Film / The Departed

"We deal in deception here. What we do not deal with is self-deception."

"When I was your age they would say we can become cops, or criminals. Today, what I'm saying to you is this: when you're facing a loaded gun, what's the difference?"

— Francis "Frank" Costello

The Departed is a 2006 American crime thriller film directed by Martin Scorsese, written by William Monahan, produced by Graham King, Brad Pitt, and Brad Grey, and stars Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, and Alec Baldwin. The film is a remake of the 2002 Hong Kong crime thriller Infernal Affairs.

In Boston, Massachusetts, notorious Irish Mob boss Francis "Frank" Costello (Jack Nicholson) takes neighborhood boy Colin Sullivan (Matt Damon) under his wing, and grooms him to be his informant within the Massachusetts State Police. Colin rises through the rank and file to get himself placed on an investigation unit that is working to bring down Costello.

Meanwhile, William "Billy" Costigan, Jr. (Leonardo DiCaprio) is seeking to become a cop, despite the fact that he comes from a family that has a very disreputable past and numerous ties to organized crime. His interviewers eventually decide, when Billy refuses to be intimidated out of enlisting in the academy, to arrange for him to go to prison on a trumped-up assault charge, giving him a criminal record and street cred so that he can infiltrate Costello's crew. When both sides of the law realize the situation, both Colin and Billy attempt to discover the other mole's true identity before being found out.

The Departed was nominated for five Academy Awards and won four: Best Adapted Screenplay, Best Film Editing, Best Director, and Best Picture, losing out only on its Best Supporting Actor nomination for Wahlberg. It was the first film of Scorsese's, and to this day remains the only one, for which he won Best Director.

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This film provides examples of:

• Abandoned Warehouse: 344 Washington is completely empty.
• Adaptation Expansion: The main structure of The Departed involves rivalries between city, state and federal departments of law enforcements criss-crossing each other. This was absent in the original Hong Kong films because it's a feature of American police rather than Hong Kong police.
• Adaptation Title Change: The Departed was remade from Infernal Affairs.
• Age Cut: Colin Sullivan has one at the beginning to transition from his youth to him in the police academy.
• Alliterative Name: Madolyn Madden.
• Ambiguous Situation: Was Delahunt an undercover cop? After he's killed, he's identified as such on the news, but Costello dismisses it as disinformation planted by the authorities to throw him off the scent of the real mole. Shortly before Delahunt died, however, he confessed to Costigan that he had figured out that Costigan was undercover. "Why didn't I tell nobody?" he asks Costigan; is this a question from a morally conflicted man, or an attempt to clue Costigan in on his own secret identity?
• Animal Motifs: Rats are a common motif. The last shot features a rat scurrying across a balcony with the state house in the background. The movie is about different factions infiltrating and betraying each other.
  "Francis, it's a nation of fucking rats."
• Anti-Hero: Billy is mostly a Pragmatic Hero. He participates in some pretty bad shit and is certainly a real badass.
• Anti-Villain: Sullivan is clearly about either serving Costello's interests because he was groomed to do so or eventually protecting himself from exposure. It becomes clear later on though that his guilt over his actions begins to eat him alive.
• Anyone Can Die: Almost everyone can and will. The only named characters alive by the end are Dignam, Ellerby, and Madolyn.
• Arc Symbol: X's. Whenever one appears onscreen (usually as part of the background) with a main character in the frame, that character is going to die, usually very soon after.
• Arc Words: "No-one gives it to you. You have to take it."
• Artistic License – Law Enforcement:
  • Colin Sullivan is assigned to a detective role immediately upon graduating from the police academy for the Massachusetts State Police. In the real Staties, troopers are immediately assigned to field training in uniformed patrol upon graduation and can expect three to five years of patrol work on the roads before they are even considered for any other role or promotion in the agency. The script mentions that four years passed between Sullivan's graduation and him being selected for the investigation unit, but this is never mentioned onscreen in the final film.
  • Also, Sullivan is shown giving orders to Sergeants and other ranking officers. In the Massachusetts State Police, you have to spend five years as a Trooper before being promoted to Trooper First Class, and even then they would not outrank a Sergeant. For him to try ordering around Sergeants would have ended in him being told to go fuck himself, no matter what his job was.
• Asian Speekee Engrish: Costello says, "No tickee, no laundry," to insult the Chinese gangsters with the broken English and Chinese laundry stereotypes.
• Asshole Victim:
  • The police's view on Myles Kennefick, killed by Costello's crew. Captain Ellerby points out, "We're not here to solve the case of the missing scumbag. We're here to nail Costello."
  • Frank Costello himself gets killed by Colin Sullivan. And Fitzy and the rest of Costello's men.
  • And at the end, Barrigan and finally, Sullivan himself.
• Ate His Gun: Mr. French has already been shot and then is trapped in his crashed/burning car, with the State Police closing in. "... Fuck it."
• Bait-and-Switch Accusation: Costigan exits the gang's headquarters only to be accused of being a cop by two "fellow" members at the gate. Billy doesn't flinch and asks "What?" upon which the two thugs reveal that they were just playing a game and jokingly called everyone passing by and ignoring them to be cops. Costigan and the audience take a deep breath.
• Battle of Wits: Sullivan vs. Costigan — find out who the other guy is without giving away your own identity. Begin.
• Becoming the Mask:
  • Heavily discussed by Costigan, where he worries that the horrible things he has to do while undercover are actually making him more of a horrible person, which culminates in him being unable to trust the police department at all; he asks to resign rather than be reinstated after Costello's death ends his mission, and upon realizing that Sullivan is a mole he immediately goes rogue to try to deal with him rather than even considering reporting him to anyone else in the department.
  • Sullivan experiences the reverse. Costello notes that he's getting a little too comfortable with his cushy surroundings, his social aspirations and his relationship to a pretty psychologist and seems to want to become a Social Climber. The latter keeps reminding Sullivan who he's working for. Sullivan is initially loyal to Costello and totally corrupt but he eventually rats out his crew and Costello when he finds out that Costello is an FBI mole and he ends up parlaying his betrayal into a heroic platform and a legitimate legal or political career, which ends of course thanks to Costigan and Dignam.
• Being Evil Sucks:
  • Sullivan hates working under Costello and likes the legitimate life, if only for social reasons rather than moral ones. In the end, all his ratting for Costello turns out to be for nothing, because Costello never had real loyalty to Sullivan and would have ratted him out to the FBI, and indeed had incriminating evidence and a second mole as insurance. He loses the woman he loves when she learns that he's a mole, and he ends up alone, and then he dies.
  • Likewise, Costello himself while embodying the gangster hedonistic lifestyle seems to be bored and tired of his lowlife operation which only survives and escapes the police because he's a stooge for the FBI. He seems to want bigger things from Sullivan but gets distracted from his focus and ends up leading his men into a suicide mission; his organization is infiltrated by two different police departments under his nose; and he ends up being killed by his own protege when he becomes the liability.
• Being Good Sucks: Costigan remains loyal to the police throughout the whole movie. He spends time in prison and gets a criminal record to gain street cred so he can infiltrate Costello's organization, is roundly abused by his allies (especially Dignam), and is finally murdered ignominiously for his trouble.
• Berserk Button: Don't ask Costigan if he's got his period.
