I'm using PIL to draw lots of polygons consisting of big number of points (from couple hundred to couple thousands). With Cpython all polygons were processed 3 times faster than PyPy. Just to give an example... One polygon consisting of 352 points:
PyPy - 0.00620603561401
Cpython - 0.000882148742676
start = time()
draw.polygon(pixels, outline='rgb(255, 255, 255)', fill='rgb(0, 0, 0)')
print time()-start
I'm using Python 2.7.3 and PyPy 1.9 on Ubuntu 12.10 module - Pillow 1.7.8