The many faces of Sean Penn

“Carlito’s Way” (1993)

Penn the Slimy Lawyer: Just when Carlito (Al Pacino) thought he was home free, his crooked friends drag him back in. Sean Penn plays the crookedest of them all—a smarmy lawyer who smirks as he gets Carlito out of a 30-year prison sentence only five years in. Almost unrecognizable as a balding, curly-red-haired attorney, Penn plays a criminal who’s losing the battle against his cocaine-addled ego, and Pacino is the one-time crook trying to go straight ultimately undone by his choice of friends.