  • In the final confrontation between Sullivan and Costello, Sullivan not-so-subtly implies that Costello is infertile. Costello's immediate reaction is to point his gun at Sullivan, who in turn shoots Costello dead.
• Big Bad: Frank Costello, The Don all this infiltration is centred around. Though by the end, Sullivan becomes this.
• Big Fancy House: Apartment, but close enough. Sullivan lives in a luxurious apartment courtesy of being on Costello's payroll. Costello himself has a very nice beachfront one.
• Big "SHUT UP!": Costigan to Sullivan, punctuating each syllable with a punch to the face.
• Bilingual Bonus: Anyone who can understand Cantonese will get a hint that Costello is an FBI snitch well before English speakers do.
  Chinese Mob Boss: What is wrong with you?! I've been waiting and waiting. This guy's from the government, man! If he gets caught he'll have to kill himself.
  Costello's Translator: The boss doesn't think it's wise to bring automatic weapons. Are you crazy? Put your weapons away! Quick! Come on!
  Chinese Mob Boss: Put the guns down.... I'm ordering you, check the goods.
• Bittersweet Ending: Almost everybody dies. Sullivan kills Frank after finding out Frank was informing on the FBI and fearing he'd rat him out. (If he had to he probably would have, given the tapes he made of their conversations.) Costigan after outing Sullivan is killed by the other mole, Barrigan, who Sullivan was unaware of was working for Frank too; Sullivan kills him to cover his tracks since the department is unaware there is more than one mole, and Dignam kills Sullivan after Costigan has the evidence incriminating Sullivan sent to him. A lot of good people did die, but all the bad people did too. A major theme of the movie involves those confined to the life they're forced to live given freedom and release by death. Colin's life has gotten so miserable as a result of his actions by the end of the movie that when Dignam shows up at his apartment, it becomes crystal clear that the only thing left that Colin wants is to die, and die he does. Before that, it's also hinted that Colin felt guilty about Billy getting killed and his recommending him for the Medal of Merit was also to give everything Billy worked and died for meaning.
• Black-and-Gray Morality: Costello is a bad guy but most of the society around him is pretty corrupt. The cops are more interested in their bureaucratic in-fighting than in catching bad guys, and for young kids in the neighborhood there isn't anyone to turn to.
• Black Comedy: Costello provides many moments of morbid humor. In one scene, he's yammering about basically nothing to Billy when he pulls out a severed human hand in a plastic bag, just to make a point. In another scene, he comes out of the back of a bar, looking a little addled, his arms soaked in blood to the elbows, and tells Billy that he can have the night off.
  Frank Costello (after shooting a woman): She fell funny.
• Black Dude Dies First: Inverted. Trooper Brown is the last (non-corrupt) cop to die.
• Blast Out: At one point a squad of cops follow Costello's men, with Sullivan ordering them to stay back and watch. Eventually they get fed up with this, ignore Sullivan's orders and charge in with guns blazing. The result is multiple casualties on both sides.
• Blood from the Mouth:
  • Costello following his gut wound. He literally gushes blood once Sullivan double-taps him.
  • Delahunt after the shootout, when giving his Deathbed Confession to Billy.
• Blowing Smoke Rings: We see Billy blow some, as a manner of projecting the ease he does not actually feel while in Costello's gang.
• Book Ends: Involving ISO-Standard Urban Groceries. At the beginning of the film Frank Costello instructs the store clerk to fill a white paper bag with various groceries for the kid Colin Sullivan, notably a couple of loaves of bread and a couple of quarts of milk. In the last scene of the film we see adult Colin Sullivan walking into his apartment with a white paper bag full of groceries, two of the items you can see in the bag during this scene are a couple of loaves of bread and a couple of quarts of milk.
• Boom, Headshot!: Costigan, Brown, and Barrigan all get one in less than a minute. Sullivan eventually gets his in the finale.
• The Cameo: Massachusetts State Police Major Thomas B. Duffy, most well-known for being involved in the Whitey Bulger case, appears as the Governor of Massachusetts, swearing in a group of police academy graduates.
• Can Always Spot a Cop: Played with. In one scene, two members of the criminal gang are hanging out on the street and one of them starts joking that he can always spot a cop. According to him, if someone ignores you, they're a cop. He then proceeds to say that every single person walking by is undercover because they're all ignoring them. As a twist, he might actually be an undercover police officer himself.
• Cacophony Cover Up: One gangster is shown out in the street, tossing cherry-bombs, apparently for fun. We realize in the next scene that he was covering for the sounds of gunfire.
• Canon Foreigner: Sgt. Dignam has no equivalent character in the original Infernal Affairs film, where the police captain is the only person who knows the police mole's identity. This makes Dignam's reappearance at the end more predictable for people who have seen the original.
• Captain Smooth and Sergeant Rough: Dignam is much more coarse and rough when compared to Captain Queenan.
• The Chains of Commanding: Discussed. Frank Costello is Properly Paranoid about having rats in his criminal organization. While talking to Costigan, who is indeed a police informant, he asks if Costigan thinks he could be boss. Costigan affirms that he probably could, but adds that he'd really rather not have the constant pressure and paranoia that somebody in Costello's position has to deal with.
• Chekhov's Gun: The envelope. Sullivan carelessly leaves the "CITIZENS TRUST" envelope on his desk. Costigan sees it, recognizes it, and realizes that Sullivan is The Mole in the police.
• Chekhov's Gunman:
  • Barrigan, literally.
  • Dignam, who walks out of the film 40 minutes before the end seemingly for good, letting Costigan and Sullivan face off uninterrupted, before coming back in at the very end to wrap up the plot.
• Chewing the Scenery: "I smell a rat." In fact Costello almost literally chews the scenery when doing his bizarre imitation of a "gnawing, cheese-eating fucking rat."
• Chronic Backstabbing Disorder: Costello. He even screws over the Chinese government when he gets a chance; likewise, the FBI in turn screw over the Staties; and Sullivan betrays Costello and finds out that Costello never trusted Sullivan and had a second mole to keep an eye on him.
• Cluster F-Bomb: This is the movie with the most uses of the word "fuck" and its derivatives (237) to win the Best Picture Oscar. Most contributions come from Sir Swears-a-Lot Dignam.
• Composite Character: Madolyn is a combination of therapist Dr. Lee, the undercover cop's love interest, and Mary, the infiltrator's girlfriend, creating a Love Triangle where there had been none before.
• Country Matters: This gem:
  Oliver Queenan: Do you know what we do here? My section?
  Billy Costigan: Sir, yes, sir. I have an idea...
  Sean Dignam: [interrupting] Whoa, whoa, whoa. Let's say you have no idea and leave it at that, okay? No idea. Zip. None. If you had an idea of what we do, we would not be good at what we do, now would we? We would be cunts. Are you calling us cunts?
  Oliver Queenan: Staff Sergeant Dignam has a style of his own. I'm afraid we all have to get used to it.
• Crapsack World: The Boston underworld seen onscreen is a horrible place of twisted morality and allegiances. There isn't much difference between the good guys and the bad guys. One can argue that cops like Dignam and Ellerby are little better than Costello. Costello can also blackmail the Catholic Church because of their cover-ups of child sex abuse. Nearly every major character is killed; Costigan, Sullivan, Queenan, Costello, French and Costello's crew to a man. There are few truly altruistic characters; in fact, Madolyn may be the only one, and possibly Queenan. There's also no hope among anyone that things will get better.
