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The following FAQ entries may contain spoilers. Only the biggest ones (if any) will be covered with spoiler tags. Spoiler tags are used sparingly in order to make the page more readable.
For detailed information about the amounts and types of (a) sex and nudity, (b) violence and gore, (c) profanity, (d) alcohol, drugs, and smoking, and (e) frightening and intense scenes in this movie, consult the IMDb Parents Guide for this movie. The Parents Guide for The Departed can be found here.
Two aspiring Massachusetts police officers, Colin Sullivan (Matt Damon) and William 'Billy' Costigan (Leonardo DiCaprio), are assigned to the Special Intelligence Unit (SIU). South Boston-raised Colin is immediately assigned to a cushy elite unit. Also a South Bostie whose family had multiple ties to crime, Billy is assigned to the undercover unit. Both become involved with criminal Irish mob boss Frank Costello (Jack Nicholson).
The Departed is a remake of Mou gaan dou (Infernal Affairs), a 2002 Hong Kong movie written by Chinese screenwriters Felix Chong and co-director Alan Mak. Chong and Mak's screenplay was adapted for The Departed by American screenwriter William Monahan. The movie won the 2007 Academy Award for Best Motion Picture.
The Departed, and the character of Frank Costello, is loosely based on the story of Whitey Bulger [born 1929], a Boston Southie considered by Law Enforcement to be one of the last Irish mobsters. Bulger often gave information to John Connolly, an FBI agent, on the Italian Mafia in Boston, in order to take over the city himself. Bulger spent his career as a psychotic killer and even ran guns for the IRA in the 1970s. Even after Bulger stopped passing on actual information to the FBI, Connolly still protected him from the Staties. Bulger was captured in Santa Monica, CA in 2011 after being on the run for over 15 years and is currently awaiting trial after pleading not guilty to nearly 50 criminal charges.
It looks like the cover to the September 1989 issue: Wolverine Vol. 1 Issue #11. "The Gehenna Stone Affair: Pt. 1 of 6" : Brother's Keeper. Writer: Peter David, Penciler: John Buscema.
When Colin says that he's a State Police Detective, the Realtor asks if he is married. Colin says no, at which point the Realtor says "Because this is kind of a large apartment". Not only is the apartment large for one person, but the realtor is likely wondering how a young cop on a single income can afford the rent alone. Colin informs him he has a co-signer, but we also know that Colin would also be receiving money for working for Frank Costello (although obviously he can't declare this income to the realtor).
This is not stated in the film. When Billy asks, Frank tells him that "Mr. French" (Ray Winstone) is an alias. In one scene, however, Frank calls Mr. French "Arnold" a few times, so it's possible that Arnold is Mr. French's first name.
Costello arranged to sell the computer chips to the Chinese, but likely had no intention of actually delivering the real chips (Queenan (Martin Sheen) observes that we may be at war with the Chinese in the future and Costello's selling them military hardware). Frank was an FBI informant, so he tipped the FBI where to apprehend them, therefore Frank keeps the money and the Chinese get arrested. Win-win for Frank.
Colin and Frank frame a man named Jimmy Pappas for the hit to cover up the fact that Frank ordered both men to be murdered in order to save Billy from execution after he severely beat two of the Italian gangsters in a store. It's never revealed who really killed the two men, but it would be safe to assume that it was Mr. French, along with either Fitzy or Delahunt.
Billy is sent a series of tapes that Frank secretly recorded of his conversations with Colin, and Billy sends a copy to Colin. Madolyn (Vera Farmiga) intercepts it, listens to it, and realizes that Colin was working with Frank. Colin meets Billy to try to pay him off, but Billy arrests him. Billy has called Brown (Anthony Anderson), his friend from the academy, to help him, and Brown allows him to take Colin down the elevator. When the elevator opens, Colin's academy friend Barrigan (James Badge Dale) shoots Billy, killing him. When Brown gets downstairs and sees what's happened, Barrigan shoots him as well, and then reveals to Colin that he also worked for Costello ("Did you think you were the only one?"). Colin then shoots Barrigan. He tells the police that Barrigan was Frank Costello's mole and recommends Costigan to be honored by the department. At the funeral, he asks a crying Madolyn about the baby, but she walks right past him. When Colin returns to his apartment, he finds Dignam (Mark Wahlberg) waiting for him, Dignam has become aware that Colin was Frank's primary mole, due to the information given to Madolyn by Billy near the end. Dignam kills Colin. In the final scene, a rat runs along the outside balcony railing, framed by the gold dome of the Massachusetts State House in the background.
