users/kwilson/.pex/build/idna-2.6-py2.py3-none-any.whl: 6.1ms
pex:       Fetching file:///Users/kwilson/.pex/build/idna-2.6-py2.py3-none-any.whl: 5.2ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmp5x4s48/idna-2.6-py2.py3-none-any.whl into distribution: 1.8ms
Running PEX file at /var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmp7fRbhw with args []
pex: PEX.run invoking /Users/kwilson/Python/CPython-2.7.13/bin/python2.7 /var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmp7fRbhw
Python 2.7.13 (default, Mar  2 2017, 16:22:01)
[GCC 4.2.1 Compatible Apple LLVM 8.0.0 (clang-800.0.42.1)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>> import datadog; datadog.__file__
'/private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmp7fRbhw/.deps/datadog-0.20.0-py2-none-any.whl/datadog/__init__.py'
>>>

[omerta ~]$ pex --version
pex 1.4.3
[omerta ~]$ uname -a
Darwin omerta 17.6.0 Darwin Kernel Version 17.6.0: Tue May  8 15:22:16 PDT 2018; root:xnu-4570.61.1~1/RELEASE_X86_64 x86_64
[omerta ~]$ pex simplejson -vvvvvvvvv
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x104c9b910>
pex: R: tags for Platform(platform='macosx_10_13_x86_64', impl='cp', version='27', abi='cp27m') x PythonInterpreter('/Users/kwilson/Python/CPython-2.7.13/bin/python2.7', PythonIdentity('CPython', 2, 7, 13), {('pynd', '0.3.6'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('virtualenv', '15.1.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('pex', '1.4.3'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('tox', '2.6.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('pbr', '3.0.0'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('appdirs', '1.4.2'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('packaging', '16.8'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('setuptools', '33.1.1'): '/Users/kwilson/Python/CPython-2.7.13/lib/python2.7/site-packages', ('pycparser', '2.17'): 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'none', 'macosx_10_5_fat64'), ('cp27', 'none', 'macosx_10_5_fat32'), ('cp27', 'none', 'macosx_10_5_universal'), ('cp27', 'none', 'macosx_10_4_x86_64'), ('cp27', 'none', 'macosx_10_4_intel'), ('cp27', 'none', 'macosx_10_4_fat64'), ('cp27', 'none', 'macosx_10_4_fat32'), ('cp27', 'none', 'macosx_10_4_universal'), ('cp27', 'none', 'macosx_10_3_fat32'), ('cp27', 'none', 'macosx_10_3_universal'), ('cp27', 'none', 'macosx_10_2_fat32'), ('cp27', 'none', 'macosx_10_2_universal'), ('cp27', 'none', 'macosx_10_1_fat32'), ('cp27', 'none', 'macosx_10_1_universal'), ('cp27', 'none', 'macosx_10_0_fat32'), ('cp27', 'none', 'macosx_10_0_universal'), ('py2', 'none', 'macosx_10_13_x86_64'), ('py2', 'none', 'macosx_10_13_intel'), ('py2', 'none', 'macosx_10_13_fat64'), ('py2', 'none', 'macosx_10_13_fat32'), ('py2', 'none', 'macosx_10_13_universal'), ('py2', 'none', 'macosx_10_12_x86_64'), ('py2', 'none', 'macosx_10_12_intel'), ('py2', 'none', 'macosx_10_12_fat64'), ('py2', 'none', 'macosx_10_12_fat32'), ('py2', 'none', 'macosx_10_12_universal'), ('py2', 'none', 'macosx_10_11_x86_64'), ('py2', 'none', 'macosx_10_11_intel'), ('py2', 'none', 'macosx_10_11_fat64'), ('py2', 'none', 'macosx_10_11_fat32'), ('py2', 'none', 'macosx_10_11_universal'), ('py2', 'none', 'macosx_10_10_x86_64'), ('py2', 'none', 'macosx_10_10_intel'), ('py2', 'none', 'macosx_10_10_fat64'), ('py2', 'none', 'macosx_10_10_fat32'), ('py2', 'none', 'macosx_10_10_universal'), ('py2', 'none', 'macosx_10_9_x86_64'), ('py2', 'none', 'macosx_10_9_intel'), ('py2', 'none', 'macosx_10_9_fat64'), ('py2', 'none', 'macosx_10_9_fat32'), ('py2', 'none', 'macosx_10_9_universal'), ('py2', 'none', 'macosx_10_8_x86_64'), ('py2', 'none', 'macosx_10_8_intel'), ('py2', 'none', 'macosx_10_8_fat64'), ('py2', 'none', 'macosx_10_8_fat32'), ('py2', 'none', 'macosx_10_8_universal'), ('py2', 'none', 'macosx_10_7_x86_64'), ('py2', 'none', 'macosx_10_7_intel'), ('py2', 'none', 'macosx_10_7_fat64'), ('py2', 'none', 'macosx_10_7_fat32'), ('py2', 'none', 'macosx_10_7_universal'), ('py2', 'none', 'macosx_10_6_x86_64'), ('py2', 'none', 'macosx_10_6_intel'), ('py2', 'none', 'macosx_10_6_fat64'), ('py2', 'none', 'macosx_10_6_fat32'), ('py2', 'none', 'macosx_10_6_universal'), ('py2', 'none', 'macosx_10_5_x86_64'), ('py2', 'none', 'macosx_10_5_intel'), ('py2', 'none', 'macosx_10_5_fat64'), ('py2', 'none', 'macosx_10_5_fat32'), ('py2', 'none', 'macosx_10_5_universal'), ('py2', 'none', 'macosx_10_4_x86_64'), ('py2', 'none', 'macosx_10_4_intel'), ('py2', 'none', 'macosx_10_4_fat64'), ('py2', 'none', 'macosx_10_4_fat32'), ('py2', 'none', 'macosx_10_4_universal'), ('py2', 'none', 'macosx_10_3_fat32'), ('py2', 'none', 'macosx_10_3_universal'), ('py2', 'none', 'macosx_10_2_fat32'), ('py2', 'none', 'macosx_10_2_universal'), ('py2', 'none', 'macosx_10_1_fat32'), ('py2', 'none', 'macosx_10_1_universal'), ('py2', 'none', 'macosx_10_0_fat32'), ('py2', 'none', 'macosx_10_0_universal'), ('cp27', 'none', 'any'), ('cp2', 'none', 'any'), ('py27', 'none', 'any'), ('py2', 'none', 'any')]
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x104c9bad0>
pex: crawling link i=0 link=Link('file:///Users/kwilson/.pex/build') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_pex: Building pex :: Resolving distributions :: Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_pex: Building pex :: Resolving distributions :: Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmph5oRdR/simplejso  simplejson 3.15.0-macosx_10_12_x86_64.whl into distribution
pex: Building pex: 430.6ms
pex:   Resolving interpreters: 1.2ms
pex:     Setting up interpreter /Users/kwilson/Python/CPython-2.7.13/bin/python2.7: 1.2ms
pex:   Resolving distributions: 419.9ms
pex:     Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 5.4ms
pex:       Fetching file:///Users/kwilson/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 4.8ms
pex:     Translating /private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmph5oRdR/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution: 1.3ms
Running PEX file at /var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpbcj8Qt with args []
pex: PEX.run invoking /Users/kwilson/Python/CPython-2.7.13/bin/python2.7 /var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpbcj8Qt
Python 2.7.13 (default, Mar  2 2017, 16:22:01)
[GCC 4.2.1 Compatible Apple LLVM 8.0.0 (clang-800.0.42.1)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>> import simplejson
>>> simplejson.__file__
'/private/var/folders/kd/k5b__qgs0gl5yzp48gctmhz80000gn/T/tmpbcj8Qt/.deps/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl/simplejson/__init__.py'
>>>

