Sean Penn plays Carlito's close friend and attorney, David Kleinfeld. Penn is hardly recognizable with a balding, curly red hair and glasses. This is one of Penn's best performances and he earned a Golden Globe nomination for best actor.Penn first gained fame in his early hit roles in Bad Boys and Fast Times at Ridgemeont High. His character in Fast Times, Spicoli, was in my opinion his best acting. He finds himself often cast as an anti-authorithan and trouble making character.
His latest film released was U Turn. Other recent films include She's So Lovely, The Game, and Dead Man Walking.