2. SEAN PENN AS DAVID KLEINFELD IN CARLITO'S WAY (1993)

The epitome of sleaze, this urchin of a mob lawyer dreams of being a respected bad guy and steals one million bucks from an imprisoned boss instead of delivering the payoff to spring his client. When forced to help the mobster escape from the Rikers Island prison barge, Kleinfeld kills him and his son. All shady shit, to be sure, but the capper comes when he tries to wriggle his way out of legal problems by offering to testify against his "friend" and former hood Carlito Brigante for crimes that he hasn't actually committed. Apparently you can't trust a lawyer as far as you can throw them—unless you're throwing them in a river.