@kwlzn I am running 10.13.5 on two separate boxes, both using pex 1.4.3. I can repro @premal's error on one, while it works on the other. Here is my failure:
(venv) neutronbot$ pex --version
pex 1.4.3
(venv) neutronbot$ uname -a
Darwin neutronbot 17.6.0 Darwin Kernel Version 17.6.0: Tue May  8 15:22:16 PDT 2018; root:xnu-4570.61.1~1/RELEASE_X86_64 x86_64
(venv)  neutronbot$ pex datadog -vvvvvvvvvvvv
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10ffba610>
pex: R: tags for Platform(platform='macosx_10_13_x86_64', impl='cp', version='27', abi='cp27m') x PythonInterpreter('/Users/neutronbot/sandbox/venv/bin/python', PythonIdentity('CPython', 2, 7, 10), {('python', '2.7.10'): '/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/lib-dynload', ('pip', '10.0.1'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('ipython-genutils', '0.2.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('enum34', '1.1.6'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('ptyprocess', '0.5.2'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('decorator', '4.3.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('backports.shutil-get-terminal-size', '1.0.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('six', '1.11.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('setuptools', '33.1.1'): 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'macosx_10_2_universal'), ('cp27', 'cp27m', 'macosx_10_1_fat32'), ('cp27', 'cp27m', 'macosx_10_1_universal'), ('cp27', 'cp27m', 'macosx_10_0_fat32'), ('cp27', 'cp27m', 'macosx_10_0_universal'), ('cp27', 'none', 'macosx_10_13_x86_64'), ('cp27', 'none', 'macosx_10_13_intel'), ('cp27', 'none', 'macosx_10_13_fat64'), ('cp27', 'none', 'macosx_10_13_fat32'), ('cp27', 'none', 'macosx_10_13_universal'), ('cp27', 'none', 'macosx_10_12_x86_64'), ('cp27', 'none', 'macosx_10_12_intel'), ('cp27', 'none', 'macosx_10_12_fat64'), ('cp27', 'none', 'macosx_10_12_fat32'), ('cp27', 'none', 'macosx_10_12_universal'), ('cp27', 'none', 'macosx_10_11_x86_64'), ('cp27', 'none', 'macosx_10_11_intel'), ('cp27', 'none', 'macosx_10_11_fat64'), ('cp27', 'none', 'macosx_10_11_fat32'), ('cp27', 'none', 'macosx_10_11_universal'), ('cp27', 'none', 'macosx_10_10_x86_64'), ('cp27', 'none', 'macosx_10_10_intel'), ('cp27', 'none', 'macosx_10_10_fat64'), ('cp27', 'none', 'macosx_10_10_fat32'), ('cp27', 'none', 'macosx_10_10_universal'), ('cp27', 'none', 'macosx_10_9_x86_64'), ('cp27', 'none', 'macosx_10_9_intel'), ('cp27', 'none', 'macosx_10_9_fat64'), ('cp27', 'none', 'macosx_10_9_fat32'), ('cp27', 'none', 'macosx_10_9_universal'), ('cp27', 'none', 'macosx_10_8_x86_64'), ('cp27', 'none', 'macosx_10_8_intel'), ('cp27', 'none', 'macosx_10_8_fat64'), ('cp27', 'none', 'macosx_10_8_fat32'), ('cp27', 'none', 'macosx_10_8_universal'), ('cp27', 'none', 'macosx_10_7_x86_64'), ('cp27', 'none', 'macosx_10_7_intel'), ('cp27', 'none', 'macosx_10_7_fat64'), ('cp27', 'none', 'macosx_10_7_fat32'), ('cp27', 'none', 'macosx_10_7_universal'), ('cp27', 'none', 'macosx_10_6_x86_64'), ('cp27', 'none', 'macosx_10_6_intel'), ('cp27', 'none', 'macosx_10_6_fat64'), ('cp27', 'none', 'macosx_10_6_fat32'), ('cp27', 'none', 'macosx_10_6_universal'), ('cp27', 'none', 'macosx_10_5_x86_64'), ('cp27', 'none', 'macosx_10_5_intel'), ('cp27', 'none', 'macosx_10_5_fat64'), ('cp27', 'none', 'macosx_10_5_fat32'), ('cp27', 'none', 'macosx_10_5_universal'), ('cp27', 'none', 'macosx_10_4_x86_64'), ('cp27', 'none', 'macosx_10_4_intel'), ('cp27', 'none', 'macosx_10_4_fat64'), ('cp27', 'none', 'macosx_10_4_fat32'), ('cp27', 'none', 'macosx_10_4_universal'), ('cp27', 'none', 'macosx_10_3_fat32'), ('cp27', 'none', 'macosx_10_3_universal'), ('cp27', 'none', 'macosx_10_2_fat32'), ('cp27', 'none', 'macosx_10_2_universal'), ('cp27', 'none', 'macosx_10_1_fat32'), ('cp27', 'none', 'macosx_10_1_universal'), ('cp27', 'none', 'macosx_10_0_fat32'), ('cp27', 'none', 'macosx_10_0_universal'), ('py2', 'none', 'macosx_10_13_x86_64'), ('py2', 'none', 'macosx_10_13_intel'), ('py2', 'none', 'macosx_10_13_fat64'), ('py2', 'none', 'macosx_10_13_fat32'), ('py2', 'none', 'macosx_10_13_universal'), ('py2', 'none', 'macosx_10_12_x86_64'), ('py2', 'none', 'macosx_10_12_intel'), ('py2', 'none', 'macosx_10_12_fat64'), ('py2', 'none', 'macosx_10_12_fat32'), ('py2', 'none', 'macosx_10_12_universal'), ('py2', 'none', 'macosx_10_11_x86_64'), ('py2', 'none', 'macosx_10_11_intel'), ('py2', 'none', 'macosx_10_11_fat64'), ('py2', 'none', 'macosx_10_11_fat32'), ('py2', 'none', 'macosx_10_11_universal'), ('py2', 'none', 'macosx_10_10_x86_64'), ('py2', 'none', 'macosx_10_10_intel'), ('py2', 'none', 'macosx_10_10_fat64'), ('py2', 'none', 'macosx_10_10_fat32'), ('py2', 'none', 'macosx_10_10_universal'), ('py2', 'none', 'macosx_10_9_x86_64'), ('py2', 'none', 'macosx_10_9_intel'), ('py2', 'none', 'macosx_10_9_fat64'), ('py2', 'none', 'macosx_10_9_fat32'), ('py2', 'none', 'macosx_10_9_universal'), ('py2', 'none', 'macosx_10_8_x86_64'), ('py2', 'none', 'macosx_10_8_intel'), ('py2', 'none', 'macosx_10_8_fat64'), ('py2', 'none', 'macosx_10_8_fat32'), ('py2', 'none', 'macosx_10_8_universal'), ('py2', 'none', 'macosx_10_7_x86_64'), ('py2', 'none', 'macosx_10_7_intel'), ('py2', 'none', 'macosx_10_7_fat64'), ('py2', 'none', 'macosx_10_7_fat32'), ('py2', 'none', 'macosx_10_7_universal'), ('py2', 'none', 'macosx_10_6_x86_64'), ('py2', 'none', 'macosx_10_6_intel'), ('py2', 'none', 'macosx_10_6_fat64'), ('py2', 'none', 'macosx_10_6_fat32'), ('py2', 'none', 'macosx_10_6_universal'), ('py2', 'none', 'macosx_10_5_x86_64'), ('py2', 'none', 'macosx_10_5_intel'), ('py2', 'none', 'macosx_10_5_fat64'), ('py2', 'none', 'macosx_10_5_fat32'), ('py2', 'none', 'macosx_10_5_universal'), ('py2', 'none', 'macosx_10_4_x86_64'), ('py2', 'none', 'macosx_10_4_intel'), ('py2', 'none', 'macosx_10_4_fat64'), ('py2', 'none', 'macosx_10_4_fat32'), ('py2', 'none', 'macosx_10_4_universal'), ('py2', 'none', 'macosx_10_3_fat32'), ('py2', 'none', 'macosx_10_3_universal'), ('py2', 'none', 'macosx_10_2_fat32'), ('py2', 'none', 'macosx_10_2_universal'), ('py2', 'none', 'macosx_10_1_fat32'), ('py2', 'none', 'macosx_10_1_universal'), ('py2', 'none', 'macosx_10_0_fat32'), ('py2', 'none', 'macosx_10_0_universal'), ('cp27', 'none', 'any'), ('cp2', 'none', 'any'), ('py27', 'none', 'any'), ('py2', 'none', 'any')]
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10ffbaf50>
pex: crawling link i=0 link=Link('file:///Users/neutronbot/.pex/build') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/datadog/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/datadog-pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpdw5BYC/datadog-0.21.0-py2-none-any.whl into distribution     pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10ff8c790>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/requests/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10ff8c790>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10ff8c790>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/decorator/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/reqpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpwAev1V/requests-2.18.4-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/decpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpuh8O7o/decorator-4.3.0-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl :: Fetching file:///Users/neutronbopex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpYTKFjt/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl ipex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x110165b50>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/certifi/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x110165b50>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/chardet/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x110165b50>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/idna/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10ff90d10>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/urllib3/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/urllibpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpg9sBTD/urllib3-1.22-py2.py3-none-any.whl into distribution   pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/chardpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp03BkXn/chardet-3.0.4-py2.py3-none-any.whl into distribution  pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/cpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp5M1QiJ/certifi-2018.4.16-py2.py3-none-any.whl into distributipex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl                                                           pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-ppex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpD5aJOS/idna-2.6-py2.py3-none-any.whl into distribution         datadog 0.21.0
simplejson 3.15.0
urllib3 1.22
chardet 3.0.4
requests 2.18.4
certifi 2018.4.16
idna 2.6
decorator 4.3.0
pex: Building pex: 1462.6ms
pex:   Resolving interpreters: 1.5ms
pex:     Setting up interpreter /Users/neutronbot/sandbox/venv/bin/python: 1.4ms
pex:   Resolving distributions: 1456.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 9.3ms
pex:       Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 8.7ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpdw5BYC/datadog-0.21.0-py2-none-any.whl into distribution: 1.8ms
pex:     Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 1.3ms
pex:       Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 0.7ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpwAev1V/requests-2.18.4-py2.py3-none-any.whl into distribution: 4.6ms
pex:     Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 1.4ms
pex:       Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 0.8ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpuh8O7o/decorator-4.3.0-py2.py3-none-any.whl into distribution: 1.2ms
pex:     Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 1.1ms
pex:       Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpYTKFjt/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution: 1.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 3.5ms
pex:       Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 2.8ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpg9sBTD/urllib3-1.22-py2.py3-none-any.whl into distribution: 2.8ms
pex:     Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 1.1ms
pex:       Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp03BkXn/chardet-3.0.4-py2.py3-none-any.whl into distribution: 1.6ms
pex:     Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 1.7ms
pex:       Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 1.2ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp5M1QiJ/certifi-2018.4.16-py2.py3-none-any.whl into distribution: 1.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpD5aJOS/idna-2.6-py2.py3-none-any.whl into distribution: 1.4ms
Running PEX file at /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp4HyVZs with args []
pex: PEX.run invoking /Users/neutronbot/sandbox/venv/bin/python /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp4HyVZs
Failed to execute PEX file, missing macosx_10_13_x86_64-cp-27-cp27m compatible dependencies for:
datadog
simplejson

interesting - the mode of two different boxes with disparate results for the same command screams "environment" to me.
does the failure mode improve at all if you add --disable-cache? if so, perhaps your ~/.pex cache got into a bad state.
beyond that, it might be useful to paste the full verbose output of the working side as an apples to apples comparison here.

