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Starring in this epic drama set in the high stakes world of espionage, Matt Damon plays Edward Wilson, an exceptionally bright and talented son of privilege who is recruited from the campus of Yale University to join the Office of Strategic Services, the precursor to the CIA, at the beginning of World War II. Wilson's acute mind, spotless reputation and sincere belief in American values render him a prime candidate for a career in intelligence, as do his deeply embedded commitment to honor and quite secretive nature. As Wilson becomes a veteran operative in counter-intelligence during the Cold War, not even his wife Clover, played by Angelina Jolie, nor his beloved son Edward Jr., can divert him from a path that will force him to sacrifice everything in service to his country.
"The Departed" is set in South Boston, where the state police force is waging war on organized crime. Young undercover cop Billy Costigan (Leonardo DiCaprio) is assigned to infiltrate the mob syndicate run by gangland chief Costello (Jack Nicholson). While Billy is quickly gaining Costello's confidence, Colin Sullivan (Matt Damon), a hardened young criminal who has infiltrated the police department as an informer for the syndicate, is rising to a position of power in the Special Investigation Unit. Each man becomes deeply consumed by his double life, gathering information about the plans and counter-plans of the operations he has penetrated. But when it becomes clear to both the gangsters and the police that there's a mole in their midst, Billy and Colin are suddenly in danger of being caught and exposed to the enemy—and each must race to uncover the identity of the other man in time to save himself.