  Martin Scorsese: What I immediately related to in the material of Bill Monahan's script...As we were making it I'm realizing that we're in a moral Ground Zero...it's a world where morality no longer exists. Costello knows this. I think he's almost above it, he knows that God doesn't exist anymore in the world that they're in and it's the old story, in order to know you have a problem first you have to know you have a problem...I think for me it just is a sadness and a sense of despair since we've been in this situation since September 11th and somehow this all came together and that's what kept me going in depicting this world sort of like a moral Ground Zero.
• Creator Cameo: Producer Graham King appears in a photograph as Costigan's deceased father.
• Cruel Mercy: Once he sees the jig is up, Sullivan begs Costigan to kill him. Response: "I am killing you."
• Cultured Badass: Costigan got good marks and doesn't have to be a cop since he's very well qualified. He can also quote Nathaniel Hawthorne.
• Cut His Heart Out with a Spoon: "I'm gonna tear your fucking arm off and shove it up your fucking ass!!" (And this is a cop talking.)
• Da Chief: Captain Queenan.
• Dead Man's Trigger Finger: After getting shot and rolling into the dumpster, Costello fires his gun reflexively, causing Sullivan to fire several more shots at him.
• Deadpan Snarker: Sergeant Dignam.
• Deathbed Confession: Delahunt, bleeding out from a shot to the chest that isn't going to get treated, reveals that he knows Costigan is undercover, and and may in fact have been trying to identify himself as a cop as well (see Ambiguous Situation).
• Death by Adaptation: In Infernal Affairs, the character equivalent to Sullivan is a Karma Houdini who walks away scot-free by the end of the movie. In The Departed, he is killed by Dignam, a character who has no counterpart in the original, and who's added to the adaptation for this purpose alone.
• Death Is Dramatic: Averted. One of the three leading actors is killed instantly with no warning whatsoever.
• Deceased Fall-Guy Gambit:
  • After his death, Costello's mook Delahunt is identified on the news as a cop. Costello dismisses the story and claims that it's a lie meant to make his whole organization panic. It's possible that if Delahunt was in fact a cop, his identity was intentionally made public in order to take the heat off of Costigan and make Costello believe that the only cop in his organization was gone.
  • After Barrigan's death Sullivan tries to make him appear responsible for all of the police leaks to Costello, covering up Sullivan's role working as Costello's mole.
• Deconstruction: A standard for Scorsese, but this one attacks a lot of genre tropes:
  • The movie shows the dangers of an undercover cop. There's not only the risk of being caught, but the risk of being killed while undercover, with the only people who can verify your existence also dead, your records deleted and you are forced to end up Becoming the Mask for real. Costigan barely averts this by the end, and gets desperate knowing that eventually he would have to get his hands dirty.
  • A lot of old gangster movie tropes are overturned. Police work isn't an avenue for redemption, but just a line of work like any other. When Costigan first meets Queenan and Dignam, they bluntly tell him that Costigan's idea about law enforcement being a way of redeeming the family name is going to fold under the boredom and monotony of the job until eventually Costigan realizes that he has much better prospects than simply being a state trooper and quits the force. In the end, Costigan's desire for redeeming his family name winds up getting him unceremoniously killed. Sullivan sees law enforcement as a cynical career move and betrays his criminal allies not out of moral outrage but to cover his tracks. As for the Church and reforming priests trying to reform criminals a la Angels with Dirty Faces, here they are pedophiles who get blackmailed by an Ax-Crazy sleazebag mob boss. Likewise, most of the problems happen because the Staties, Boston P. D., and the FBI fail to collaborate with each other and screw over each other rather than do what they are supposed to do.
  • The lack of communication between departments and obsession with a need-to-know basis makes for Poor Communication Kills as much as it keeps informants safe. Costigan goes through a lot of trouble trying to find out the mole due to his only liaisons being his two superior officers, who are the only people who know he's even a cop to begin with. The biggest impediment the cops have in catching Costello isn't the mob, but rather their own allies in the FBI, who have nabbed Costello as a stooge and are desperately keeping him alive to the point of going against the BPD. All in all, the situation's lack of communication between parties doesn't so much keep security as it does encourage paranoia and distrust.
  • Backstabbing pretty much everyone like Sullivan does is eventually going to stop working. His betrayal of Costello, Barrigan, Queenan, and his fraudulent story about how Costigan and Brown were killed likely clued Dignam in that he was the rat, even before Madolyn is implied to have sent him proof. The amount of death that surrounds Sullivan (that he always seems to have the perfect explanation for) simply becomes more and more impossible to explain away.
• Detective Mole: Sullivan.
• Dirty Cop: Colin Sullivan. Ironically, he's not very well liked within the department because everyone thinks that he's using his squeaky clean record (and a whole lot of asskissing) to get ahead.
• Disappeared Dad: One of the major themes of the film.
• The Dragon: Mr. French is Costello's.
• Dramatic Irony: On the way to a meet, Queenan confidently tells Costigan "I don't have a tail." He does have a tail, and this leads directly to his death when Colin gets word from the tail about where Queenan went, and passes this info to the bad guys.
• Dragon Their Feet: Reversed and played straight at two different points.
• Dr. Feelgood: Enforced by Costigan. Madolyn doesn't want to talk about drug prescriptions but Costigan uses a Bavarian Fire Drill to press Valium from her. When she offers him two pills, he refuses to take them.
• Dropped a Bridge on Him: Costigan is abruptly shot in the head in deliberately un-dramatic fashion. Brown and Barrigan die in the same manner moments afterwards.
• Embarrassing Old Photo: It's only Sullivan who thinks this way about Madolyn's childhood photograph.
• Enhance Button: Subverted when zooming all the way in on security camera footage does not enable Sullivan to discern any more details about his pursuer, keeping him from identifying Costigan.
• Establishing Character Moment: Costigan and Sullivan's reaction to Madolyn's childhood photograph highlights the difference in the two characters. Sullivan is more concerned about his career and his 'image' and so he doesn't want that picture in his apartment. Costigan really just likes Madolyn so he can appreciate a cute picture of her childhood on the wall.
• Establishing Character Music: Costello is introduced in The '70s to "Gimme Shelter" by The Rolling Stones (Band).
• Even Evil Has Standards: When Costello executes two people on a remote beach by shooting them in the back of the head, he notes that the woman "fell funny", and starts laughing. Costello's right-hand man Mr. French gives him a disturbed look and voices to his boss that he might want to talk to someone.
  Mr. French: Frank, you gotta see somebody.
• Every Car Is a Pinto: During the climatic drug deal, Mr. French drives his car into a container upon which it catches fire and explodes.
• Everything's Louder with Bagpipes: At the graduation for the cadets.
• Evil Counterpart: Sullivan to Costigan. At one point, they even wear practically identical clothing. Sullivan was a poor orphan and sees Costello as his Parental Substitute (albeit an abusive one^note "Is that what this is about? All that murdering, and fucking, and no sons.") and sees his infiltration into the Massachusetts state police as a chance to be the Social Climber, Billy on the other is born into a slightly well-off family with mob-connections and sees joining the police as a way to prove that he's different from his family, which he can only do by parlaying his family's reputation by infiltrating Costello's outfit as a police mole.