--disable-cache doesn't seem to have an effect. Also I've repro'd this bug using 2.7.10, 2.7.13, and 2.7.15 on the failbox. Here's working output:
(venv) ~/sandbox/pex $ pex --version
pex 1.4.3
(venv) ~/sandbox/pex $ uname -a
Darwin Nicholass-MacBook-Pro.local 17.6.0 Darwin Kernel Version 17.6.0: Tue May  8 15:22:16 PDT 2018; root:xnu-4570.61.1~1/RELEASE_X86_64 x86_64
(venv) ~/sandbox/pex $ pex datadog -vvvvvvvvvvvvv --disable-cache
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x104052f10>
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pex: crawling link i=0 link=Link('https://pypi.python.org/simple/datadog/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/8c/a3/d3eb96a920d3ad0516f1b3924b5f2047384f2cb17b619624857edd89a82c/datadog-0.21.0.tapex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/8c/a3/d3eb96a920d3ad0516f1b3924b5f2047384f2cb17b619624857edd89a82c/datadog-0.21.0.tar.gz#sha256=67a4b7802127520f4fa84bd2bfa27d7d80b8630e03808a51f3f970069347138a :: Fetching https://files.pythonhosted.org/packages/8c/a3/d3eb96a920d3ad0516f1b3924b5f2047384f2cb17b6196pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpJkTOJW/datadog-0.21.0.tar.gz into distribution                                                                                pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpJkTOJW/datadog-0.21.0.tar.gz into distribution :: Packaging dpex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpJkTOJW/datadog-0.21.0.tar.gz into distribution :: Packaging dpex: crawling link i=0 link=Link('https://pypi.python.org/simple/requests/') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/decorator/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/49/df/50aa1999ab9bde74656c2919d9c0c085fd2b3775fd3eca826012bef76d8c/requests-2.18.4-ppex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/49/df/50aa1999ab9bde74656c2919d9c0c085fd2b3775fd3eca826012bef76d8c/requests-2.18.4-py2.py3-none-any.whl#sha256=6a1b267aa90cac58ac3a765d067950e7dbbf75b1da07e895d1f594193a40a38b :: Fetching https://files.pythonhosted.org/packages/49/df/50aa1999ab9bde74656c2919d9c0c08pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpgGwUcz/requests-2.18.4-py2.py3-none-any.whl into distribution                                                                                pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/bc/bb/a24838832ba35baf52f32ab1a49b906b5f82fb7c76b2f6a7e35e140bac30/decorator-4.3.0-ppex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/bc/bb/a24838832ba35baf52f32ab1a49b906b5f82fb7c76b2f6a7e35e140bac30/decorator-4.3.0-py2.py3-none-any.whl#sha256=2c51dff8ef3c447388fe5e4453d24a2bf128d3a4c32af3fabef1f01c6851ab82 :: Fetching https://files.pythonhosted.org/packages/bc/bb/a24838832ba35baf52f32ab1a49b906pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpVdKi4I/decorator-4.3.0-py2.py3-none-any.whl into distribution                                                                                pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/63/0c/fc416fb7a3c03f096dedbd3e1a21d5d7628288d1b885cadd70266718f355/simplejson-3.15.0pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/63/0c/fc416fb7a3c03f096dedbd3e1a21d5d7628288d1b885cadd70266718f355/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl#sha256=2fa4eafab7cb4f900ce7739129cef0da1f25acfa89089540ce6241a15a61df78 :: Fetching https://files.pythonhosted.org/packages/63/0c/fc416fb7a3c03f0pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpDfiX2G/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution                                                                                pex: crawling link i=0 link=Link('https://pypi.python.org/simple/certifi/') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/chardet/') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/idna/') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/urllib3/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/63/cb/6965947c13a94236f6d4b8223e21beb4d576dc72e8130bd7880f600839b8/urllib3-1.22-py2.pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/63/cb/6965947c13a94236f6d4b8223e21beb4d576dc72e8130bd7880f600839b8/urllib3-1.22-py2.py3-none-any.whl#sha256=06330f386d6e4b195fbfc736b297f58c5a892e4440e54d294d7004e3a9bbea1b :: Fetching https://files.pythonhosted.org/packages/63/cb/6965947c13a94236f6d4b8223e21beb4d5pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmp6oW6BQ/urllib3-1.22-py2.py3-none-any.whl into distribution                                                                                pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/bc/a9/01ffebfb562e4274b6487b4bb1ddec7ca55ec7510b22e4c51f14098443b8/chardet-3.0.4-py2pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/bc/a9/01ffebfb562e4274b6487b4bb1ddec7ca55ec7510b22e4c51f14098443b8/chardet-3.0.4-py2.py3-none-any.whl#sha256=fc323ffcaeaed0e0a02bf4d117757b98aed530d9ed4531e3e15460124c106691 :: Fetching https://files.pythonhosted.org/packages/bc/a9/01ffebfb562e4274b6487b4bb1ddec7capex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpsX6TEE/chardet-3.0.4-py2.py3-none-any.whl into distribution                                                                                pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/7c/e6/92ad559b7192d846975fc916b65f667c7b8c3a32bea7372340bfe9a15fa5/certifi-2018.4.16pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/7c/e6/92ad559b7192d846975fc916b65f667c7b8c3a32bea7372340bfe9a15fa5/certifi-2018.4.16-py2.py3-none-any.whl#sha256=9fa520c1bacfb634fa7af20a76bcbd3d5fb390481724c597da32c719a7dca4b0 :: Fetching https://files.pythonhosted.org/packages/7c/e6/92ad559b7192d846975fc916b65f6pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpsFXkK4/certifi-2018.4.16-py2.py3-none-any.whl into distribution                                                                                pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/27/cc/6dd9a3869f15c2edfab863b992838277279ce92663d334df9ecf5106f5c6/idna-2.6-py2.py3-pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/27/cc/6dd9a3869f15c2edfab863b992838277279ce92663d334df9ecf5106f5c6/idna-2.6-py2.py3-none-any.whl#sha256=8c7309c718f94b3a625cb648ace320157ad16ff131ae0af362c9f21b80ef6ec4 :: Fetching https://files.pythonhosted.org/packages/27/cc/6dd9a3869f15c2edfab863b992838277279ce9pex: Building pex :: Resolving distributions :: Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmp9XSgVb/idna-2.6-py2.py3-none-any.whl into distribution                                                                                datadog 0.21.0
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  urllib3 1.22
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  certifi 2018.4.16
  idna 2.6
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pex: Building pex: 1880.6ms
pex:   Resolving interpreters: 1.2ms
pex:     Setting up interpreter /Users/Nakis/sandbox/pex/venv/bin/python2.7: 1.2ms
pex:   Resolving distributions: 1877.0ms
pex:     Fetching https://files.pythonhosted.org/packages/8c/a3/d3eb96a920d3ad0516f1b3924b5f2047384f2cb17b619624857edd89a82c/datadog-0.21.0.tar.gz#sha256=67a4b7802127520f4fa84bd2bfa27d7d80b8630e03808a51f3f970069347138a: 48.8ms
pex:       Fetching https://files.pythonhosted.org/packages/8c/a3/d3eb96a920d3ad0516f1b3924b5f2047384f2cb17b619624857edd89a82c/datadog-0.21.0.tar.gz#sha256=67a4b7802127520f4fa84bd2bfa27d7d80b8630e03808a51f3f970069347138a: 48.1ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpJkTOJW/datadog-0.21.0.tar.gz into distribution: 508.1ms
pex:       Packaging datadog: 462.0ms
pex:         Installing /var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpgeeCIH: 459.3ms
pex:     Fetching https://files.pythonhosted.org/packages/49/df/50aa1999ab9bde74656c2919d9c0c085fd2b3775fd3eca826012bef76d8c/requests-2.18.4-py2.py3-none-any.whl#sha256=6a1b267aa90cac58ac3a765d067950e7dbbf75b1da07e895d1f594193a40a38b: 32.7ms
pex:       Fetching https://files.pythonhosted.org/packages/49/df/50aa1999ab9bde74656c2919d9c0c085fd2b3775fd3eca826012bef76d8c/requests-2.18.4-py2.py3-none-any.whl#sha256=6a1b267aa90cac58ac3a765d067950e7dbbf75b1da07e895d1f594193a40a38b: 32.0ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpgGwUcz/requests-2.18.4-py2.py3-none-any.whl into distribution: 3.7ms
pex:     Fetching https://files.pythonhosted.org/packages/bc/bb/a24838832ba35baf52f32ab1a49b906b5f82fb7c76b2f6a7e35e140bac30/decorator-4.3.0-py2.py3-none-any.whl#sha256=2c51dff8ef3c447388fe5e4453d24a2bf128d3a4c32af3fabef1f01c6851ab82: 29.7ms
pex:       Fetching https://files.pythonhosted.org/packages/bc/bb/a24838832ba35baf52f32ab1a49b906b5f82fb7c76b2f6a7e35e140bac30/decorator-4.3.0-py2.py3-none-any.whl#sha256=2c51dff8ef3c447388fe5e4453d24a2bf128d3a4c32af3fabef1f01c6851ab82: 29.1ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpVdKi4I/decorator-4.3.0-py2.py3-none-any.whl into distribution: 2.1ms
pex:     Fetching https://files.pythonhosted.org/packages/63/0c/fc416fb7a3c03f096dedbd3e1a21d5d7628288d1b885cadd70266718f355/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl#sha256=2fa4eafab7cb4f900ce7739129cef0da1f25acfa89089540ce6241a15a61df78: 38.2ms
pex:       Fetching https://files.pythonhosted.org/packages/63/0c/fc416fb7a3c03f096dedbd3e1a21d5d7628288d1b885cadd70266718f355/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl#sha256=2fa4eafab7cb4f900ce7739129cef0da1f25acfa89089540ce6241a15a61df78: 37.5ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpDfiX2G/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution: 1.6ms
pex:     Fetching https://files.pythonhosted.org/packages/63/cb/6965947c13a94236f6d4b8223e21beb4d576dc72e8130bd7880f600839b8/urllib3-1.22-py2.py3-none-any.whl#sha256=06330f386d6e4b195fbfc736b297f58c5a892e4440e54d294d7004e3a9bbea1b: 32.9ms
pex:       Fetching https://files.pythonhosted.org/packages/63/cb/6965947c13a94236f6d4b8223e21beb4d576dc72e8130bd7880f600839b8/urllib3-1.22-py2.py3-none-any.whl#sha256=06330f386d6e4b195fbfc736b297f58c5a892e4440e54d294d7004e3a9bbea1b: 32.2ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmp6oW6BQ/urllib3-1.22-py2.py3-none-any.whl into distribution: 2.4ms
pex:     Fetching https://files.pythonhosted.org/packages/bc/a9/01ffebfb562e4274b6487b4bb1ddec7ca55ec7510b22e4c51f14098443b8/chardet-3.0.4-py2.py3-none-any.whl#sha256=fc323ffcaeaed0e0a02bf4d117757b98aed530d9ed4531e3e15460124c106691: 42.0ms
pex:       Fetching https://files.pythonhosted.org/packages/bc/a9/01ffebfb562e4274b6487b4bb1ddec7ca55ec7510b22e4c51f14098443b8/chardet-3.0.4-py2.py3-none-any.whl#sha256=fc323ffcaeaed0e0a02bf4d117757b98aed530d9ed4531e3e15460124c106691: 41.4ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpsX6TEE/chardet-3.0.4-py2.py3-none-any.whl into distribution: 1.6ms
pex:     Fetching https://files.pythonhosted.org/packages/7c/e6/92ad559b7192d846975fc916b65f667c7b8c3a32bea7372340bfe9a15fa5/certifi-2018.4.16-py2.py3-none-any.whl#sha256=9fa520c1bacfb634fa7af20a76bcbd3d5fb390481724c597da32c719a7dca4b0: 38.6ms
pex:       Fetching https://files.pythonhosted.org/packages/7c/e6/92ad559b7192d846975fc916b65f667c7b8c3a32bea7372340bfe9a15fa5/certifi-2018.4.16-py2.py3-none-any.whl#sha256=9fa520c1bacfb634fa7af20a76bcbd3d5fb390481724c597da32c719a7dca4b0: 38.1ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpsFXkK4/certifi-2018.4.16-py2.py3-none-any.whl into distribution: 2.5ms
pex:     Fetching https://files.pythonhosted.org/packages/27/cc/6dd9a3869f15c2edfab863b992838277279ce92663d334df9ecf5106f5c6/idna-2.6-py2.py3-none-any.whl#sha256=8c7309c718f94b3a625cb648ace320157ad16ff131ae0af362c9f21b80ef6ec4: 27.9ms
pex:       Fetching https://files.pythonhosted.org/packages/27/cc/6dd9a3869f15c2edfab863b992838277279ce92663d334df9ecf5106f5c6/idna-2.6-py2.py3-none-any.whl#sha256=8c7309c718f94b3a625cb648ace320157ad16ff131ae0af362c9f21b80ef6ec4: 27.3ms
pex:     Translating /private/var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmp9XSgVb/idna-2.6-py2.py3-none-any.whl into distribution: 1.3ms
Running PEX file at /var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpSZJRdr with args []
pex: PEX.run invoking /Users/Nakis/sandbox/pex/venv/bin/python2.7 /var/folders/mk/bz4w0f3505190h3n4x21_jlc0000gn/T/tmpSZJRdr
Python 2.7.15 (default, May  1 2018, 16:44:08)
[GCC 4.2.1 Compatible Apple LLVM 9.1.0 (clang-902.0.39.1)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>>

