18. Tom Cruise as Les Grossman in Tropic Thunder (2008)
Notable Jewish Moment: If it's not the fact that his name is "Les Grossman," it's that he's powerful, works in Hollywood, is balding, fat, has a hairy chest covered with a gold chain, and can usually be found screaming at subordinates, in a send-up of every cliche about Hollywood Jews. Still not convinced? His painfully rhythm-deficient victory dance to Ludacris' "Get Back" at the end of the film seals it up.
Classic Quote: "Look, fuckstick, I'm incredibly busy so why don't you get the hell out of here before I snap your dick off and jam it into your ass?"
A megalomaniacal, sociopathic 21st century Jewish man in Hollywood? Never, except, always. Tom Cruise's "cameo" in director/star Ben Stiller's epic jungle war comedy tops off an already incredible cast, but even more remarkable is the fact that Stiller managed to produce one of the rare instances where Cruise ever has or will ever play against self-seriousness and appearance.
In Tropic Thunder, he donned a fat suit and a bald headcap to play relentless studio mogul Les Grossman, who—assistant abuse, obesity, demanding psychosis and all—was supposedly inspired by Stiller's producing partner Stuart Cornfeld (with sprinkles of uber-producer Scott Rudin, too). While the role of Hollywood Jew is a tired-and-true one, in this case, there's never been (or likely will be) a more unlikely portrayal.