Best: The Joker (Batman)

Portrayed by: Jack Nicholson 

The Joker's favored colors, green and purple, technically should not work on anyone. Yet time and again he gets his color blocking on and looks awesome. Without a doubt, the flyest incarnation was Jack Nicholson's scene-stealing turn in Tim Burton's Batman. The fact that he wrought mayhem while rocking out to Prince just made it even better.