Okay, in going through the output I noticed that my working box explicitly uses python2.7.
When I pass --python=/path/to/python2.7, it works where it failed before:
(venv) mapeval221:sandbox neutronbot$ pex datadog -vvvvvvvvvvvvvvvv --python=/Users/neutronbot/localpython/bin/python2.7
pex: creating PythonIdentity from id string: cp cp27m 27 2 7 15
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10acf3910>
pex: R: tags for Platform(platform='macosx_10_13_x86_64', impl='cp', version='27', abi='cp27m') x PythonInterpreter('/Users/neutronbot/localpython/bin/python2.7', PythonIdentity('CPython', 2, 7, 15), {('setuptools', '23.2.0'): '/Users/neutronbot/.pex/interpreters/CPython-2.7.15/setuptools-23.2.0-py2.7.egg', ('wheel', '0.27.0'): '/Users/neutronbot/.pex/interpreters/CPython-2.7.15/wheel-0.27.0-py2.7.egg'}) -> [('cp27', 'cp27m', 'macosx_10_13_x86_64'), ('cp27', 'cp27m', 'macosx_10_13_intel'), ('cp27', 'cp27m', 'macosx_10_13_fat64'), ('cp27', 'cp27m', 'macosx_10_13_fat32'), ('cp27', 'cp27m', 'macosx_10_13_universal'), ('cp27', 'cp27m', 'macosx_10_12_x86_64'), ('cp27', 'cp27m', 'macosx_10_12_intel'), ('cp27', 'cp27m', 'macosx_10_12_fat64'), ('cp27', 'cp27m', 'macosx_10_12_fat32'), ('cp27', 'cp27m', 'macosx_10_12_universal'), ('cp27', 'cp27m', 'macosx_10_11_x86_64'), ('cp27', 'cp27m', 'macosx_10_11_intel'), ('cp27', 'cp27m', 'macosx_10_11_fat64'), ('cp27', 'cp27m', 'macosx_10_11_fat32'), ('cp27', 'cp27m', 'macosx_10_11_universal'), ('cp27', 'cp27m', 'macosx_10_10_x86_64'), ('cp27', 'cp27m', 'macosx_10_10_intel'), ('cp27', 'cp27m', 'macosx_10_10_fat64'), ('cp27', 'cp27m', 'macosx_10_10_fat32'), ('cp27', 'cp27m', 'macosx_10_10_universal'), ('cp27', 'cp27m', 'macosx_10_9_x86_64'), ('cp27', 'cp27m', 'macosx_10_9_intel'), ('cp27', 'cp27m', 'macosx_10_9_fat64'), ('cp27', 'cp27m', 'macosx_10_9_fat32'), ('cp27', 'cp27m', 'macosx_10_9_universal'), ('cp27', 'cp27m', 'macosx_10_8_x86_64'), ('cp27', 'cp27m', 'macosx_10_8_intel'), ('cp27', 'cp27m', 'macosx_10_8_fat64'), ('cp27', 'cp27m', 'macosx_10_8_fat32'), ('cp27', 'cp27m', 'macosx_10_8_universal'), ('cp27', 'cp27m', 'macosx_10_7_x86_64'), ('cp27', 'cp27m', 'macosx_10_7_intel'), ('cp27', 'cp27m', 'macosx_10_7_fat64'), ('cp27', 'cp27m', 'macosx_10_7_fat32'), ('cp27', 'cp27m', 'macosx_10_7_universal'), ('cp27', 'cp27m', 'macosx_10_6_x86_64'), ('cp27', 'cp27m', 'macosx_10_6_intel'), ('cp27', 'cp27m', 'macosx_10_6_fat64'), ('cp27', 'cp27m', 'macosx_10_6_fat32'), ('cp27', 'cp27m', 'macosx_10_6_universal'), ('cp27', 'cp27m', 'macosx_10_5_x86_64'), ('cp27', 'cp27m', 'macosx_10_5_intel'), ('cp27', 'cp27m', 'macosx_10_5_fat64'), ('cp27', 'cp27m', 'macosx_10_5_fat32'), ('cp27', 'cp27m', 'macosx_10_5_universal'), ('cp27', 'cp27m', 'macosx_10_4_x86_64'), ('cp27', 'cp27m', 'macosx_10_4_intel'), ('cp27', 'cp27m', 'macosx_10_4_fat64'), ('cp27', 'cp27m', 'macosx_10_4_fat32'), ('cp27', 'cp27m', 'macosx_10_4_universal'), ('cp27', 'cp27m', 'macosx_10_3_fat32'), ('cp27', 'cp27m', 'macosx_10_3_universal'), ('cp27', 'cp27m', 'macosx_10_2_fat32'), ('cp27', 'cp27m', 'macosx_10_2_universal'), ('cp27', 'cp27m', 'macosx_10_1_fat32'), ('cp27', 'cp27m', 'macosx_10_1_universal'), ('cp27', 'cp27m', 'macosx_10_0_fat32'), ('cp27', 'cp27m', 'macosx_10_0_universal'), ('cp27', 'none', 'macosx_10_13_x86_64'), ('cp27', 'none', 'macosx_10_13_intel'), ('cp27', 'none', 'macosx_10_13_fat64'), ('cp27', 'none', 'macosx_10_13_fat32'), ('cp27', 'none', 'macosx_10_13_universal'), ('cp27', 'none', 'macosx_10_12_x86_64'), ('cp27', 'none', 'macosx_10_12_intel'), ('cp27', 'none', 'macosx_10_12_fat64'), ('cp27', 'none', 'macosx_10_12_fat32'), ('cp27', 'none', 'macosx_10_12_universal'), ('cp27', 'none', 'macosx_10_11_x86_64'), ('cp27', 'none', 'macosx_10_11_intel'), ('cp27', 'none', 'macosx_10_11_fat64'), ('cp27', 'none', 'macosx_10_11_fat32'), ('cp27', 'none', 'macosx_10_11_universal'), ('cp27', 'none', 'macosx_10_10_x86_64'), ('cp27', 'none', 'macosx_10_10_intel'), ('cp27', 'none', 'macosx_10_10_fat64'), ('cp27', 'none', 'macosx_10_10_fat32'), ('cp27', 'none', 'macosx_10_10_universal'), ('cp27', 'none', 'macosx_10_9_x86_64'), ('cp27', 'none', 'macosx_10_9_intel'), ('cp27', 'none', 'macosx_10_9_fat64'), ('cp27', 'none', 'macosx_10_9_fat32'), ('cp27', 'none', 'macosx_10_9_universal'), ('cp27', 'none', 'macosx_10_8_x86_64'), ('cp27', 'none', 'macosx_10_8_intel'), ('cp27', 'none', 'macosx_10_8_fat64'), ('cp27', 'none', 'macosx_10_8_fat32'), ('cp27', 'none', 'macosx_10_8_universal'), ('cp27', 'none', 'macosx_10_7_x86_64'), ('cp27', 'none', 'macosx_10_7_intel'), ('cp27', 'none', 'macosx_10_7_fat64'), ('cp27', 'none', 'macosx_10_7_fat32'), ('cp27', 'none', 'macosx_10_7_universal'), ('cp27', 'none', 'macosx_10_6_x86_64'), ('cp27', 'none', 'macosx_10_6_intel'), ('cp27', 'none', 'macosx_10_6_fat64'), ('cp27', 'none', 'macosx_10_6_fat32'), ('cp27', 'none', 'macosx_10_6_universal'), ('cp27', 'none', 'macosx_10_5_x86_64'), ('cp27', 'none', 'macosx_10_5_intel'), ('cp27', 'none', 'macosx_10_5_fat64'), ('cp27', 'none', 'macosx_10_5_fat32'), ('cp27', 'none', 'macosx_10_5_universal'), ('cp27', 'none', 'macosx_10_4_x86_64'), ('cp27', 'none', 'macosx_10_4_intel'), ('cp27', 'none', 'macosx_10_4_fat64'), ('cp27', 'none', 'macosx_10_4_fat32'), ('cp27', 'none', 'macosx_10_4_universal'), ('cp27', 'none', 'macosx_10_3_fat32'), ('cp27', 'none', 'macosx_10_3_universal'), ('cp27', 'none', 'macosx_10_2_fat32'), ('cp27', 'none', 'macosx_10_2_universal'), ('cp27', 'none', 'macosx_10_1_fat32'), ('cp27', 'none', 'macosx_10_1_universal'), ('cp27', 'none', 'macosx_10_0_fat32'), ('cp27', 'none', 'macosx_10_0_universal'), ('py2', 'none', 'macosx_10_13_x86_64'), ('py2', 'none', 'macosx_10_13_intel'), ('py2', 'none', 'macosx_10_13_fat64'), ('py2', 'none', 'macosx_10_13_fat32'), ('py2', 'none', 'macosx_10_13_universal'), ('py2', 'none', 'macosx_10_12_x86_64'), ('py2', 'none', 'macosx_10_12_intel'), ('py2', 'none', 'macosx_10_12_fat64'), ('py2', 'none', 'macosx_10_12_fat32'), ('py2', 'none', 'macosx_10_12_universal'), ('py2', 'none', 'macosx_10_11_x86_64'), ('py2', 'none', 'macosx_10_11_intel'), ('py2', 'none', 'macosx_10_11_fat64'), ('py2', 'none', 'macosx_10_11_fat32'), ('py2', 'none', 'macosx_10_11_universal'), ('py2', 'none', 'macosx_10_10_x86_64'), ('py2', 'none', 'macosx_10_10_intel'), ('py2', 'none', 'macosx_10_10_fat64'), ('py2', 'none', 'macosx_10_10_fat32'), ('py2', 'none', 'macosx_10_10_universal'), ('py2', 'none', 'macosx_10_9_x86_64'), ('py2', 'none', 'macosx_10_9_intel'), ('py2', 'none', 'macosx_10_9_fat64'), ('py2', 'none', 'macosx_10_9_fat32'), ('py2', 'none', 'macosx_10_9_universal'), ('py2', 'none', 'macosx_10_8_x86_64'), ('py2', 'none', 'macosx_10_8_intel'), ('py2', 'none', 'macosx_10_8_fat64'), ('py2', 'none', 'macosx_10_8_fat32'), ('py2', 'none', 'macosx_10_8_universal'), ('py2', 'none', 'macosx_10_7_x86_64'), ('py2', 'none', 'macosx_10_7_intel'), ('py2', 'none', 'macosx_10_7_fat64'), ('py2', 'none', 'macosx_10_7_fat32'), ('py2', 'none', 'macosx_10_7_universal'), ('py2', 'none', 'macosx_10_6_x86_64'), ('py2', 'none', 'macosx_10_6_intel'), ('py2', 'none', 'macosx_10_6_fat64'), ('py2', 'none', 'macosx_10_6_fat32'), ('py2', 'none', 'macosx_10_6_universal'), ('py2', 'none', 'macosx_10_5_x86_64'), ('py2', 'none', 'macosx_10_5_intel'), ('py2', 'none', 'macosx_10_5_fat64'), ('py2', 'none', 'macosx_10_5_fat32'), ('py2', 'none', 'macosx_10_5_universal'), ('py2', 'none', 'macosx_10_4_x86_64'), ('py2', 'none', 'macosx_10_4_intel'), ('py2', 'none', 'macosx_10_4_fat64'), ('py2', 'none', 'macosx_10_4_fat32'), ('py2', 'none', 'macosx_10_4_universal'), ('py2', 'none', 'macosx_10_3_fat32'), ('py2', 'none', 'macosx_10_3_universal'), ('py2', 'none', 'macosx_10_2_fat32'), ('py2', 'none', 'macosx_10_2_universal'), ('py2', 'none', 'macosx_10_1_fat32'), ('py2', 'none', 'macosx_10_1_universal'), ('py2', 'none', 'macosx_10_0_fat32'), ('py2', 'none', 'macosx_10_0_universal'), ('cp27', 'none', 'any'), ('cp2', 'none', 'any'), ('py27', 'none', 'any'), ('py2', 'none', 'any')]
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10ace85d0>
pex: crawling link i=0 link=Link('file:///Users/neutronbot/.pex/build') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/datadog/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/datadog-pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpebQydg/datadog-0.21.0-py2-none-any.whl into distribution     pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10acbfcd0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/requests/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10acf33d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10acbfdd0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/decorator/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/reqpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpLvEQtv/requests-2.18.4-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/decpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp86tOW0/decorator-4.3.0-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl :: Fetching file:///Users/neutronbopex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpfGcaIw/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl ipex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10afc62d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/certifi/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10afc62d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/chardet/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10afc62d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/idna/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10c816490>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/urllib3/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/urllibpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp3CBGws/urllib3-1.22-py2.py3-none-any.whl into distribution   pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/chardpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpMbB3YL/chardet-3.0.4-py2.py3-none-any.whl into distribution  pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/cpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpAEhbnK/certifi-2018.4.16-py2.py3-none-any.whl into distributipex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl                                                           pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-ppex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp5jw5Rj/idna-2.6-py2.py3-none-any.whl into distribution         datadog 0.21.0
  simplejson 3.15.0
  urllib3 1.22
  chardet 3.0.4
  requests 2.18.4
  certifi 2018.4.16
  idna 2.6
  decorator 4.3.0
pex: Building pex: 1478.2ms
pex:   Resolving interpreters: 32.2ms
pex:     Setting up interpreter /Users/neutronbot/localpython/bin/python2.7: 3.6ms
pex:   Resolving distributions: 1440.9ms
pex:     Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 7.4ms
pex:       Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 6.9ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpebQydg/datadog-0.21.0-py2-none-any.whl into distribution: 3.0ms
pex:     Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 1.2ms
pex:       Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 0.7ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpLvEQtv/requests-2.18.4-py2.py3-none-any.whl into distribution: 4.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp86tOW0/decorator-4.3.0-py2.py3-none-any.whl into distribution: 1.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpfGcaIw/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution: 1.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 1.3ms
pex:       Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 0.7ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp3CBGws/urllib3-1.22-py2.py3-none-any.whl into distribution: 3.9ms
pex:     Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 1.1ms
pex:       Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpMbB3YL/chardet-3.0.4-py2.py3-none-any.whl into distribution: 1.7ms
pex:     Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 1.1ms
pex:       Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpAEhbnK/certifi-2018.4.16-py2.py3-none-any.whl into distribution: 1.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp5jw5Rj/idna-2.6-py2.py3-none-any.whl into distribution: 2.2ms
Running PEX file at /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpbBgdfR with args []
pex: PEX.run invoking /Users/neutronbot/localpython/bin/python2.7 /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpbBgdfR
Python 2.7.15 (default, Jun  7 2018, 12:50:09)
[GCC 4.2.1 Compatible Apple LLVM 9.1.0 (clang-902.0.39.2)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>>