• Evil-Detecting Dog: A dog shies away from Sullivan at the end of the film.
• Evil Phone: Played straight when Costello is on the other end. Subverted with Queenan's phone.
• Face Death with Dignity: Sullivan ultimately meets his fate with a dejected "Okay..."
• Failed a Spot Check: As a state police detective Sullivan's address would have been a matter of public record within the department. Somehow nobody - not even Madolyn - thought to question how a police detective could afford a massive luxury condominium in the heart of Boston with a view of the State Capitol. Even the real estate agent seems to suspect something is amiss but doesn't bother to turn down a sale.
• Feed the Mole:
  • In order to find the rat at the SUI, Costigan tells Dignam to slip the info about fictitious cameras being installed at Costello's place: "Flush it down the pipe, see if it comes out on my end."
  • Costello tells Costigan about a drug boat coming into Gloucester, knowing that if the police find out about it, that means he's the rat. By this point, Costigan is paranoid about the informant in the police department, and decides not to tell Queenan or Dignam. So when Sullivan tells Costello the police haven't heard about it, Costello thinks that Costigan is innocent.
• Fingertip Drug Analysis: Costello tastes the cocaine during the drug deal.
• Feet-First Introduction: At the end. The Feet-First Introduction of Dignam waiting in Sullivan's apartment is not just dramatic; it shows that Dignam is wearing baggies around his shoes to make sure he doesn't leave any evidence in the apartment.
• Flock of Wolves: Fitzy and Mr. French are the only two named members of Costello's crew who definitely aren't undercover cops or confidential informants. And that's including Costello himself. Delahunt may or may not be undercover: see Ambiguous Situation.
• Foil: All over the place:
  • Costigan and Sullivan are both Southie Irish kids. Costigan comes from a corrupt mob-connected family but honestly wants to be a cop and goes undercover into the very life he hates as part of a Redemption Quest. Sullivan is a poor slum kid who seems to have a squeaky clean and crime free record, but has been under the influence of the ruthless gangster Costello ever since Sullivan was a kid, and becomes Costello's mole within the police.
  • More generally there's the fact that the cops and the criminals are ultimately poor kids from the same Southie neighbourhood more or less, and that the only real options for them to be The One Who Made It Out is a career hunting each other on opposite sides of law:
    Costello: When I was your age they would say we can become cops, or criminals. Today, what I'm saying to you is this: when you're facing a loaded gun, what's the difference?
• Foreign Remake: Of Hong Kong's The Infernal Affairs Trilogy.
• Foreshadowing: As pointed out by Cracked, almost every death is preceded by an X in frame. Like, window frames, the airport supports behind Costigan when he talks to Dignam on the phone, the floor pattern outside Sullivan's apartment, a bit of tape in that elevator Sullivan and Costigan ride.....
  • Also, several times earlier in the film there are closeups of people pushing buttons in elevators, and the floor indicators ... foreshadowing the climactic scene in the building under construction where Brown, Costigan and Barrigan all die.
  • In the scene between Ellerby and the FBI, the fact that the cameras are angled so as to create a huge blind spot, foreshadows that Costello is a FBI informant and the Feds are protecting their stooge.
  • Dignam tells Costigan that he's "the best friend he [Costigan] has on the face of this earth." It's easy to write this off given Dignam is in the middle of a massive tirade against Costigan. After Costigan's death, Dignam - by this point Costigan's only surviving ally in the police due to Queenan's death - sees to it that his death is avenged after Sullivan seemingly escapes justice.
  • During the dinner at the restaurant where Costello tells Costigan that he smells a rat, Costigan warns Costello that one of his guys is gonna pop him because of his FBI informant status of giving them up. He’s right, though it’s Colin Sullivan who does it.
  • The first time Costello calls Sullivan for an update, Costello is angry because Sullivan has not kept him in the loop on his psychiatrist girlfriend and the snazzy new apartment. When they meet again face to face in a porn movie theater he owns and Sullivan informs him that he’s being reassigned to hunt himself, Costello nonchalantly and calmly replies he already heard. Sullivan is surprised that Costello already knew about this reassignment and isn't angry about not being informed in advance. Costello had learned about this from Barrigan, his other mole in the Staties that he uses to keep tabs on Sullivan.
• For the Evulz:
  Billy Costigan: Look, you're seventy years old, Frank. I'm just sayin', okay? One of your guys is gonna pop you. One of your guys is gonna pop you. As for running drugs, what the fuck are you doing? What are you doing? You don't need the money or the pain in the ass, and they will catch you.
  Frank Costello: I haven't "needed the money" since I took Archie's milk money in the third grade. Tell you the truth, I don't need pussy anymore either... but I like it.
• For Want Of A Nail: Sullivan strolls out of his meeting with Queenan and flirts with the secretary which means he doesn't spot Costigan waiting and know he was already in the police and interviewed by Queenan for his special unit.
• Freeze-Frame Bonus: Towards the end of the film, when Costello is arguing with his mistress, she's reading a book that is apparently about getting pregnant. Whether she's pregnant or trying to get pregnant is not revealed.
• "Friends" Rent Control: Lampshaded and justified. A realtor casually questions how an unmarried state police detective can afford an extravagant apartment with a view of the Capitol Building.^note The realtor notes that the apartment is near the Beacon Hill neighborhood, where apartment prices can easily climb into the seven figures. Sullivan, of course, can afford it due to being Costello's mole.
• Get It Over With: In the final scene, Colin returns to his apartment to find Dignam, wearing hospital slippers to hide his shoeprints and pointing a loaded gun in his face to avenge his dead comrades. He hesitates as if to say, "Any last words?" But Colin is resigned to his fate and simply mutters a disgusted "Okay." Dignam promptly pulls the trigger and flees.
• Good Cop/Bad Cop: When Costigan is being interviewed about his application by Queenan and Dignam, Queenan plays the good cop while reading Costigan's application and Dignam plays the foul-mouthed bad cop trying to discourage Costigan from signing up.
• Good is Not Nice: Dignam and to a lesser extent, Costigan.
• Greater-Scope Villain: The FBI. Costello is their stooge, and the Interservice Rivalry and Jurisdiction Friction they facilitate leads to Costello escaping the meeting with the Chinese gangs, Costigan extending his time undercover and finally Sullivan betraying Costello and his crew to cover up his actions, and generally the massive Gambit Pileup that leads to everybody dying at the end.
• Group Reacts Individually: Costigan and Sullivan's Establishing Character Moments to Madolyn's Embarrassing Old Photo of her childhood highlights the difference in the two characters. Sullivan is more concerned about his career and his "image" and so he doesn't want that picture in his apartment. Costigan really just likes Madolyn so he can appreciate a cute picture of her childhood on the wall.
• Had to Come to Prison to Be a Crook: Invoked when Costigan gets four months in prison on a fictional assault conviction so that he has a criminal record, which combined with his family's own ties to organized crime, give him enough street cred to infiltrate The Irish Mob.
• Hahvahd Yahd In My Cah: Naturally Boston accents feature prominently. You even get the real package, since Matt Damon and Mark Walhberg are native Bostonians.
