The Departed is a 2006 American crime film, a remake of the 2002 Hong Kong film Infernal Affairs. The film was directed by Martin Scorsese, written by William Monahan, and stars Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga and Alec Baldwin. It won four Academy Awards at the 79th Academy Awards, including Best Picture, and an Academy Award for Best Director win for Scorsese.
This film takes place in Boston, Massachusetts, where Irish Mob boss Francis "Frank" Costello (Nicholson) plants Colin Sullivan (Damon) as an informant within the Massachusetts State Police. Simultaneously, the police assign undercover cop Billy Costigan (DiCaprio) to infiltrate Costello's crew. When both sides realize the situation, each man attempts to discover the other's true identity before being found out.
At a young age, Colin Sullivan (Damon) is introduced to organized crime through Irish mobster Frank Costello (Nicholson) who grooms him along with other youths in the Irish neighborhood of Southie, a district in northern Boston. Turning into a father figure to Sullivan, Costello trains him to become his mole inside the Massachusetts State Police. Performing exceptionally while helping Costello remove his underworld enemies, Sullivan is accepted into the Special Investigation Unit (SIU), which focuses on organized crime. Before he graduates from the Police Academy, Billy Costigan (DiCaprio) is asked by Captain Queenan (Sheen) and the abusive Staff Sergeant Dignam (Wahlberg) to become an undercover agent, as his childhood spent wandering between two Boston neighborhoods and his family ties to organized crime make him a perfect infiltrator. He agrees to drop out of the academy and does time in prison on a fake assault charge to increase his credibility as a criminal.
As both men infiltrate their respective organizations, Sullivan begins a romance with psychiatrist Madolyn Madden (Farmiga). Costigan sees Madolyn as part of his probation and also develops a relationship with her. Later on Sullivan is unable to make love to Madolyn because of his impotence. Shortly after, Costigan makes love with Madolyn at her apartment before she moves in with Sullivan. After Costello barely escapes a sting operation, both moles become aware of the other's existence (though not his identity). Sullivan is assigned to find the "rat" in SIU and asks Costello for his crew's personal information to allow him to determine who is the informer within Costello's crew. Costigan follows Costello into a movie theater where Costello gives Sullivan an envelope with the details of his crew. Costigan then chases Sullivan through Boston's Chinatown, during which Sullivan stabs an innocent bystander. When it is all over, both men still do not know each other's true identity. Sullivan then has Queenan tailed as he meets Costigan in an abandoned building. Costello sends his men in and Queenan distracts them to let Costigan escape. He is thrown from the roof and dies at the feet of Costigan. When the mobsters escape, Costigan pretends he has come to rejoin them. The trailing state troopers open fire on Costello's crew, which causes casualties on both sides. Later, at one of Costello's safe houses, Delahunt (one of Costello's enforcers) reveals to Costigan that he is aware of his true identity just before he dies from his gunshot wounds.
His actions now under scrutiny, Sullivan is attacked by a suspicious Dignam because of Queenan's death. Dignam is subsequently placed on administrative leave. Using Queenan's bloodstained phone, Sullivan reaches Costigan, who refuses to abort his mission. Sullivan learns of Costello's role as an informant for the FBI from Queenan's diary, causing him to worry about his double identity being revealed. With Costigan's help, Costello is tracked to a cocaine drop-off, where he and his crew become trapped in a gunfight with police, resulting in most of the mobsters being killed. As the wounded Costello attempts an escape he is confronted by Sullivan. Costello admits he is an occasional FBI mole and tries to shoot Sullivan. Sullivan fires first, killing Costello. With Costello dead, Sullivan is applauded for his actions. In good faith, Costigan comes to him for restoration of his true identity. Costigan also notices the envelope containing the details of Costello's men on Sullivan's desk and flees from the building. Knowing he has been found out, Sullivan erases all records of Costigan as a trooper from the police agency's computer system.
Costigan leaves an envelope in the care of Madolyn. Some time later, Madolyn reveals to Sullivan that she is pregnant with his child, when it is in fact Costigan's. After telling Sullivan, Madolyn discovers a small package from Costigan in the mail. The package contains an audio CD and a phone number for Sullivan to contact him with. Madolyn listens to the CD and discovers that it contains audio recordings of Costello's conversations with Sullivan. Sullivan walks in on her and tries to assuage her suspicions, but she locks herself in a room and refuses to hear any more from him. Losing composure, Sullivan hastily contacts Costigan, who reveals that Costello recorded every conversation he had with Sullivan. Since Costigan was the only person Costello actually trusted, Costello's attorney left Costigan in possession of the recordings and therefore Costigan intends to implicate Sullivan at last. In order to reach a settlement, they agree to meet at the empty building where Queenan died.
On the roof of the building, Costigan catches Sullivan off-guard and hand-cuffs him at gunpoint with intent to arrest him. As Costigan had secretly arranged, Officer Brown appears on the roof as well. Shocked and disturbed by the scene, Brown draws his gun on Costigan. Costigan attempts to justify his actions by exposing Sullivan as the rat, but Brown does not fully believe him and continues to hold them at gunpoint. Costigan asks Brown why Dignam did not accompany him as per their agreement, but Brown does not give an answer. Using Sullivan as a shield, Costigan leads Sullivan into an elevator. As it reaches the ground floor and the door opens, Costigan is shot and killed by Barrigan, another police officer. Brown reaches the ground floor and is shot and killed as well. Barrigan reveals to Sullivan that Costello had more than one mole in the police department, and suggests that the two of them must go on the lam to avoid being traded to the FBI. Sullivan tricks Barrigan into handing him a gun and then shoots him in the back of the head, leaving Sullivan the only survivor of the meeting. At police headquarters, Sullivan blames all mole activity on Barrigan and has Costigan posthumously rewarded with the Medal of Merit.
At Costigan's funeral, Sullivan and Madolyn stand on opposite sides of Costigan's grave. Sullivan observes Madolyn throughout the service; she is clearly distraught at Costigan's death. Sullivan waits after the service to attempt reconcile with Madolyn and discuss the future of her child. She walks past him without a word. Some time later, Sullivan is about to enter his apartment with a bag of groceries. He opens the door to find Dignam waiting for him, wearing hospital footies over his shoes and surgical gloves to leave no trace of his presence. Aware of Sullivan's treachery and escape from punishment, Dignam aims a pistol at Sullivan's head. Sullivan only manages to splutter "Okay..." before Dignam shoots him in the head. As Sullivan collapses to the floor, Dignam calmly exits the apartment. The camera pans up from Sullivan's body to reveal a rat crawling along the railing of his apartment's balcony, with the view of the Massachusetts State House in the background.
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