Okay, seems to be something to do with the Python version.
What python does pex use by default? I assumed it was the first python on my PATH, but it seems to fail unless I explicitly pass it, e.g.:
(venv) neutronbot$ which python
/Users/neutronbot/localpython/bin/python
(venv) neutronbot$ pex datadog -vvvvvvvvvvvvvvvv
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x103989610>
pex: R: tags for Platform(platform='macosx_10_13_x86_64', impl='cp', version='27', abi='cp27m') x PythonInterpreter('/Users/neutronbot/sandbox/venv/bin/python', PythonIdentity('CPython', 2, 7, 10), {('python', '2.7.10'): '/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/lib-dynload', ('pip', '10.0.1'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('ipython-genutils', '0.2.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('enum34', '1.1.6'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('ptyprocess', '0.5.2'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('decorator', '4.3.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('backports.shutil-get-terminal-size', '1.0.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('six', '1.11.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('setuptools', '33.1.1'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('wheel', '0.29.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('wsgiref', '0.1.2'): '/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7', ('pex', '1.4.3'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('appnope', '0.1.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('pexpect', '4.6.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('simplegeneric', '0.8.1'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('traitlets', '4.3.2'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('pygments', '2.2.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages'}) -> [('cp27', 'cp27m', 'macosx_10_13_x86_64'), ('cp27', 'cp27m', 'macosx_10_13_intel'), ('cp27', 'cp27m', 'macosx_10_13_fat64'), ('cp27', 'cp27m', 'macosx_10_13_fat32'), ('cp27', 'cp27m', 'macosx_10_13_universal'), ('cp27', 'cp27m', 'macosx_10_12_x86_64'), ('cp27', 'cp27m', 'macosx_10_12_intel'), ('cp27', 'cp27m', 'macosx_10_12_fat64'), ('cp27', 'cp27m', 'macosx_10_12_fat32'), ('cp27', 'cp27m', 'macosx_10_12_universal'), ('cp27', 'cp27m', 'macosx_10_11_x86_64'), ('cp27', 'cp27m', 'macosx_10_11_intel'), ('cp27', 'cp27m', 'macosx_10_11_fat64'), ('cp27', 'cp27m', 'macosx_10_11_fat32'), ('cp27', 'cp27m', 'macosx_10_11_universal'), ('cp27', 'cp27m', 'macosx_10_10_x86_64'), ('cp27', 'cp27m', 'macosx_10_10_intel'), ('cp27', 'cp27m', 'macosx_10_10_fat64'), ('cp27', 'cp27m', 'macosx_10_10_fat32'), ('cp27', 'cp27m', 'macosx_10_10_universal'), ('cp27', 'cp27m', 'macosx_10_9_x86_64'), ('cp27', 'cp27m', 'macosx_10_9_intel'), ('cp27', 'cp27m', 'macosx_10_9_fat64'), ('cp27', 'cp27m', 'macosx_10_9_fat32'), ('cp27', 'cp27m', 'macosx_10_9_universal'), ('cp27', 'cp27m', 'macosx_10_8_x86_64'), ('cp27', 'cp27m', 'macosx_10_8_intel'), ('cp27', 'cp27m', 'macosx_10_8_fat64'), ('cp27', 'cp27m', 'macosx_10_8_fat32'), ('cp27', 'cp27m', 'macosx_10_8_universal'), ('cp27', 'cp27m', 'macosx_10_7_x86_64'), ('cp27', 'cp27m', 'macosx_10_7_intel'), ('cp27', 'cp27m', 'macosx_10_7_fat64'), ('cp27', 'cp27m', 'macosx_10_7_fat32'), ('cp27', 'cp27m', 'macosx_10_7_universal'), ('cp27', 'cp27m', 'macosx_10_6_x86_64'), ('cp27', 'cp27m', 'macosx_10_6_intel'), ('cp27', 'cp27m', 'macosx_10_6_fat64'), ('cp27', 'cp27m', 'macosx_10_6_fat32'), ('cp27', 'cp27m', 'macosx_10_6_universal'), ('cp27', 'cp27m', 'macosx_10_5_x86_64'), ('cp27', 'cp27m', 'macosx_10_5_intel'), ('cp27', 'cp27m', 'macosx_10_5_fat64'), ('cp27', 'cp27m', 'macosx_10_5_fat32'), ('cp27', 'cp27m', 'macosx_10_5_universal'), ('cp27', 'cp27m', 'macosx_10_4_x86_64'), ('cp27', 'cp27m', 'macosx_10_4_intel'), ('cp27', 'cp27m', 'macosx_10_4_fat64'), ('cp27', 'cp27m', 'macosx_10_4_fat32'), ('cp27', 'cp27m', 'macosx_10_4_universal'), ('cp27', 'cp27m', 'macosx_10_3_fat32'), ('cp27', 'cp27m', 'macosx_10_3_universal'), ('cp27', 'cp27m', 'macosx_10_2_fat32'), ('cp27', 'cp27m', 'macosx_10_2_universal'), ('cp27', 'cp27m', 'macosx_10_1_fat32'), ('cp27', 'cp27m', 'macosx_10_1_universal'), ('cp27', 'cp27m', 'macosx_10_0_fat32'), ('cp27', 'cp27m', 'macosx_10_0_universal'), ('cp27', 'none', 'macosx_10_13_x86_64'), ('cp27', 'none', 'macosx_10_13_intel'), ('cp27', 'none', 'macosx_10_13_fat64'), ('cp27', 'none', 'macosx_10_13_fat32'), ('cp27', 'none', 'macosx_10_13_universal'), ('cp27', 'none', 'macosx_10_12_x86_64'), ('cp27', 'none', 'macosx_10_12_intel'), ('cp27', 'none', 'macosx_10_12_fat64'), ('cp27', 'none', 'macosx_10_12_fat32'), ('cp27', 'none', 'macosx_10_12_universal'), ('cp27', 'none', 'macosx_10_11_x86_64'), ('cp27', 'none', 'macosx_10_11_intel'), ('cp27', 'none', 'macosx_10_11_fat64'), ('cp27', 'none', 'macosx_10_11_fat32'), ('cp27', 'none', 'macosx_10_11_universal'), ('cp27', 'none', 'macosx_10_10_x86_64'), ('cp27', 'none', 'macosx_10_10_intel'), ('cp27', 'none', 'macosx_10_10_fat64'), ('cp27', 'none', 'macosx_10_10_fat32'), ('cp27', 'none', 'macosx_10_10_universal'), ('cp27', 'none', 'macosx_10_9_x86_64'), ('cp27', 'none', 'macosx_10_9_intel'), ('cp27', 'none', 'macosx_10_9_fat64'), ('cp27', 'none', 'macosx_10_9_fat32'), ('cp27', 'none', 'macosx_10_9_universal'), ('cp27', 'none', 'macosx_10_8_x86_64'), ('cp27', 'none', 'macosx_10_8_intel'), ('cp27', 'none', 'macosx_10_8_fat64'), ('cp27', 'none', 'macosx_10_8_fat32'), ('cp27', 'none', 'macosx_10_8_universal'), ('cp27', 'none', 'macosx_10_7_x86_64'), ('cp27', 'none', 'macosx_10_7_intel'), ('cp27', 'none', 'macosx_10_7_fat64'), ('cp27', 'none', 'macosx_10_7_fat32'), ('cp27', 'none', 'macosx_10_7_universal'), ('cp27', 'none', 'macosx_10_6_x86_64'), ('cp27', 'none', 'macosx_10_6_intel'), ('cp27', 'none', 'macosx_10_6_fat64'), ('cp27', 'none', 'macosx_10_6_fat32'), ('cp27', 'none', 'macosx_10_6_universal'), ('cp27', 'none', 'macosx_10_5_x86_64'), ('cp27', 'none', 'macosx_10_5_intel'), ('cp27', 'none', 'macosx_10_5_fat64'), ('cp27', 'none', 'macosx_10_5_fat32'), ('cp27', 'none', 'macosx_10_5_universal'), ('cp27', 'none', 'macosx_10_4_x86_64'), ('cp27', 'none', 'macosx_10_4_intel'), ('cp27', 'none', 'macosx_10_4_fat64'), ('cp27', 'none', 'macosx_10_4_fat32'), ('cp27', 'none', 'macosx_10_4_universal'), ('cp27', 'none', 'macosx_10_3_fat32'), ('cp27', 'none', 'macosx_10_3_universal'), ('cp27', 'none', 'macosx_10_2_fat32'), ('cp27', 'none', 'macosx_10_2_universal'), ('cp27', 'none', 'macosx_10_1_fat32'), ('cp27', 'none', 'macosx_10_1_universal'), ('cp27', 'none', 'macosx_10_0_fat32'), ('cp27', 'none', 'macosx_10_0_universal'), ('py2', 'none', 'macosx_10_13_x86_64'), ('py2', 'none', 'macosx_10_13_intel'), ('py2', 'none', 'macosx_10_13_fat64'), ('py2', 'none', 'macosx_10_13_fat32'), ('py2', 'none', 'macosx_10_13_universal'), ('py2', 'none', 'macosx_10_12_x86_64'), ('py2', 'none', 'macosx_10_12_intel'), ('py2', 'none', 'macosx_10_12_fat64'), ('py2', 'none', 'macosx_10_12_fat32'), ('py2', 'none', 'macosx_10_12_universal'), ('py2', 'none', 'macosx_10_11_x86_64'), ('py2', 'none', 'macosx_10_11_intel'), ('py2', 'none', 'macosx_10_11_fat64'), ('py2', 'none', 'macosx_10_11_fat32'), ('py2', 'none', 'macosx_10_11_universal'), ('py2', 'none', 'macosx_10_10_x86_64'), ('py2', 'none', 'macosx_10_10_intel'), ('py2', 'none', 'macosx_10_10_fat64'), ('py2', 'none', 'macosx_10_10_fat32'), ('py2', 'none', 'macosx_10_10_universal'), ('py2', 'none', 'macosx_10_9_x86_64'), ('py2', 'none', 'macosx_10_9_intel'), ('py2', 'none', 'macosx_10_9_fat64'), ('py2', 'none', 'macosx_10_9_fat32'), ('py2', 'none', 'macosx_10_9_universal'), ('py2', 'none', 'macosx_10_8_x86_64'), ('py2', 'none', 'macosx_10_8_intel'), ('py2', 'none', 'macosx_10_8_fat64'), ('py2', 'none', 'macosx_10_8_fat32'), ('py2', 'none', 'macosx_10_8_universal'), ('py2', 'none', 'macosx_10_7_x86_64'), ('py2', 'none', 'macosx_10_7_intel'), ('py2', 'none', 'macosx_10_7_fat64'), ('py2', 'none', 'macosx_10_7_fat32'), ('py2', 'none', 'macosx_10_7_universal'), ('py2', 'none', 'macosx_10_6_x86_64'), ('py2', 'none', 'macosx_10_6_intel'), ('py2', 'none', 'macosx_10_6_fat64'), ('py2', 'none', 'macosx_10_6_fat32'), ('py2', 'none', 'macosx_10_6_universal'), ('py2', 'none', 'macosx_10_5_x86_64'), ('py2', 'none', 'macosx_10_5_intel'), ('py2', 'none', 'macosx_10_5_fat64'), ('py2', 'none', 'macosx_10_5_fat32'), ('py2', 'none', 'macosx_10_5_universal'), ('py2', 'none', 'macosx_10_4_x86_64'), ('py2', 'none', 'macosx_10_4_intel'), ('py2', 'none', 'macosx_10_4_fat64'), ('py2', 'none', 'macosx_10_4_fat32'), ('py2', 'none', 'macosx_10_4_universal'), ('py2', 'none', 'macosx_10_3_fat32'), ('py2', 'none', 'macosx_10_3_universal'), ('py2', 'none', 'macosx_10_2_fat32'), ('py2', 'none', 'macosx_10_2_universal'), ('py2', 'none', 'macosx_10_1_fat32'), ('py2', 'none', 'macosx_10_1_universal'), ('py2', 'none', 'macosx_10_0_fat32'), ('py2', 'none', 'macosx_10_0_universal'), ('cp27', 'none', 'any'), ('cp2', 'none', 'any'), ('py27', 'none', 'any'), ('py2', 'none', 'any')]
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x103989f50>
pex: crawling link i=0 link=Link('file:///Users/neutronbot/.pex/build') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/datadog/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/datadog-pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpNAosCD/datadog-0.21.0-py2-none-any.whl into distribution     pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10395a790>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/requests/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10395a790>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10395a790>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/decorator/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/reqpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpNg1imd/requests-2.18.4-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/decpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpKajNeV/decorator-4.3.0-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl :: Fetching file:///Users/neutronbopex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpCRl6kl/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl ipex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105343b50>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/certifi/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105343b50>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/chardet/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x105343b50>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/idna/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x1039e5d10>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/urllib3/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/urllibpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmprx6qCa/urllib3-1.22-py2.py3-none-any.whl into distribution   pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/chardpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp9S6vez/chardet-3.0.4-py2.py3-none-any.whl into distribution  pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/cpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpnY9_u5/certifi-2018.4.16-py2.py3-none-any.whl into distributipex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl                                                           pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-ppex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmprA2ol9/idna-2.6-py2.py3-none-any.whl into distribution         datadog 0.21.0
  simplejson 3.15.0
  urllib3 1.22
  chardet 3.0.4
  requests 2.18.4
  certifi 2018.4.16
  idna 2.6
  decorator 4.3.0
pex: Building pex: 1413.2ms
pex:   Resolving interpreters: 1.5ms
pex:     Setting up interpreter /Users/neutronbot/sandbox/venv/bin/python: 1.5ms
pex:   Resolving distributions: 1407.3ms
pex:     Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 7.3ms
pex:       Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 6.8ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpNAosCD/datadog-0.21.0-py2-none-any.whl into distribution: 2.8ms
pex:     Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 1.4ms
pex:       Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpNg1imd/requests-2.18.4-py2.py3-none-any.whl into distribution: 4.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpKajNeV/decorator-4.3.0-py2.py3-none-any.whl into distribution: 1.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpCRl6kl/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution: 1.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 1.3ms
pex:       Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmprx6qCa/urllib3-1.22-py2.py3-none-any.whl into distribution: 3.9ms
pex:     Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 1.2ms
pex:       Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp9S6vez/chardet-3.0.4-py2.py3-none-any.whl into distribution: 1.6ms
pex:     Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 1.1ms
pex:       Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpnY9_u5/certifi-2018.4.16-py2.py3-none-any.whl into distribution: 1.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmprA2ol9/idna-2.6-py2.py3-none-any.whl into distribution: 1.6ms
