Cast: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, Anthony Anderson, Alec Badwin
Oscar Wins: Best Picture, Best Director (Martin Scorsese), Best Film Editing (Thelma Schoonmaker)
Oscar Nominations: Best Writing, Adapted Screenplay (William Monahan), Best Supporting Actor (Mark Wahlberg)
SUMMARY: Francis “Frank” Costello (Jack Nicholson) is the well-known head of the Irish mob in South Boston, and has held this position for many years. While collecting money from a store one day, he meets pre-teen Colin Sullivan (Matt Damon), and takes him under his wing. Sullivan grows up in the world of organized crime, but as an adult, he enters the police academy. Sullivan’s star rises quickly, until he is a high-ranking officer in the Special Investigations Unit, which is focusing on organized crime – particularly Frank Costello. Unbeknownst to virtually everyone around him, Sullivan is still working for Costello, acting as a mole inside the state police. Billy Costigan (Leonardo DiCaprio) enters the police academy at the same time as Sullivan, but has much less success. Before graduation, he meets with Captain Queenan (Martin Sheen) and Staff Sergeant Dignam (Mark Wahlberg), who ask him to become a spy inside Costello’s organization. Costigan is perfect for the role because he has many family members with mob ties; told that this is virtually the only way he can become a police officer, Costigan agrees to drop out of the academy and serve a prison sentence to create a reputation. Costigan is eventually accepted into Costello’s organization, and becomes a trusted (if somewhat volatile) associate. Meanwhile, Sullivan continues to tip Costello off about police activities. He also meets Madolyn Madden (Vera Farmiga), a psychiatrist who frequently works with police officers. A relationship quickly develops, but she has no idea of his connections to Costello. Coincidentally, the terms of Costigan’s parole dictate that he also see Madolyn regularly. After the first visit, Costigan is transferred to a different psychiatrist, but continues to see Madolyn on a social basis. Though they both have feelings for the other, Madolyn refuses to act on them, instead developing a friendly, honest relationship with Costigan. Though both men experience great success in their deceptions for a time, both the police department and the mob begin to suspect they have a mole in their organization. Sullivan is tasked both with both finding the informer within the police and helping Costello investigate his men.
When asked for his personal information, Costigan starts to get worried. He provides false information on a specially marked envelope, then follows Costello after he retrieves the packet. He follows him to a theater where Costello meets with Sullivan; after Sullivan leaves, Costigan pursues him. In the process of trying to get away, Sullivan stabs a man to death; he does escape, but neither man is able to concretely identify the other. With no other way to find the mole, Sullivan assigns a tail to Queenan, using the excuse that he believes Queenan to be the mole. Queenan does arrange to meet Costigan at an abandoned building, and is followed by fellow officers. When Sullivan learns that Queenan is meeting with the mole, he alerts Costello to the location of the meeting. Meanwhile, Costigan and Queenan have realized that Queenan was followed. Costigan escapes to protect himself, while Queenan stays behind to head off anybody who attempts to pursue. Costello’s men enter the building (seen by the police tail), and throw Queenan off the roof. He lands right in front of the escaping Costigan, who tells the other mobsters that he has just arrived to help them. A gunfight erupts between the police and the mobsters, and several on each side are wounded or killed. Later that evening, it is revealed that one of the slain mobsters, Delahunt, was an undercover police officer. One of the wounded mobsters puts together that Costigan is also a mole, but dies before revealing anything. Back at police headquarters, Sullivan announces that he will take charge of undercover operations; an incensed Dignam (the only one besides Queenan who knows about Costigan) resigns, rather than work with him. It is also clear that Dignam is suspicious of Sullivan. With access to Queenan’s files, Sullivan manages to call Costigan, but fails to learn anything that will lead to an identification. He also learns that Costello is an informant for the FBI, which creates apprehension about his own safety and future career. When Costello arranges a big drug deal, Costigan tips off the police, but Sullivan alerts Costello enough to protect him. Consequently, the drug deal turns into a mess, and a shootout erupts between the mobsters and the police, who have arrived to raid the proceedings. Sullivan manages to find Costello in the melee, who admits that he is working with the FBI; Sullivan ends up shooting him multiple times, which is perceived as a heroic act by the other policemen. With his mission over, Costigan finally reveals himself as the mole, and enters Sullivan’s office. However, he notices the envelope with his personal information (that Costello had requested) on Sullivan’s desk, and puts the pieces together: he leaves immediately. Sullivan also realizes what has happened, and deletes Costigan’s police file so that he will have no record of being an officer.
After he flees, Sullivan is unable to find Costigan, but continues life and work as normal. One day, he receives a letter from Costigan that Madolyn intercepts: when she opens it, she finds an audio recording that reveals Sullivan to be the mole in the police force. When he talks to Costigan on the phone, Sullivan learns that virtually all of his conversations with Costello had been recorded – and that Costigan is in possession of the tapes. Costigan requests a meeting with Sullivan on the roof of the building Queenan was thrown off. When Sullivan arrives, Costigan arrests him; another police officer then arrives to help. The officer is unsure of what is going on, but only holds the men at gunpoint: Costigan had also requested that Dignam come, but the man is nowhere in sight. Costigan takes Sullivan down in the elevator at gunpoint; when the doors open on the ground floor, Costigan is immediately shot. The assassin is yet another police officer, Barrigan, who reveals to Sullivan that he is also one of Costello’s moles. When the first police officer comes down in the elevator, he is shot; Sullivan then shoots Barrigan before leaving the building. At headquarters, he passes the story that Barrigan was the mole, and had killed the heroic Costigan before also being killed (by Sullivan). Sullivan and Madolyn both go to Costigan’s funeral, but their relationship is over: Madolyn refuses to even speak to Sullivan. Sullivan returns to his apartment, only to find Dignam waiting for him: Dignam shoots Sullivan, then walks out.
MY TAKE: Having seen so many movies, it’s hard to shock or surprise me: I anticipate most twists, and the most famous ones in movie history (Darth is Luke’s father, Bruce Willis is dead in The Sixth Sense, Norman Bates dresses up like his mother) happened either before I was born or when I was a kid. They have become so well known that they are no longer surprising to someone watching them for the first time. However, I will have to say that I did not anticipate the ending of this movie. Since it is a Martin Scorsese movie, I did not expect it to have a happy ending, but I was completely unprepared for Costigan to get shot as soon as the elevator opens. I didn’t anticipate any of the murders that happen directly after his, either, but his was definitely the most shocking. It’s so abrupt, and happens so quickly that I was literally left saying, “What the hell just happened?” Although the ending is typically bloody and violent, the rest of the movie really isn’t: it’s more of a psychological thriller, as Costigan and Sullivan race to identify each other first. It’s a really interesting duality. Sullivan appears to be the good guy, and he even looks more upstanding that Costigan. Even though Costigan has a long family history with the mob, he is the one who stays true and committed to the police, while Sullivan falls deeper and deeper into criminal activity. It’s incredibly frustrating to watch him receive more resources and power that he uses to help Costello, and I wondered how in the world Costigan was ever going to prove the truth. In this aspect, the ending was kind of a disappointment: I would have liked to see Sullivan publicly revealed to be the mole, rather than just being offed by Dignam. Still, it’s a really tense, thrilling movie.