Costello's opening narration - "Gimme Shelter" by The Rolling Stones.Costigan and Sullivan go through the police academy - "Cops and Criminals" by Howard Shore featuring Marc Ribot (dobro) and Larry Saltzman (guitar).Sullivan and Barrigan graduate from the academy - "Scotland The Brave" by the NYPD Emerald Society Pipes and Drums.Main titles / Costigan in prison - "I'm Shipping Up to Boston" by Dropkick Murphys.Costigan drives Sean to drug deals - "Thief's Theme" by Nas.Costigan breaks glass over the head of the guy who made fun of his cranberry juice - "One Way Out" by The Allman Brothers Band.Costigan beats up the Providence guys - "Nobody But Me" by The Human Beinz.Madolyn dates Sullivan / Costigan gets his hand bandaged - "The Departed Tango" by Howard Shore featuring Marc Ribot (dobro) and Larry Saltzman (guitar).Costigan meets Costello for the first time in the bar - "Let It Loose" by The Rolling Stones.Costello and French talk about Costigan - "Sweet Dreams (Of You)" by Patsy Cline.Providence corpses are found / Costigan meets Costello at his home - "Well Well Well" by John Lennon.French collects debts / Costigan knocks out Jimmy Baggs' teeth - "Bang Bang" by Joe Cuba.Costello messes with priests in restaurant / Fitzy gets busted - "Sail On, Sailor" by The Beach Boys.Madolyn moves into Sullivan's apartment - "Gimme Shelter" by The Rolling Stones.Costello goes to the opera - ""Chi mi frena (Sextet, Act 2)" (from opera "Lucia Di Lammermoor") by Daniela Lojarro, Gisella Pasino, Giuseppe Sabbatini, Michael Knapp, Michele Pertusi, Marco Chingari with the Berlin Radio Symphony Orchestra.Costigan fills out the Citizens Trust info / Costigan and Madolyn have sex - "Comfortably Numb" by Roger Waters, Van Morrison, The Band.Costigan kneecaps the bank robber - "Baby Blue" by Badfinger.Costello confronts Costigan about possibly being the rat - "Sweet Dreams (Of You)" by Patsy Cline.Costello covered in blood tells Billy to take the night off - "Tweedle Dee" by Lavern Baker.Costello and crew drive on the highway / Costello tells Sullivan to take off the tail - "I'm Shipping Up to Boston" by Dropkick Murphys.Rat on the balcony / End credits - "Sweet Dreams" by Roy Buchanan, "The Departed Tango" by Howard Shore featuring Marc Ribot (dobro) and Larry Saltzman (guitar).
The original British police force was the Constabulary of Ireland founded in 1822 (later given the royal appointment and renamed the Royal Irish Constabulary). It formed the basis for all other British police forces in the UK and across the British Empire including London's Metropolitan Police (formed in 1829) whose first 2 commissioners were both Irishmen with the necessary prior experience, Palestine Police, Royal Canadian Mounted Police etc. This established a long tradition of law enforcement running in Irish families worldwide, especially as many RIC officers emigrated to America after the violence surrounding Ireland's partition in 1922 and joined police forces there. In addition during the 19th century many corrupt, Irish dominated local governments such as New York's infamous Tammany Hall would reward their supporters with lucrative civil service jobs in the police force and fire department, often using the former as an instrument of political power.
This is left ambiguous. But given the fact that he helped the rest of Frank's crew kill Queenan, it's likely he wasn't an undercover officer. There are two hints that he may have been undercover, however. Shortly before dying; Delahunt tells Billy that he gave him the wrong address, but Billy showed up at the right one, but rhetorically asked why he didn't tell anyone. This may have been because Delahunt knew or figured out that Billy was undercover, but as he was too, wasn't going to give him up.
The news also states that Delahunt was an undercover cop, but Frank dismisses this as misinformation.
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