Running PEX file at /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpTOrLgA with args []
pex: PEX.run invoking /Users/neutronbot/sandbox/venv/bin/python /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpTOrLgA
Failed to execute PEX file, missing macosx_10_13_x86_64-cp-27-cp27m compatible dependencies for:
datadog
simplejson
(venv) neutronbot$ pex datadog -vvvvvvvvvvvvvvvv --python=/Users/neutronbot/localpython/bin/python
pex: creating PythonIdentity from id string: cp cp27m 27 2 7 15
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10355c910>
pex: R: tags for Platform(platform='macosx_10_13_x86_64', impl='cp', version='27', abi='cp27m') x PythonInterpreter('/Users/neutronbot/localpython/bin/python2.7', PythonIdentity('CPython', 2, 7, 15), {('setuptools', '23.2.0'): '/Users/neutronbot/.pex/interpreters/CPython-2.7.15/setuptools-23.2.0-py2.7.egg', ('wheel', '0.27.0'): '/Users/neutronbot/.pex/interpreters/CPython-2.7.15/wheel-0.27.0-py2.7.egg'}) -> [('cp27', 'cp27m', 'macosx_10_13_x86_64'), ('cp27', 'cp27m', 'macosx_10_13_intel'), ('cp27', 'cp27m', 'macosx_10_13_fat64'), ('cp27', 'cp27m', 'macosx_10_13_fat32'), ('cp27', 'cp27m', 'macosx_10_13_universal'), ('cp27', 'cp27m', 'macosx_10_12_x86_64'), ('cp27', 'cp27m', 'macosx_10_12_intel'), ('cp27', 'cp27m', 'macosx_10_12_fat64'), ('cp27', 'cp27m', 'macosx_10_12_fat32'), ('cp27', 'cp27m', 'macosx_10_12_universal'), ('cp27', 'cp27m', 'macosx_10_11_x86_64'), ('cp27', 'cp27m', 'macosx_10_11_intel'), ('cp27', 'cp27m', 'macosx_10_11_fat64'), ('cp27', 'cp27m', 'macosx_10_11_fat32'), ('cp27', 'cp27m', 'macosx_10_11_universal'), ('cp27', 'cp27m', 'macosx_10_10_x86_64'), ('cp27', 'cp27m', 'macosx_10_10_intel'), ('cp27', 'cp27m', 'macosx_10_10_fat64'), ('cp27', 'cp27m', 'macosx_10_10_fat32'), ('cp27', 'cp27m', 'macosx_10_10_universal'), ('cp27', 'cp27m', 'macosx_10_9_x86_64'), ('cp27', 'cp27m', 'macosx_10_9_intel'), ('cp27', 'cp27m', 'macosx_10_9_fat64'), ('cp27', 'cp27m', 'macosx_10_9_fat32'), ('cp27', 'cp27m', 'macosx_10_9_universal'), ('cp27', 'cp27m', 'macosx_10_8_x86_64'), ('cp27', 'cp27m', 'macosx_10_8_intel'), ('cp27', 'cp27m', 'macosx_10_8_fat64'), ('cp27', 'cp27m', 'macosx_10_8_fat32'), ('cp27', 'cp27m', 'macosx_10_8_universal'), ('cp27', 'cp27m', 'macosx_10_7_x86_64'), ('cp27', 'cp27m', 'macosx_10_7_intel'), ('cp27', 'cp27m', 'macosx_10_7_fat64'), ('cp27', 'cp27m', 'macosx_10_7_fat32'), ('cp27', 'cp27m', 'macosx_10_7_universal'), ('cp27', 'cp27m', 'macosx_10_6_x86_64'), ('cp27', 'cp27m', 'macosx_10_6_intel'), ('cp27', 'cp27m', 'macosx_10_6_fat64'), ('cp27', 'cp27m', 'macosx_10_6_fat32'), ('cp27', 'cp27m', 'macosx_10_6_universal'), ('cp27', 'cp27m', 'macosx_10_5_x86_64'), ('cp27', 'cp27m', 'macosx_10_5_intel'), ('cp27', 'cp27m', 'macosx_10_5_fat64'), ('cp27', 'cp27m', 'macosx_10_5_fat32'), ('cp27', 'cp27m', 'macosx_10_5_universal'), ('cp27', 'cp27m', 'macosx_10_4_x86_64'), ('cp27', 'cp27m', 'macosx_10_4_intel'), ('cp27', 'cp27m', 'macosx_10_4_fat64'), ('cp27', 'cp27m', 'macosx_10_4_fat32'), ('cp27', 'cp27m', 'macosx_10_4_universal'), ('cp27', 'cp27m', 'macosx_10_3_fat32'), ('cp27', 'cp27m', 'macosx_10_3_universal'), ('cp27', 'cp27m', 'macosx_10_2_fat32'), ('cp27', 'cp27m', 'macosx_10_2_universal'), ('cp27', 'cp27m', 'macosx_10_1_fat32'), ('cp27', 'cp27m', 'macosx_10_1_universal'), ('cp27', 'cp27m', 'macosx_10_0_fat32'), ('cp27', 'cp27m', 'macosx_10_0_universal'), ('cp27', 'none', 'macosx_10_13_x86_64'), ('cp27', 'none', 'macosx_10_13_intel'), ('cp27', 'none', 'macosx_10_13_fat64'), ('cp27', 'none', 'macosx_10_13_fat32'), ('cp27', 'none', 'macosx_10_13_universal'), ('cp27', 'none', 'macosx_10_12_x86_64'), ('cp27', 'none', 'macosx_10_12_intel'), ('cp27', 'none', 'macosx_10_12_fat64'), ('cp27', 'none', 'macosx_10_12_fat32'), ('cp27', 'none', 'macosx_10_12_universal'), ('cp27', 'none', 'macosx_10_11_x86_64'), ('cp27', 'none', 'macosx_10_11_intel'), ('cp27', 'none', 'macosx_10_11_fat64'), ('cp27', 'none', 'macosx_10_11_fat32'), ('cp27', 'none', 'macosx_10_11_universal'), ('cp27', 'none', 'macosx_10_10_x86_64'), ('cp27', 'none', 'macosx_10_10_intel'), ('cp27', 'none', 'macosx_10_10_fat64'), ('cp27', 'none', 'macosx_10_10_fat32'), ('cp27', 'none', 'macosx_10_10_universal'), ('cp27', 'none', 'macosx_10_9_x86_64'), ('cp27', 'none', 'macosx_10_9_intel'), ('cp27', 'none', 'macosx_10_9_fat64'), ('cp27', 'none', 'macosx_10_9_fat32'), ('cp27', 'none', 'macosx_10_9_universal'), ('cp27', 'none', 'macosx_10_8_x86_64'), ('cp27', 'none', 'macosx_10_8_intel'), ('cp27', 'none', 'macosx_10_8_fat64'), ('cp27', 'none', 'macosx_10_8_fat32'), ('cp27', 'none', 'macosx_10_8_universal'), ('cp27', 'none', 'macosx_10_7_x86_64'), ('cp27', 'none', 'macosx_10_7_intel'), ('cp27', 'none', 'macosx_10_7_fat64'), ('cp27', 'none', 'macosx_10_7_fat32'), ('cp27', 'none', 'macosx_10_7_universal'), ('cp27', 'none', 'macosx_10_6_x86_64'), ('cp27', 'none', 'macosx_10_6_intel'), ('cp27', 'none', 'macosx_10_6_fat64'), ('cp27', 'none', 'macosx_10_6_fat32'), ('cp27', 'none', 'macosx_10_6_universal'), ('cp27', 'none', 'macosx_10_5_x86_64'), ('cp27', 'none', 'macosx_10_5_intel'), ('cp27', 'none', 'macosx_10_5_fat64'), ('cp27', 'none', 'macosx_10_5_fat32'), ('cp27', 'none', 'macosx_10_5_universal'), ('cp27', 'none', 'macosx_10_4_x86_64'), ('cp27', 'none', 'macosx_10_4_intel'), ('cp27', 'none', 'macosx_10_4_fat64'), ('cp27', 'none', 'macosx_10_4_fat32'), ('cp27', 'none', 'macosx_10_4_universal'), ('cp27', 'none', 'macosx_10_3_fat32'), ('cp27', 'none', 'macosx_10_3_universal'), ('cp27', 'none', 'macosx_10_2_fat32'), ('cp27', 'none', 'macosx_10_2_universal'), ('cp27', 'none', 'macosx_10_1_fat32'), ('cp27', 'none', 'macosx_10_1_universal'), ('cp27', 'none', 'macosx_10_0_fat32'), ('cp27', 'none', 'macosx_10_0_universal'), ('py2', 'none', 'macosx_10_13_x86_64'), ('py2', 'none', 'macosx_10_13_intel'), ('py2', 'none', 'macosx_10_13_fat64'), ('py2', 'none', 'macosx_10_13_fat32'), ('py2', 'none', 'macosx_10_13_universal'), ('py2', 'none', 'macosx_10_12_x86_64'), ('py2', 'none', 'macosx_10_12_intel'), ('py2', 'none', 'macosx_10_12_fat64'), ('py2', 'none', 'macosx_10_12_fat32'), ('py2', 'none', 'macosx_10_12_universal'), ('py2', 'none', 'macosx_10_11_x86_64'), ('py2', 'none', 'macosx_10_11_intel'), ('py2', 'none', 'macosx_10_11_fat64'), ('py2', 'none', 'macosx_10_11_fat32'), ('py2', 'none', 'macosx_10_11_universal'), ('py2', 'none', 'macosx_10_10_x86_64'), ('py2', 'none', 'macosx_10_10_intel'), ('py2', 'none', 'macosx_10_10_fat64'), ('py2', 'none', 'macosx_10_10_fat32'), ('py2', 'none', 'macosx_10_10_universal'), ('py2', 'none', 'macosx_10_9_x86_64'), ('py2', 'none', 'macosx_10_9_intel'), ('py2', 'none', 'macosx_10_9_fat64'), ('py2', 'none', 'macosx_10_9_fat32'), ('py2', 'none', 'macosx_10_9_universal'), ('py2', 'none', 'macosx_10_8_x86_64'), ('py2', 'none', 'macosx_10_8_intel'), ('py2', 'none', 'macosx_10_8_fat64'), ('py2', 'none', 'macosx_10_8_fat32'), ('py2', 'none', 'macosx_10_8_universal'), ('py2', 'none', 'macosx_10_7_x86_64'), ('py2', 'none', 'macosx_10_7_intel'), ('py2', 'none', 'macosx_10_7_fat64'), ('py2', 'none', 'macosx_10_7_fat32'), ('py2', 'none', 'macosx_10_7_universal'), ('py2', 'none', 'macosx_10_6_x86_64'), ('py2', 'none', 'macosx_10_6_intel'), ('py2', 'none', 'macosx_10_6_fat64'), ('py2', 'none', 'macosx_10_6_fat32'), ('py2', 'none', 'macosx_10_6_universal'), ('py2', 'none', 'macosx_10_5_x86_64'), ('py2', 'none', 'macosx_10_5_intel'), ('py2', 'none', 'macosx_10_5_fat64'), ('py2', 'none', 'macosx_10_5_fat32'), ('py2', 'none', 'macosx_10_5_universal'), ('py2', 'none', 'macosx_10_4_x86_64'), ('py2', 'none', 'macosx_10_4_intel'), ('py2', 'none', 'macosx_10_4_fat64'), ('py2', 'none', 'macosx_10_4_fat32'), ('py2', 'none', 'macosx_10_4_universal'), ('py2', 'none', 'macosx_10_3_fat32'), ('py2', 'none', 'macosx_10_3_universal'), ('py2', 'none', 'macosx_10_2_fat32'), ('py2', 'none', 'macosx_10_2_universal'), ('py2', 'none', 'macosx_10_1_fat32'), ('py2', 'none', 'macosx_10_1_universal'), ('py2', 'none', 'macosx_10_0_fat32'), ('py2', 'none', 'macosx_10_0_universal'), ('cp27', 'none', 'any'), ('cp2', 'none', 'any'), ('py27', 'none', 'any'), ('py2', 'none', 'any')]
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x1035515d0>
pex: crawling link i=0 link=Link('file:///Users/neutronbot/.pex/build') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/datadog/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/datadog-pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmprAAK0v/datadog-0.21.0-py2-none-any.whl into distribution     pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x103528cd0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/requests/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10355c3d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10355c3d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/decorator/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/reqpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp_28VFk/requests-2.18.4-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/decpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpHLSQxH/decorator-4.3.0-py2.py3-none-any.whl into distributionpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl :: Fetching file:///Users/neutronbopex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpH4hKKd/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl ipex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10382f2d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/certifi/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10382f2d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/chardet/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10382f2d0>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/idna/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10385a490>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/urllib3/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/urllibpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpURIMsI/urllib3-1.22-py2.py3-none-any.whl into distribution   pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/chardpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpbmxQa4/chardet-3.0.4-py2.py3-none-any.whl into distribution  pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/cpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpiVtf9o/certifi-2018.4.16-py2.py3-none-any.whl into distributipex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl                                                           pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6-ppex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpe1N21M/idna-2.6-py2.py3-none-any.whl into distribution         datadog 0.21.0
  simplejson 3.15.0
  urllib3 1.22
  chardet 3.0.4
  requests 2.18.4
  certifi 2018.4.16
  idna 2.6
  decorator 4.3.0
pex: Building pex: 1444.7ms
pex:   Resolving interpreters: 32.5ms
pex:     Setting up interpreter /Users/neutronbot/localpython/bin/python2.7: 3.6ms
pex:   Resolving distributions: 1407.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 8.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0-py2-none-any.whl: 7.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmprAAK0v/datadog-0.21.0-py2-none-any.whl into distribution: 3.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 1.2ms
pex:       Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp_28VFk/requests-2.18.4-py2.py3-none-any.whl into distribution: 4.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0-py2.py3-none-any.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpHLSQxH/decorator-4.3.0-py2.py3-none-any.whl into distribution: 1.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpH4hKKd/simplejson-3.15.0-cp27-cp27m-macosx_10_12_x86_64.whl into distribution: 1.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 1.4ms
pex:       Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22-py2.py3-none-any.whl: 0.7ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpURIMsI/urllib3-1.22-py2.py3-none-any.whl into distribution: 3.9ms
pex:     Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 1.1ms
pex:       Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpbmxQa4/chardet-3.0.4-py2.py3-none-any.whl into distribution: 1.7ms
pex:     Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 1.1ms
pex:       Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16-py2.py3-none-any.whl: 0.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpiVtf9o/certifi-2018.4.16-py2.py3-none-any.whl into distribution: 1.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 1.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/idna-2.6-py2.py3-none-any.whl: 0.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpe1N21M/idna-2.6-py2.py3-none-any.whl into distribution: 2.3ms
Running PEX file at /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpcdCof4 with args []
pex: PEX.run invoking /Users/neutronbot/localpython/bin/python2.7 /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpcdCof4
Python 2.7.15 (default, Jun  7 2018, 12:50:09)
[GCC 4.2.1 Compatible Apple LLVM 9.1.0 (clang-902.0.39.2)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>>

