The Departed (2006)

An undercover Boston cop (Oscar-winner Leonardo DiCaprio) and a mole (Oscar-winner Matt Damon) in the police attempt to identify each other while infiltrating the Irish Mob in South Boston. The head of that Irish gang is Frank Costello played by three-time Oscar-winner Jack Nicholson and the main handlers for the undercover cop are played by Oscar-nominee (for this film) Mark Wahlberg and Emmy-winner Martin Sheen. Things just get increasingly complicated as investigations on both ...