Jesse Brown, a BoingBoing guest-blogger, is the host of TVO's Search Engine podcast.
The most creative guy I knew in high school was this kid Ba Blackstock. He drew hilarious cartoons, directed theatrical adaptations of Dan Clowes comics and made crazy short movies.
Later, he spent years of his life making this cartoon. He went old-school, penciling by hand over a light board (he's entirely self-taught). Then he inked and colored it and added 3D stuff digitally. Of course, he nearly lost his mind in the process.
The resulting cartoon speaks for itself.
NOTE: this is just one chapter. I recommend watching the whole 14 minute thing (link.)