I have a hunch that the variation is due to setuptools/wheel versions coming along with each interpreter. In Pant's usage of pex, we scrub the system setuptools, wheel and any other site packages and install our own. Pretty wild hunch, but I did just Wade through similarly variable results upgrading pants to pex 1.4.3 from 1.3.2. The full verbose logs here help a ton and I think I have enough to setup a repro, and if successful, a fix.

@jsirois After some further investigation (building Python from source and also installing via pyenv) I'm pretty sure it's not version dependent (I've gotten things working with 2.7.10 multiple times) but has something to do with using MacOS System Python

@DrumMachineLearning I think @jsirois is talking about the setuptools version vs the python version. can you check the setuptools versions in the working vs non-working envs and see if aligning those improves things at all?

FWIW I have a repro - on linux, trying to narrow it down.

I've repro'd (one working, one not) using fresh virtualenvs on each box.
Both are running setuptools 33.1.1
Interestingly enough, passing system python (i.e. pex datadog -vvvvvvvvvvvvvvvvvv --python=/usr/bin/python) causes the working box to fail.

And here's another interesting datapoint- when you force pex to build, everything works fine.
On the failbox:
(venv) neutronbot$ pex datadog -vvvvvvvvvvvvvvvvvvvvvvv --no-wheel
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10af78190>
pex: R: tags for Platform(platform='macosx_10_13_x86_64', impl='cp', version='27', abi='cp27m') x PythonInterpreter('/Users/neutronbot/sandbox/venv/bin/python', PythonIdentity('CPython', 2, 7, 10), {('python', '2.7.10'): '/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/lib-dynload', ('setuptools', '33.1.1'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('wheel', '0.29.0'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('wsgiref', '0.1.2'): '/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7', ('pex', '1.4.3'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages', ('pip', '10.0.1'): '/Users/neutronbot/sandbox/venv/lib/python2.7/site-packages'}) -> [('cp27', 'cp27m', 'macosx_10_13_x86_64'), ('cp27', 'cp27m', 'macosx_10_13_intel'), ('cp27', 'cp27m', 'macosx_10_13_fat64'), ('cp27', 'cp27m', 'macosx_10_13_fat32'), ('cp27', 'cp27m', 'macosx_10_13_universal'), ('cp27', 'cp27m', 'macosx_10_12_x86_64'), ('cp27', 'cp27m', 'macosx_10_12_intel'), ('cp27', 'cp27m', 'macosx_10_12_fat64'), ('cp27', 'cp27m', 'macosx_10_12_fat32'), ('cp27', 'cp27m', 'macosx_10_12_universal'), ('cp27', 'cp27m', 'macosx_10_11_x86_64'), ('cp27', 'cp27m', 'macosx_10_11_intel'), ('cp27', 'cp27m', 'macosx_10_11_fat64'), ('cp27', 'cp27m', 'macosx_10_11_fat32'), ('cp27', 'cp27m', 'macosx_10_11_universal'), ('cp27', 'cp27m', 'macosx_10_10_x86_64'), ('cp27', 'cp27m', 'macosx_10_10_intel'), ('cp27', 'cp27m', 'macosx_10_10_fat64'), ('cp27', 'cp27m', 'macosx_10_10_fat32'), ('cp27', 'cp27m', 'macosx_10_10_universal'), ('cp27', 'cp27m', 'macosx_10_9_x86_64'), ('cp27', 'cp27m', 'macosx_10_9_intel'), ('cp27', 'cp27m', 'macosx_10_9_fat64'), ('cp27', 'cp27m', 'macosx_10_9_fat32'), ('cp27', 'cp27m', 'macosx_10_9_universal'), ('cp27', 'cp27m', 'macosx_10_8_x86_64'), ('cp27', 'cp27m', 'macosx_10_8_intel'), ('cp27', 'cp27m', 'macosx_10_8_fat64'), ('cp27', 'cp27m', 'macosx_10_8_fat32'), ('cp27', 'cp27m', 'macosx_10_8_universal'), ('cp27', 'cp27m', 'macosx_10_7_x86_64'), ('cp27', 'cp27m', 'macosx_10_7_intel'), ('cp27', 'cp27m', 'macosx_10_7_fat64'), ('cp27', 'cp27m', 'macosx_10_7_fat32'), ('cp27', 'cp27m', 'macosx_10_7_universal'), ('cp27', 'cp27m', 'macosx_10_6_x86_64'), ('cp27', 'cp27m', 'macosx_10_6_intel'), ('cp27', 'cp27m', 'macosx_10_6_fat64'), ('cp27', 'cp27m', 'macosx_10_6_fat32'), ('cp27', 'cp27m', 'macosx_10_6_universal'), ('cp27', 'cp27m', 'macosx_10_5_x86_64'), ('cp27', 'cp27m', 'macosx_10_5_intel'), ('cp27', 'cp27m', 'macosx_10_5_fat64'), ('cp27', 'cp27m', 'macosx_10_5_fat32'), ('cp27', 'cp27m', 'macosx_10_5_universal'), ('cp27', 'cp27m', 'macosx_10_4_x86_64'), ('cp27', 'cp27m', 'macosx_10_4_intel'), ('cp27', 'cp27m', 'macosx_10_4_fat64'), ('cp27', 'cp27m', 'macosx_10_4_fat32'), ('cp27', 'cp27m', 'macosx_10_4_universal'), ('cp27', 'cp27m', 'macosx_10_3_fat32'), ('cp27', 'cp27m', 'macosx_10_3_universal'), ('cp27', 'cp27m', 'macosx_10_2_fat32'), ('cp27', 'cp27m', 'macosx_10_2_universal'), ('cp27', 'cp27m', 'macosx_10_1_fat32'), ('cp27', 'cp27m', 'macosx_10_1_universal'), ('cp27', 'cp27m', 'macosx_10_0_fat32'), ('cp27', 'cp27m', 'macosx_10_0_universal'), ('cp27', 'none', 'macosx_10_13_x86_64'), ('cp27', 'none', 'macosx_10_13_intel'), ('cp27', 'none', 'macosx_10_13_fat64'), ('cp27', 'none', 'macosx_10_13_fat32'), ('cp27', 'none', 'macosx_10_13_universal'), ('cp27', 'none', 'macosx_10_12_x86_64'), ('cp27', 'none', 'macosx_10_12_intel'), ('cp27', 'none', 'macosx_10_12_fat64'), ('cp27', 'none', 'macosx_10_12_fat32'), ('cp27', 'none', 'macosx_10_12_universal'), ('cp27', 'none', 'macosx_10_11_x86_64'), ('cp27', 'none', 'macosx_10_11_intel'), ('cp27', 'none', 'macosx_10_11_fat64'), ('cp27', 'none', 'macosx_10_11_fat32'), ('cp27', 'none', 'macosx_10_11_universal'), ('cp27', 'none', 'macosx_10_10_x86_64'), ('cp27', 'none', 'macosx_10_10_intel'), ('cp27', 'none', 'macosx_10_10_fat64'), ('cp27', 'none', 'macosx_10_10_fat32'), ('cp27', 'none', 'macosx_10_10_universal'), ('cp27', 'none', 'macosx_10_9_x86_64'), ('cp27', 'none', 'macosx_10_9_intel'), ('cp27', 'none', 'macosx_10_9_fat64'), ('cp27', 'none', 'macosx_10_9_fat32'), ('cp27', 'none', 'macosx_10_9_universal'), ('cp27', 'none', 'macosx_10_8_x86_64'), ('cp27', 'none', 'macosx_10_8_intel'), ('cp27', 'none', 'macosx_10_8_fat64'), ('cp27', 'none', 'macosx_10_8_fat32'), ('cp27', 'none', 'macosx_10_8_universal'), ('cp27', 'none', 'macosx_10_7_x86_64'), ('cp27', 'none', 'macosx_10_7_intel'), ('cp27', 'none', 'macosx_10_7_fat64'), ('cp27', 'none', 'macosx_10_7_fat32'), ('cp27', 'none', 'macosx_10_7_universal'), ('cp27', 'none', 'macosx_10_6_x86_64'), ('cp27', 'none', 'macosx_10_6_intel'), ('cp27', 'none', 'macosx_10_6_fat64'), ('cp27', 'none', 'macosx_10_6_fat32'), ('cp27', 'none', 'macosx_10_6_universal'), ('cp27', 'none', 'macosx_10_5_x86_64'), ('cp27', 'none', 'macosx_10_5_intel'), ('cp27', 'none', 'macosx_10_5_fat64'), ('cp27', 'none', 'macosx_10_5_fat32'), ('cp27', 'none', 'macosx_10_5_universal'), ('cp27', 'none', 'macosx_10_4_x86_64'), ('cp27', 'none', 'macosx_10_4_intel'), ('cp27', 'none', 'macosx_10_4_fat64'), ('cp27', 'none', 'macosx_10_4_fat32'), ('cp27', 'none', 'macosx_10_4_universal'), ('cp27', 'none', 'macosx_10_3_fat32'), ('cp27', 'none', 'macosx_10_3_universal'), ('cp27', 'none', 'macosx_10_2_fat32'), ('cp27', 'none', 'macosx_10_2_universal'), ('cp27', 'none', 'macosx_10_1_fat32'), ('cp27', 'none', 'macosx_10_1_universal'), ('cp27', 'none', 'macosx_10_0_fat32'), ('cp27', 'none', 'macosx_10_0_universal'), ('py2', 'none', 'macosx_10_13_x86_64'), ('py2', 'none', 'macosx_10_13_intel'), ('py2', 'none', 'macosx_10_13_fat64'), ('py2', 'none', 'macosx_10_13_fat32'), ('py2', 'none', 'macosx_10_13_universal'), ('py2', 'none', 'macosx_10_12_x86_64'), ('py2', 'none', 'macosx_10_12_intel'), ('py2', 'none', 'macosx_10_12_fat64'), ('py2', 'none', 'macosx_10_12_fat32'), ('py2', 'none', 'macosx_10_12_universal'), ('py2', 'none', 'macosx_10_11_x86_64'), ('py2', 'none', 'macosx_10_11_intel'), ('py2', 'none', 'macosx_10_11_fat64'), ('py2', 'none', 'macosx_10_11_fat32'), ('py2', 'none', 'macosx_10_11_universal'), ('py2', 'none', 'macosx_10_10_x86_64'), ('py2', 'none', 'macosx_10_10_intel'), ('py2', 'none', 'macosx_10_10_fat64'), ('py2', 'none', 'macosx_10_10_fat32'), ('py2', 'none', 'macosx_10_10_universal'), ('py2', 'none', 'macosx_10_9_x86_64'), ('py2', 'none', 'macosx_10_9_intel'), ('py2', 'none', 'macosx_10_9_fat64'), ('py2', 'none', 'macosx_10_9_fat32'), ('py2', 'none', 'macosx_10_9_universal'), ('py2', 'none', 'macosx_10_8_x86_64'), ('py2', 'none', 'macosx_10_8_intel'), ('py2', 'none', 'macosx_10_8_fat64'), ('py2', 'none', 'macosx_10_8_fat32'), ('py2', 'none', 'macosx_10_8_universal'), ('py2', 'none', 'macosx_10_7_x86_64'), ('py2', 'none', 'macosx_10_7_intel'), ('py2', 'none', 'macosx_10_7_fat64'), ('py2', 'none', 'macosx_10_7_fat32'), ('py2', 'none', 'macosx_10_7_universal'), ('py2', 'none', 'macosx_10_6_x86_64'), ('py2', 'none', 'macosx_10_6_intel'), ('py2', 'none', 'macosx_10_6_fat64'), ('py2', 'none', 'macosx_10_6_fat32'), ('py2', 'none', 'macosx_10_6_universal'), ('py2', 'none', 'macosx_10_5_x86_64'), ('py2', 'none', 'macosx_10_5_intel'), ('py2', 'none', 'macosx_10_5_fat64'), ('py2', 'none', 'macosx_10_5_fat32'), ('py2', 'none', 'macosx_10_5_universal'), ('py2', 'none', 'macosx_10_4_x86_64'), ('py2', 'none', 'macosx_10_4_intel'), ('py2', 'none', 'macosx_10_4_fat64'), ('py2', 'none', 'macosx_10_4_fat32'), ('py2', 'none', 'macosx_10_4_universal'), ('py2', 'none', 'macosx_10_3_fat32'), ('py2', 'none', 'macosx_10_3_universal'), ('py2', 'none', 'macosx_10_2_fat32'), ('py2', 'none', 'macosx_10_2_universal'), ('py2', 'none', 'macosx_10_1_fat32'), ('py2', 'none', 'macosx_10_1_universal'), ('py2', 'none', 'macosx_10_0_fat32'), ('py2', 'none', 'macosx_10_0_universal'), ('cp27', 'none', 'any'), ('cp2', 'none', 'any'), ('py27', 'none', 'any'), ('py2', 'none', 'any')]
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10af78410>
pex: crawling link i=0 link=Link('file:///Users/neutronbot/.pex/build') follow_links=False
