Edit: The secret to fixing this lies in Universal Binaries in Macports!
Getting the Python Imaging Library working with both Python2.5 and Python2.6 on Snow Leopard proved tricky. Using MacPorts, it’s pretty easy to install PIL for Python2.6. After installing MacPorts, run the following:
sudo port install freetype jpeg tiff libpng
Once these libraries are installed, Grab the latest version of PIL and run:
sudo /usr/bin/python2.6 setup.py build install
The tricky part is getting PIL to work under Python 2.5. After a good amount of time searching for the right way to build PIL, I found a post that suggested grabbing the python.org binary version. So, I cheated and did just that.
After downloading the dmg, show the package contents for PIL-1.1.6-py2.5-macosx10.4.mpkg.
Then navigate to Contents -> Packages -> PIL-platlib-1.1.6-py2.5-macosx10.4.pkg and show its package contents.
In there you will find Archive.pax.gz. Double clicking on that file will extract the contents to an Archive directory.
Finally, copy PIL and PIL.pth over:
> cd /Library/Python/2.5/site-packages/
> sudo cp -rp ~/Downloads/Archive/PIL .
> sudo cp -rp ~/Downloads/Archive/PIL.pth .
At this point, PIL should work for both Python2.5 and Python2.6