Ronald Oussoren added the comment:

You could trace using dtruss (as root), which behaves similarly to strace.

What happens when you first set "http_proxy" in the environment:

$ env http_proxy= python -m SimpleHTTPServer

If that doesn't cause problems the hang is caused by the _scproxy extension, 
which urllib uses to get the system proxy settings on OSX.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue21035>
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