• Hair-Trigger Temper: Costigan, Costello and Dignam all have this, albeit to different degrees. Costigan may have initially been faking some of his as part of selling his cover as a violent would-be criminal, but the intense stress and psychological pressure from his prolonged undercover assignment and the danger he is in at all times means that by the end he has it for real.
• The Hero Dies: Costigan is shot in the head by Barrigan.
• Heroic BSoD: Costigan and Sullivan have a simultaneous one when they are on the phone together after Queenan's death. Although Sullivan's is probably more of a villainous version.
• Hired to Hunt Yourself: Sullivan, looking for a mole within the police department. He Lampshades this while talking to Costello about it.
  Sullivan: Hey, Frank, I gotta find myself.
• Hollywood Hacking: Sullivan deletes all of Costigan's records to hide his own tracks. Needless to say, this would be impossible in real life, as very, very few users in any large organization have full Erase privileges over employee records, and even if records were somehow erased, they could easily be restored from automatic backups. Then there's the fact that many systems like this keep logs of who did what in the system, meaning that even if Sullivan deleted Costigan's records, there would be a record of him deleting the information.
• Hollywood Silencer: In the final scene, the gun with which Dignam shoots Colin makes a much quieter sound than an actual pistol with a silencer would make.
• Hope Spot: Costigan has Sullivan under arrest, the good guy wins, happy ending—and then the other mole in the police department shoots Costigan in the head.
• Hypocrite:
  • Frank told Sullivan as a kid not to let anyone tell him what to do and scoffing at the legitimate authorities in society. Frank's an FBI rat and can only get away with what they allow him to, or can cover for.
  • Sullivan and Costigan calling other characters "rat fucks" is pretty hypocritical.
  • Sullivan giving an eulogy to Costigan who he makes into a martyr, and then attending his funeral is the height of hypocrisy. Madolyn walks away from him in total disgust.
• I Can Explain: Sullivan tries this on Madolyn after she has listened to the tapes and figured out who her lover really is. The break-up is inevitable though.
• If You're So Evil, Eat This Kitten!: Billy Costigan is constantly being tested by Costello. Though by the latter half of the movie this seems to be Costello being a Troll more than suspecting Costigan specifically; Costigan manages to get on Costello's good side to the degree that he avoids suspicion as the mole.
• I'll Kill You!: Billy says this to Sullivan in the elevator, although it's clear that he's speaking metaphorically.
• I Never Said It Was Poison: Before dying, Delahunt figures out that Costigan is an undercover cop because he is at the place where the other gangsters were congregating to catch the mole, even though Costigan was accidentally given the wrong address.
  • A more subtle example happens when Costigan tells Costello, "I'm not the fucking rat!" and Costello responds, "You agree there is a rat?" Costigan says, "You said there is one, all right?"
• The Infiltration: Costigan plays the trope straight when infiltrating the Boston underworld. Sullivan plays The Mole.
• Informed Kindness: Played for laughs. After Dignam gives an extremely rude briefing, his colleague, Ellerby unconvincingly says: "Normally, he's a very, uh... nice guy. Don't judge him from this meeting alone."
• Instant Death Bullet: Played straight for at least four characters, including major ones.
• Internal Affairs: With a heavy dose of irony. Everybody hates Sullivan because he and "Internal Investigations" are up everybody's ass trying to find The Mole in the police department. Nobody knows that in reality he was hired to hunt himself.
• Internal Reveal: Two-way reveal. Costigan comes to the office to finally reveal his identity to Sullivan. Then Costigan sees the envelope and figures out who Sullivan is.
• Interrupted Intimacy: Sullivan and Madolyn are about to go dirty in his kitchen but they get interrupted twice, first by a phone call and then by the movers at the door.
• Invulnerable Knuckles: Averted. Costigan injures his left hand punching out a goon in a bar fight and has to have it put in a cast. Which comes back to bite him when Costello thinks the cast is a ruse to conceal a wire and inspects it rather roughly. Funnily enough, this is based on a scene in the original film where the cast is fake.
• The Irish Mob: Costello (partially based on real-life Irish mobster Whitey Bulger) heads it.
• Iris Out: Used twice.
  • There is an Iris In effect early on in an Establishing Shot of Sullivan in front of the SUI building.
  • An Iris Out two-third into the movie, in a shot of Sullivan sitting at his office desk.
• ISO-Standard Urban Groceries: At the end, Sullivan carries one of these bags into his apartment. He gets shot by Dignam, and the groceries do end up all over the floor. The original script even called for the rat that comes out to start nibbling on a fallen bagel.
• Jerkass: Sullivan and Costello.
• Jerk with a Heart of Gold: Staff Sgt. Sean Dignam. He is a rude, obnoxious bully who needlessly antagonizes everyone he comes in contact with, but is dedicated to the job and fiercely loyal to Queenan. And when Costigan, who he really antagonized is killed, he murders Sullivan to make sure that some kind of justice is done.
• Jurisdiction Friction: There's a small bit between Sullivan and members of the Lynn police when they find the bodies of the two Italian mobsters who were sent to kill Costigan. Justified too, since in Massachusetts, the Staties have automatic jurisdiction in all homicide investigations in the Commonwealth except in Boston, Springfield, and Worcester, where the local police department has first dibs.
• Just a Gangster: Costello can't think beyond being an old fashioned gangster, and he lives and acts like a 30s gangster transplanted into the early 21st century. He and his outfit only survive as long as they do because he's a stooge for the FBI, who use Costello to crack down on other, more dangerous gangs like the Chinese, who are involved in bigger schemes. Sullivan, who is a cold Social Climber, wants to study law and become a politician, but Costello sneers at his legitimate ambitions, or living any life other than his old school gangster ways. In the end Sullivan finds out about Costello's complicity with the FBI, and wipes him and his whole gang out so Sullivan can cover his tracks and try to move ahead with his legitimate ambitions.
• Karma Houdini Warranty: At the end it looks like Sullivan is going to get away scot-free. Then Dignam makes sure that can't happen.
• Karmic Death: Costello is killed by Sullivan, the very same person he groomed to be his Mole in the Massachusetts State Police. Bonus points for being a reversal of how Queenan died.
• Knee-capping: Costigan uses this type of Mutilation Interrogation technique on one of the baddies. Apparently it hurts badly if you don't go into shock.
• Lecture as Exposition: Capt. Ellerby gives the cops on the task force a briefing on Costello and his gang that explains for the audience just who Costello is and who his principal lieutenants are.
• Life Imitates Art: In-Universe example. The rat at the end mirrors the drawing Frank is working on as he waits for Bill in the restaurant scene - the Golden Dome surrounded by rats.
• Like a Son to Me: Costello tells this to Sullivan, after Sullivan finds out that Costello was an FBI informant.
  Costello: You know I'd never give you up. You're like a...
  Sullivan: What, like a son? To you? Is that what this is about? All that murdering and fucking, and no sons.
• The Loins Sleep Tonight: Sullivan's erectile dysfunction. Madolyn makes a comment about 'last night' and its 'very common among men'. Possibly a case of Sexual Karma.
• Love Triangle: Between Madolyn, Sullivan and Billy. Added for Rule of Drama, there was no such thing in the original.
