16. Earl Grayce, Kalifornia (1993)
Played By: Brad Pitt
Vocational irony is one our least favorite devices in entertainment. How often have we seen, "He's a doctor, but he can't fix himself," or "He's a powerful ruler, but he can't hold court over his own family" premises? Kalifornia marks one of the most ridiculous examples of this we've ever seen.
The premise: A couple sets out to study serial killers, only to run afoul of a serial killer. Brad Pitt has the unenviable task of manifesting that irony into being via Earl Grayce, the hillbilly psychopath. Pitt gives it a damn good shot: Earl has a free-wheeling dynamic quality that transcends your run-of-the-mill redneck stereotypes.