2. Billy Crystal in Deconstructing Harry
Its somewhat surprising that Woody Allen and Billy Crystal had not worked together before this film. They were two of the most successful Jewish comedians in the history of show business so it seemed only natural that they would collaborate at some point. Woody cast Crystal in the small but essential dual role of the main characters best friend and the Devil. Crystal plays the latter part as a laid-back CEO of Hell. Its certainly one of the more unconventional portrayals of Satan as he and Woody bond over their strikingly similar sex lives. You have to wonder who Woody would cast as God given that hes an avowed atheist. Why not Mel Brooks? http://www.youtube.com/watch?v=HKGjqeb16R8