• MacGuffin: Lampshaded: The microprocessors. "Yes those. I don't know what they are, you don't know what they are, who gives a fuck?".
• Male Frontal Nudity: Invoked: Costello whips out a fake penis in a pornographic movie theater at one point during a covert meeting with Sullivan.
• Mercy Kill: A major theme of the movie is death being a release from one's burdens.
  • Billy is relieved of his frustrating and miserable existence trying to live down his family's reputation when he's shot in the head in the end. While it's partially to avoid the truth about himself coming out too, Colin also recommends Billy for the Medal of Merit and gets him a hero's funeral.
  • Colin's life blows up so badly after the fallout of everything that he doesn't even bother trying to talk his way out of Dignam shooting him in the head.
• Mexican Standoff: Between Costigan, Sullivan and Brown during the Rooftop Confrontation.
• "Mister Sandman" Sequence: The opening montage set to "Gimme Shelter".
• The Mole: Sullivan is a mole planted by Costello to be his informer within the police, while Costigan works the other way as a mole planted by the cops to be an informer within Costello's crew. This gets more complicated when we find out that Costello is an FBI informant, while Delahunt, one of his mooks, may have been a Boston Police Department mole. Later, Costigan barely has time to realize that Costello also had a second mole in the Staties, Barrigan, who was there to keep an eye on Sullivan.
• Mole in Charge: Sullivan, Costello's mole in the State Police, who's put in charge of finding the mole in the State Police.
• Must State If You're a Cop: During the talk with his criminal cousin Sean on the balcony, Costigan is asked to tell if he is a cop, which he denies. This one is justified since Costigan's participation in the police academy couldn't be concealed.
• My Card: Madolyn hands her card to Sullivan in their Meet Cute scene at the elevator.
• Near-Villain Victory: Sullivan almost gets away clean. Then Dignam puts a bullet in his brain.
• Newscaster Cameo: The TV news broadcaster who talks about the discovery of Delahunt's body in the Boston mudflats is Frank Mallicoat, who at that time had been a newscaster on Boston TV for 20 years.
• No-Holds-Barred Beatdown: For the scene where Billy Costigan beats up the two Italian guys in the store.
• Not His Sled: Sullivan's death plays out differently compared to the original Hong Kong version.
• Number Two: Dignam for Queenan.
• Obfuscating Stupidity: Early on in the film Costigan pretends to be significantly less intelligent than he is, in hopes that Costello won't consider the possibility that he's the mole.
• Obstructive Vigilantism: Dignam keeps mum about what he knows, and in the end he just shoots Sullivan.
• Oddly Small Organization: The Boston mob, or what we see of them, is composed of five members, twenty to forty percent of whom are undercover cops.
  • A few others, including Costello's back-up crew, are often seen hanging around in the background, but none are given any significant screentime or dialogue, effectively making them little more than set dressing.
• Oh, Crap!: Costigan when he first finds out that Costello is an FBI informant. Sullivan has the same reaction later on when he too finds out.
• One-Steve Limit: Averted. There are two characters with the first name "Sean": Dignam, and Costigan's cousin.
• The One Who Made It Out: Sullivan while serving as an undercover cop gradually becomes a Dragon with an Agenda, in that he wants to study law and start a political career (as implied by his constant gazing at the Boston State Legislature), Costello keeps reminding him of who he's serving. Then Sullivan finds out Costello is The Mole for the FBI and has dirt on him that can sabotage his future, so he decides to kill everyone in Costello's organization and use the success as a platform for a new career. And he would have gotten away with it too, if it hadn't been for Dignam in his Track Pants.
• Ooh, Me Accent's Slipping:
  • Martin Sheen, God bless him, and the therapist.
  • For Leonardo DiCaprio, it is explained within the story that Costigan faked his accent based on the social situation after his parents split up. With his father down in Southie he'd assume one accent and way of acting, while he'd assume a different accent and vocabulary with his more middle-class mother.
  • Ray Winstone seems to slip back into his signature Cockney accent every other syllable.
  • On a point of interest, Mark Wahlberg and Matt Damon are immune to this because they're native Bostonians. Wahlberg specifically is even of a working class background, and he based his portrayal of Dignam on the cops who arrested him many times as a teenager... making this Truth in Television.
• Opening Monologue: Costello gives one.
• Overt Rendezvous: Whenever Queenan and Dignam need to chat with Costigan, they meet him in some park/riverbank area. This worries Costigan, because he knows if anyone sees him with them, he's got a crosshair on his forehead.
  • Going the other way, Costello points out how stupid it is for Sullivan to meet with him in a porno theater. This turns out to be prophetic, as Costigan almost catches Sullivan when he leaves.
• The Paragon Always Rebels: Each rat has their side's total trust: Sullivan is Captain Ellerby's favorite protege, and Costigan becomes Costello's most-trusted enforcer.
• The Password Is Always "Swordfish": Costigan reveals that the password for his file in the police database is his full name (including spaces). Justified, since the operation would be absolutely ruined if the wrong people learned Costigan's name anyway, why not?
• Pedophile Priest: One of Costigan's relatives is a priest instead of a criminal, but according to Dignam, he's currently "married to a 12-year-old boy, living on a beach in Thailand." Costello also blackmails a priest at a cafe who it's implied is one. He keeps ranting against the priests and chides his mistress for going to a Church that at this point is no better than him.
• Pet the Dog: Sullivan having previously deleted Costigan from the computer system after realizing the latter found out he was one of Costello's rats, reveals Costigan's identity to the other officers and recommends him for the Medal of Merit after Barrigan kills him and Brown. Costigan is given a full police funeral as a result. However, this may not be for Costigan as much as it's a way for Sullivan to make himself look even better; he's taken down a rat and restored the reputation of a falsely disgraced cop—though it's clear Colin also wants to alleviate his own guilt over the matter too.
• Police Are Useless: Inverted, that is to say that the majority of the organized crime in the film is largely facilitated by full cooperation with corrupt law enforcement personnel. Played more straight in the context of the actual clean, straight cops who end up squabbling with each other over personal things and competing rather than working together, and sabotaging their own investigations that way.
• Politically Incorrect Hero: Costigan, desperate and berserk in the finale, calls Sullivan "a faggot". That's not even getting into the poetry of Dignam's dialogue.
• Politically Incorrect Villain: Costello mentions a distaste for "niggers" in his opening monologue. While it is shown to have historical significance this racism fails to show up in any significant way within the plot — it is only used to establish, mere seconds into the movie, that this guy is not a good man. He's also pretty equal-opportunity non-PC. He throws around "guinea" (a very derogatory term for Italians) all the time and calls his Chinese contacts "Chinamen" and "chinks." Amusingly, at one point he's shown engaging in a three-way with his mistress and a black High-Class Call Girl.
• Poor Communication Kills: All the time.
  • A lot of problems could have been avoided if the various police departments collaborated with each other and shared information. Or if Dignam had contacted Costigan after being dismissed, rather than forcing the latter to go on his own and do something desperate.
• Precision F-Strike: As we all know, this is a film with a lot of swearing. However, there are a few characters who rarely do, Captain Queenan being one of them. He veers into this territory when discussing the possibility of relieving Costigan of his duties.
  Billy Costigan: Huh, what about the FBI?
  Oliver Queenan: Ehh, they're compromised.