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/datadog/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0.tar.gz :: Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0.tarpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpH2I72y/datadog-0.21.0.tar.gz into distribution               pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpH2I72y/datadog-0.21.0.tar.gz into distribution :: Packaging dpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpH2I72y/datadog-0.21.0.tar.gz into distribution :: Packaging dpex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10c919910>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/decorator/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10c919910>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/requests/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10af78a90>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/simplejson/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/b0/e1/eab4fc3752e3d240468a8c0b284607899d2fbfb236a56b7377a329aa8d09/requests-2.18.4.tpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4.tar.gz                                                                  pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4.tar.gz :: Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4.tpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZHFL8B/requests-2.18.4.tar.gz into distribution              pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZHFL8B/requests-2.18.4.tar.gz into distribution :: Packaging pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZHFL8B/requests-2.18.4.tar.gz into distribution :: Packaging pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/8b/6c/c512c32124d1d2d67a32ff867bb3cdd5bfa6432660975f7ee753ed7ad886/simplejson-3.15.0pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0.tar.gz                                                                pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0.tar.gz :: Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZuBcG1/simplejson-3.15.0.tar.gz into distribution            pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZuBcG1/simplejson-3.15.0.tar.gz into distribution :: Packaginpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZuBcG1/simplejson-3.15.0.tar.gz into distribution :: Packaginpex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/6f/24/15a229626c775aae5806312f6bf1e2a73785be3402c0acdec5dbddd8c11e/decorator-4.3.0.tpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0.tar.gz                                                                  pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0.tar.gz :: Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0.tpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmptOCQHg/decorator-4.3.0.tar.gz into distribution              pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmptOCQHg/decorator-4.3.0.tar.gz into distribution :: Packaging pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmptOCQHg/decorator-4.3.0.tar.gz into distribution :: Packaging pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10cb46b90>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/chardet/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10cb46b90>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/idna/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10af78a90>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/urllib3/') follow_links=False
pex: Warning, using a UrllibContext which is known to be flaky.
pex: Please build pex with the requests module for more reliable downloads.
pex: Constructed UrllibContext context <pex.http.UrllibContext object at 0x10af5ba10>
pex: crawling link i=0 link=Link('https://pypi.python.org/simple/certifi/') follow_links=False
pex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/ee/11/7c59620aceedcc1ef65e156cc5ce5a24ef87be4107c2b74458464e437a5d/urllib3-1.22.tar.pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22.tar.gz                                                                     pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpc82NEY/urllib3-1.22.tar.gz into distribution :: Packaging urlpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpc82NEY/urllib3-1.22.tar.gz into distribution :: Packaging urlpex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/fc/bb/a5768c230f9ddb03acc9ef3f0d4a3cf93462473795d18e9535498c8f929d/chardet-3.0.4.tarpex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4.tar.gz                                                                    pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4.tar.gz :: Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4.tar.gpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpVfrIXN/chardet-3.0.4.tar.gz into distribution                pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpVfrIXN/chardet-3.0.4.tar.gz into distribution :: Packaging chpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpVfrIXN/chardet-3.0.4.tar.gz into distribution :: Packaging chpex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/4d/9c/46e950a6f4d6b4be571ddcae21e7bc846fcbb88f1de3eff0f6dd0a6be55d/certifi-2018.4.16pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16.tar.gz                                                                pex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16.tar.gz :: Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpDYnG9e/certifi-2018.4.16.tar.gz into distribution            pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpDYnG9e/certifi-2018.4.16.tar.gz into distribution :: Packaginpex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpDYnG9e/certifi-2018.4.16.tar.gz into distribution :: Packaginpex: Building pex :: Resolving distributions :: Fetching https://files.pythonhosted.org/packages/f4/bd/0467d62790828c23c47fc1dfa1b1f052b24efdf5290f071c7a91d0d82fd3/idna-2.6.tar.gz#spex: Building pex :: Resolving distributions :: Fetching file:///Users/neutronbot/.pex/build/idna-2.6.tar.gz                                                                         pex: Building pex :: Resolving distributions :: Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp1o_Tym/idna-2.6.tar.gz into distribution :: Packaging idna ::  datadog 0.21.0/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpnkCldF
  simplejson 3.15.0
  urllib3 1.22
  chardet 3.0.4
  requests 2.18.4
  certifi 2018.4.16
  idna 2.6
  decorator 4.3.0
pex: Building pex: 7081.6ms
pex:   Resolving interpreters: 0.8ms
pex:     Setting up interpreter /Users/neutronbot/sandbox/venv/bin/python: 0.8ms
pex:   Resolving distributions: 7076.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0.tar.gz: 7.3ms
pex:       Fetching file:///Users/neutronbot/.pex/build/datadog-0.21.0.tar.gz: 6.7ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpH2I72y/datadog-0.21.0.tar.gz into distribution: 515.2ms
pex:       Packaging datadog: 468.7ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpPDrnb_: 464.8ms
pex:     Fetching https://files.pythonhosted.org/packages/b0/e1/eab4fc3752e3d240468a8c0b284607899d2fbfb236a56b7377a329aa8d09/requests-2.18.4.tar.gz#sha256=9c443e7324ba5b85070c4a818ade28bfabedf16ea10206da1132edaa6dda237e: 52.5ms
pex:     Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4.tar.gz: 2.0ms
pex:       Fetching file:///Users/neutronbot/.pex/build/requests-2.18.4.tar.gz: 1.4ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZHFL8B/requests-2.18.4.tar.gz into distribution: 425.5ms
pex:       Packaging requests: 393.7ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpenSi5f: 391.1ms
pex:     Fetching https://files.pythonhosted.org/packages/8b/6c/c512c32124d1d2d67a32ff867bb3cdd5bfa6432660975f7ee753ed7ad886/simplejson-3.15.0.tar.gz#sha256=ad332f65d9551ceffc132d0a683f4ffd12e4bc7538681100190d577ced3473fb: 42.2ms
pex:     Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0.tar.gz: 1.9ms
pex:       Fetching file:///Users/neutronbot/.pex/build/simplejson-3.15.0.tar.gz: 1.3ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpZuBcG1/simplejson-3.15.0.tar.gz into distribution: 1800.4ms
pex:       Packaging simplejson: 1761.5ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp504cb_: 1758.0ms
pex:     Fetching https://files.pythonhosted.org/packages/6f/24/15a229626c775aae5806312f6bf1e2a73785be3402c0acdec5dbddd8c11e/decorator-4.3.0.tar.gz#sha256=c39efa13fbdeb4506c476c9b3babf6a718da943dab7811c206005a4a956c080c: 39.7ms
pex:     Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0.tar.gz: 1.8ms
pex:       Fetching file:///Users/neutronbot/.pex/build/decorator-4.3.0.tar.gz: 1.2ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmptOCQHg/decorator-4.3.0.tar.gz into distribution: 335.0ms
pex:       Packaging decorator: 320.3ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpptmVtK: 318.1ms
pex:     Fetching https://files.pythonhosted.org/packages/ee/11/7c59620aceedcc1ef65e156cc5ce5a24ef87be4107c2b74458464e437a5d/urllib3-1.22.tar.gz#sha256=cc44da8e1145637334317feebd728bd869a35285b93cbb4cca2577da7e62db4f: 50.3ms
pex:     Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22.tar.gz: 2.2ms
pex:       Fetching file:///Users/neutronbot/.pex/build/urllib3-1.22.tar.gz: 1.6ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpc82NEY/urllib3-1.22.tar.gz into distribution: 548.3ms
pex:       Packaging urllib3: 467.6ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpcZgyTI: 464.3ms
pex:     Fetching https://files.pythonhosted.org/packages/fc/bb/a5768c230f9ddb03acc9ef3f0d4a3cf93462473795d18e9535498c8f929d/chardet-3.0.4.tar.gz#sha256=84ab92ed1c4d4f16916e05906b6b75a6c0fb5db821cc65e70cbd64a3e2a5eaae: 154.6ms
pex:     Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4.tar.gz: 4.4ms
pex:       Fetching file:///Users/neutronbot/.pex/build/chardet-3.0.4.tar.gz: 3.7ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpVfrIXN/chardet-3.0.4.tar.gz into distribution: 968.7ms
pex:       Packaging chardet: 675.9ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpegrA7s: 672.3ms
pex:     Fetching https://files.pythonhosted.org/packages/4d/9c/46e950a6f4d6b4be571ddcae21e7bc846fcbb88f1de3eff0f6dd0a6be55d/certifi-2018.4.16.tar.gz#sha256=13e698f54293db9f89122b0581843a782ad0934a4fe0172d2a980ba77fc61bb7: 45.1ms
pex:     Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16.tar.gz: 2.2ms
pex:       Fetching file:///Users/neutronbot/.pex/build/certifi-2018.4.16.tar.gz: 1.5ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpDYnG9e/certifi-2018.4.16.tar.gz into distribution: 341.4ms
pex:       Packaging certifi: 328.1ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpJJndbz: 325.7ms
pex:     Fetching https://files.pythonhosted.org/packages/f4/bd/0467d62790828c23c47fc1dfa1b1f052b24efdf5290f071c7a91d0d82fd3/idna-2.6.tar.gz#sha256=2c6a5de3089009e3da7c5dde64a141dbc8551d5b7f6cf4ed7c2568d0cc520a8f: 44.3ms
pex:     Fetching file:///Users/neutronbot/.pex/build/idna-2.6.tar.gz: 1.4ms
pex:       Fetching file:///Users/neutronbot/.pex/build/idna-2.6.tar.gz: 0.8ms
pex:     Translating /private/var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmp1o_Tym/idna-2.6.tar.gz into distribution: 466.5ms
pex:       Packaging idna: 445.4ms
pex:         Installing /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpnkCldF: 443.0ms
Running PEX file at /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpNqI2DQ with args []
pex: PEX.run invoking /Users/neutronbot/sandbox/venv/bin/python /var/folders/qy/0j8_7hqx47b561h6r6z0dcs80000gp/T/tmpNqI2DQ
Python 2.7.10 (default, Oct  6 2017, 22:29:07)
[GCC 4.2.1 Compatible Apple LLVM 9.0.0 (clang-900.0.31)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>>

Wanted to note here - I was able to resolve the issues @premal was seeing for our users by installing python 2.7.13+ via brew (system python was 2.7.10) and resetting their venvs.

"resetting their venvs" definitely screams "setuptools version" to me, fwiw.

authors: DrumMachineLearning georgeliaw jsirois kmannislands kwlzn premal

repo: pantsbuild/pex