The Departed (2006)

South Boston cop Billy Costigan (Leonardo DiCaprio) goes undercover to infiltrate the organization of gangland chief Frank Costello (Jack Nicholson). As Billy gains the mobster's trust, a career criminal named Colin Sullivan (Matt Damon) infiltrates the police department and reports its activities to his syndicate bosses. When both organizations learn they have a mole in their midst, Billy and Colin must figure out each other's identities to save their own lives.