  Billy Costigan: The... they're what?
  Oliver Queenan: They're fucked!
• Pretty Little Head Shots: Averted as most people in this movie die from getting shot in the head, and it's never pretty. It's also defied in the opening montage at the academy, as the instructor details for his cadets the effects that their hollow point ammunition would have on a human skull.
• Prison Rape: Amusingly subverted. Madolyn asks Costigan about his time in prison, leading to this exchange:
  Billy: Oh, what, you wanna hear about the showers, is that it?
  Madolyn: Why, did something happen to you?
  Billy: (Beat) ... No.
• Prisons Are Gymnasiums: Costigan is shown working out while in prison.
• Prolonged Prologue: The credits don't appear until nearly 20 minutes after the start of the movie, by which time you've already seen a flashback scene, a Training Montage, and the first plot twist.
• Properly Paranoid:
  • Costello and Queenan are both correct in their assumptions that there's a mole in their respective teams. More than one, in both cases.
  • Similarly, Costigan trusts the police department so little by the time of Costello's death that he goes rogue after discovering Sullivan is the mole and tries to deal it himself rather than report it to someone else in the department. Given that Barrigan was another of Costello's moles this turns out to be prescient, even if it didn't save Costigan's life.
• Protection Racket: Costello's Irish-American crew is involved in shaking down various businesses in Boston. In the prologue, Costello is shown doing the collecting personally before he later hands it off to his underlings as he rises in power; he meets his protege Sullivan while doing his rounds and his eventual mistress is the daughter of a corner store owner. Costigan also beats up two mafioso from Providence who pathetically attempt to extort an Indian store owner.
• Reasonable Authority Figure:
  • Captain Queenan (who also has some overlap with Team Dad).
  • Ellerby as well, despite his somewhat eccentric personality.
• Redemption Quest: In Costigan's introductory scene, Queenan and Dignam press him as to why he's trying to be a police officer and go over the numerous members of his family who were involved in organized crime. Costigan suggests that he is trying to improve his family name and disassociate himself from the disreputable backgrounds of people like his his late uncle or his cousins.
• Right Hand Versus Left Hand: What the movie amounts to. The Massachusetts State Police (Staties) send a mole into Frank Costello's organization (Costigan), he finds out that Costello is in fact a FBI mole and the Feds are screwing the Staties over. Later, Delahunt is revealed to be possibly another mole, only from the Boston Police Department. Essentially a massive Gambit Pileup between city, state, and national police who fail to collaborate with or trust each other.
• "Rise and Fall" Gangster Arc: Sullivan's character arc. Sullivan is taken under the wing of gangster Frank Costello at an early age and groomed to eventually become Costello's mole in the police. The first half of the film features him skyrocketing to prominence within the force, using his connections to pin Costello's crimes on scapegoats, getting engaged and gaining a fancy apartment. However, things start coming undone when Costello tasks Sullivan with finding the police informant in his gang (the other main character, Billy Costigan) - and the police task Sullivan with finding the mole in the department. As a result, Sullivan is drawn into a deepening web of lies and paranoia that results in him having to screw over both factions; in the process, he loses his girlfriend, his nerves, and very nearly his life. Just when it looks as if he's managed to beat the odds and get out in one piece, he ends up getting shot dead by the one cop who distrusted him from the very beginning.
• Rooftop Confrontation: Costigan and Sullivan have one after they have figured each other out.
• Sanity Slippage:
  • Costello becomes more unhinged as the story progresses. Which is disturbing to see, since he's not terribly sane to start with.
  • Costigan struggles with this from time to time.
• Say Your Prayers: Queenan crosses himself when he expects that he'll soon be killed by Costello's men.
• Secret Test: Costello tells Billy about how he's going to take his "new guys" for some operation in Gloucester. Costigan sniffs this out as possible disinformation and asks Queenan for a meet. When Sullivan doesn't hear anything about Costello taking his new guys to Gloucester, he incorrectly concludes that Billy isn't the mole.
• Self-Offense: Sullivan stabs some random restaurant worker in the chest, believing him to be Costigan.
• Sexual Karma: Costigan is a love machine. Sullivan, meanwhile, seems to have issues with erectile dysfunction. Guess which one is the hero. More subtly applied with Costello, who has an active sex life (even at his old age) despite being a far from exemplary individual. However, it's strongly implied that he's infertile. Word of God says that Costigan is actually the father of Madolyn's child.
• Shoot Him, He Has a Wallet!: A non-fatal variant when, during a shakedown, Costigan pistol-whips a bookie and knocks a couple of his teeth out. "I was goin' for my fuckin' cigarettes!"
• Shout-Out:
  • The scene in the graveyard has significant visual parallels with a scene in The Third Man the Love Interest walks past the expecting hero who stands on one side. Only here she's mourning The Hero rather than the villain.
  • When a character is about to die, an X appears somewhere in the frame. This is a Shout Out to Scarface by Howard Hawks.
  • We briefly see a character watch John Ford's The Informer on TV, a movie set in Ireland about informers ratting each other out.
  • The finale with a rat is likewise a reference to All That Heaven Allows where a deer's sudden appearance in the background for Rule of Symbolism is mockingly invoked with even more literal meaning.
  • The film makes many references to other Film Noir about police informers, such as White Heat and Samuel Fuller's Underworld U.S.A..
  • The constant shots of the Boston State Legislature is one to Richard Fleischer's The Boston Strangler.
  • The cues when Colin is getting into the shower—the shower curtain hooks screeching against the metal rod, the water shooting straight out from the shower head—are taken directly from Psycho and its infamous shower scene. Colin doesn't get stabbed to death but he does meet disaster of a different sort, as that is the moment when Madolyn listens to the recording and realizes that Colin is a criminal.
  • That recording Madolyn listens to is inside a CD case of Exile on Main St..
  • Japanese horror film Audition is on the TV in one scene were Colin and Madolyn are talking in Colin's apartment.
  • The porn theater scene is probably one to Taxi Driver.
  • A couple to William Shakespeare. Queenan drops "the readiness is all" from Hamlet in a scene where he's telling Sullivan to start the police raid. Later Costello slightly botches a quote from Henry IV, Part 2, saying "Heavy lies the crown" (it's actually "Uneasy lies the head that wears a crown").
• Sir Swears-a-Lot: Staff Sergeant Dignam.
• Smug Snake: Sullivan grows increasingly more loathsome throughout the film, climaxing in his confrontation with Costigan on the roof and subsequent elevator ride. Weeping, he begs a clearly disgusted Costigan to shoot him to give him an easy way out. Costigan refuses.
• The Smurfette Principle: Madolyn is the only notable female character.
• Southies: A movie that codified this for the 21st Century.
• Spies In a Van: We see someone from the police force taking pictures of Costello from a white van. Sullivan gives Costello a tip to warn him.
• Spotting the Thread: Had Sullivan not carelessly left Costello's envelope on his desk, Costigan would not have deduced that he's Costello's mole.
• Spy Speak: When someone is communicating with Costello via phone, they always address him as "Mom" or "Dad" to make it seem like they're communicating with their parents. One example is when Fitzy is detained for a traffic violation. Sullivan poses as the lawyer and tells him to call his mom and tell her he won't be home for supper. Fitzy goes along and makes the call, which goes to a house where Mr. French and Costigan are handling some drugs. He says the line, which tells them to clear out the apartment, then set the place on fire.
