The teaching math through comedy link is too cool (and unfortuantely a bit too far from me). I am all for detaching math from notions of solemnity - and am working towards making PyGeo at least a bit sillier. Why limit representing a point in space to, say, a sphere. Why not - I dont' know - a propeller blade. Nothing is accomplished in particular except some silliness - which is something.
On the pygame front - I had the opportunity to meet with Winston Wolff who is working in New York on a business model centered around teaching game programming as supplementary education, mostly for gifted children. He is a CS guy out of UC Berkeley who has some background in the game industry.
I was trying to sell him PyGeo(sell as in free but I'd love to see it used in your curriculum), so I did more talking than listening.
But he certainly seems to be smart, with the right background, and committed to his ideas, both as ideas and as a way to pay the bills.