• Strange Minds Think Alike:
  • The cranberry juice scene.
  • The echo of the "When you're facing a loaded gun, what's the difference?" This is what Costello says in his opening monologue, then Costigan to him in a bar later on.
  • "School's out."
• String Theory: The cops use a wall with pinned photographs of their targets to help keep track of the connections between them.
• Surprisingly Sudden Death: Billy Costigan gets killed instantly with no warning.
• Suspiciously Clean Criminal Record: When Sullivan is up for promotion, Ellerby says to him "You have an immaculate record. Some people don't trust a guy with an immaculate record. I do. I have an immaculate record." (The irony, of course, is that Sullivan is The Mole in the police force.)
• Sympathetic Adulterer: Madolyn is quite warm and nice for someone who cheats on her boyfriend.
• Team Dad: Queenan, especially to Dignam and Costigan. When Costigan had enough of Dignam's abuse and they started brawling on the street, Queenan breaking them up was like a father dealing with his two misbehaving kids.
• Television Geography:
  • Boston's Government Center is portrayed as the Massachusetts State Police headquarters. In actuality, the MSP general headquarters is in the town of Framingham, about twenty miles to the west.
  • Likewise, the Massachusetts state police academy is in New Braintree, a small town outside Worcester, not Boston.
  • An undercover investigation into the Boston mob would probably be conducted by the Boston Police Department, not a state police force. However, there is a BPD city cop undercover among Costello's crew (Delahunt), and it's doubtful Costello limits his criminal activities to the city itself, which might be why the State Police are involved.
  • When arrested by Costigan, Sullivan tells him, "Good luck explaining this to a Suffolk County jury!" Suffolk County has no government or courts of its own, as they have been incorporated into the city of Boston.
• There Are No Therapists: Averted Trope: Billy Costigan must see a therapist as part of his "parole" and to maintain his cover.
• These Gloves Are Made for Killin': Colin Sullivan seems to get away with everything, when he steps into his apartment to find Sean Dignam wearing rubber gloves and booties over his shoes. Sullivan resigns himself to his fate and is shot dead.
• This Is Unforgivable!: How the State Police feels about Queenan's death. They're actively hunting Costello after that, and not even bothering to be subtle with their tails. This is Truth in Television since cops get extra upset when one of their own is attacked, and Costello's gang attacked their chief.
• Three-Volley Flinch: One of the ways we can tell that Sullivan is a hard-hearted sociopath is that he's the only person who doesn't flinch at the sound of the guns at the police funeral.
• Title Drop: Thrice in English, once in Cantonese.
• Trapped Undercover: Both main characters, to a certain degree:
  • Played straight with Sullivan. When things start to go south for Costello, he sets up the mob boss's arrest and uses the raid as an excuse to kill him, then does his best to cover his tracks and act like an upstanding member of the force.
  • Zig-zagged with Costigan. At first, when Captain Queenan is killed and Staff Sergeant Dignam resigns, it appears this trope will be in effect, but he's able to make contact with other officers and pass along enough information to bring down Costello, then extricate himself and report in to headquarters. There's even a secret file on Queenan's computer confirming his identity... which Sullivan promptly deletes when he realizes Costigan can identify him...
• Troubled, but Cute: Costigan, to Madolyn.
• Uncomfortable Elevator Moment: Costigan and Sullivan after they know the truth about each other.
• Undercover Cop Reveal: After Delahunt is killed, the news reveals that he was a cop, but it's ambiguous whether this is true.
• Understatement: Fitzy at the bar after they kill Queenan.
  Fitzy: That cop was tough. We were excessive with the cop.
• Undisclosed Funds: When Billy is hired for the undercover job, Queenan writes a sum on a piece of paper and hands it to him. We never get to see how much he was offered, but we can assume these are the $30,000 "insurance money" Billy later claims to have received for his mother's death.
• Ungrateful Bastard: So how does Sullivan thank the guy who saved him from his captor? By shooting his rescuer in the face, of course.
• Unwitting Instigator of Doom: Ellerby is this thanks to his favoritism of Sullivan. He's the one who puts Sullivan in charge of finding Costello's mole in the police and his suspension of Dignam later in the film prevents Dignam from arriving with Brown to help Costigan arrest Sullivan, leading to several deaths.
• Unperson: With no one from the undercover unit left to vouch for Costigan, Sullivan deletes his service records. This drives Costigan to desperately corner and arrest him, but he ends up dead. Ironically, when he's dead, Sullivan reveals his identity and makes him into a hero anyway.
• The Unreveal: What Costello got Sullivan after he graduated from the Police Academy. The screenplay actually goes out of its way to say we'll never know what it is.
• Very Loosely Based on a True Story:
  • While the film is a remake of Infernal Affairs, Costello was also partially based on real life Irish Mob boss James "Whitey" Bulger who was also working for (and protected by) the FBI. He eventually became one of the FBI's Ten Most Wanted and was finally arrested in June 2011. Strangely enough, Bulger was rumored to have seen the movie when it came out, and apparently liked it.
  • Colin Sullivan is also based loosely on John Connolly, who Bulger used to treat to ice cream as a kid, and grew up to become the FBI agent who regularly tipped Bulger off that that the police were on to him in return for info that brought in lesser criminals who often coincidentally happened to be Bulger's rivals.
• Vigilante Execution: Sorta. Sullivan manages to kill the only people who've discovered that he's Costello's mole and appears set to get away with it without even being charged with a crime, much less convicted, but Sgt. Dignam has other ideas.
• Villainous Breakdown: Frank Costello, and later on, Colin Sullivan at the end.
• Villainous BSoD: Played with when Sullivan discovers that Costello is an informant he leads the police to the gang's location and ultimately kills Costello himself, actions that are undoubtedly "moral," yet he only does these things to close the door on his criminal life and to save his own skin.
• Villain Protagonist: Sullivan.
• Visual Innuendo: During the scene where Madolyn reassures Colin about his attack of impotence, she is holding... a banana.
• Waxing Lyrical: After Costello gives Sullivan his present - for graduating from the academy - he says to him, "No more pencils, no more books."
• White Sheep: Costigan's deceased father was this to the rest of his criminal family. Unlike Costigan's various uncles with their long rap sheets, and his small-time, idiot cousins, Costigan's dad made a meager but honest living as a baggage handler at the airport. Which is not to say that dear old dad lived entirely on the straight and narrow, or that he was incapable of being a force in the criminal underworld if he'd chosen a life of crime, simply that he decided not to be involved in it. Costello notes that in his prime, Costigan Senior would have gone on a rampage and tried to kill Costello and anyone who got between the two men just at the thought of Costello leading his son astray.
• Wicked Cultured: Costello is a fan of opera and references James Joyce, which a young Sullivan immediately gets. The older Sullivan tries to cultivate this with Madolyn, by proving to be very knowledgable about Freud, and more than a stereotypical Irish cop.
• Your Mom: Averted, Dignam sees this line coming and prevents it from being used on him.
  Ellerby: Go fuck yourself.
  Dignam: I'm tired from fucking your wife.
  Ellerby: How's your mother?
  Dignam: Good, she's tired from fucking my father.

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