Film: The Departed

Francis, it's a nation of fucking rats.

The Departed is a 2006 American crime-thriller film and remake of the 2002 Hong Kong crime thriller Infernal Affairs.

The Departed was 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 was nominated for five Academy Awards at the 79th Academy Awards of which it won four; Best Picture for Graham King, Best Director for Martin Scorsese, Best Adapted Screenplay for William Monahan and Best Film Editing for Thelma Schoonmaker. It was the first Best Director win for Scorsese. Mark Wahlberg was also nominated for Best Supporting Actor (he lost to Alan Arkin for Little Miss Sunshine)

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

Meanwhile, 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 Costigan refuses to be intimidated out of dropping out of 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 Sullivan and Costigan attempt to discover the other mole's true identity before being found out.


This film provides examples of:

  • Abandoned Warehouse: 344 Wash is conveniently empty.
  • Academy Award: It was nominated for five Academy Awards: Best Picture, Best Director, Best Supporting Actor, Best Adapted Screenplay and Best Film Editing. It won four of them, only losing Mark Wahlberg's nomination for Best Supporting Actor.
  • Adaptation-Induced Plot Hole: One wonders why Costigan doesn't go to Dignam for help after Queenan is killed. In the original film, the captain was the only one who knew about the operation, leaving the hero completely on his own after his death.
  • Age Cut: Colin Sullivan has one at the beginning to transition from his youth to him in the police academy.
  • Alliterative Name: Madolyn Madden.
  • Animal Motifs: Rats are a common motif. The last shot features a rat scurrying across a balcony with the state house in the background.
  • Anti-Hero: Costigan is mostly a Pragmatic Hero. He participates in some pretty bad shit and is certainly a real Badass.
  • Anyone Can Die: Almost everyone can and will.
  • Artistic License – Law: 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.
  • Asian Speekee Engrish: Costello says, "No tickee, no laundry," to insult some Asian gangsters with the broken English and Chinese laundry stereotypes.
  • Asshole Victim:
    • The police's view on Miles Kennefik, 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. Subverted with Delahunt in that he doesn't count because it is revealed that he kept Costigan's identity as a spy a secret because he himself is also an undercover cop.
    • And at the end, Barrigan and finally, Sullivan himself.
  • Ate His Gun: Mr. French had already been shot and then was trapped in his crashed/burning car, with the State Police closing in. "...fuck it."
  • Ax-Crazy: Frank Costello embodies this trope.
  • 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.
  • 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.
  • Bilingual Bonus: Anyone who can understand Cantonese will get what the Chinese were ranting about, though their accents are off.
    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.
  • Big "Shut Up!": Costigan to Sullivan, punctuating each syllable with a punch to the face.
  • Black and Gray Morality
  • 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.
  • Bookends: 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.
  • 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.
  • California Doubling: New York stands in for Boston in some scenes.
    • In most scenes ... Scorsese wanted to shoot in Boston, but there were issues, and New York offered a tax credit, so they only shot in Boston for a week to use scenery that was identifiably Boston.
    • However, due to the success of the film and the academy awards it earned, a 25% tax credit was created for filmmaking in the Commonwealth of Massachusetts. Subsequent films that take place in Boston, like The Town, have hence been shot on location, and several films that are set elsewhere have been made in Massachusetts.
  • 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 unpredictable for people who have seen the original.
  • Captain Smooth and Sergeant Rough: Dignam is much more coarse and rough when compared to Captain Queenan.
  • Chekhov's Gun: The envelope.
  • 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.
  • 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...
    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 musch difference between the good guys and the bad guys. One can argue that cops like Dignam and Ellerby are little better than Costello. 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. Possibly Queenan.
  • Cruel Mercy: Once he sees the jig is up, Sullivan begs Costigan to kill him. Response: "I am killing you."
  • 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.
  • Deadpan Snarker: Sergeant Dignam.
  • Deathbed Confession: Delahunt is trying to open up to Billy about his true identity but dies during his confession.
  • 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: Arguable. It's possible that after his death, Delahunt's identity as a cop (if he even was one) is intentionally made public in order to take the heat off of Costigan.
  • Destination Defenestration: Queenan is thrown out a window by half a dozen of Costello's thugs.
  • Detective Mole: Sullivan.
  • Dirty Cop: 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. In a way, Costigan is technically one of these given that he is sent to prison on a trumped-up assault charge so that he can have an official criminal record and street cred before infiltrating Costello's crew, given his family's background.
  • Disappeared Dad: One of the major themes of the film.
  • Downer Ending: And what a downer it is, not that anyone expected it to end well. 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.
  • Dragon Their Feet: Reversed and played straight at two different points.
  • The Dragon: Mr. French is Costello's.
  • 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.
  • Embarrassing Old Photo: It's only Sullivan who thinks this way about Madolyn 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: How Costigan and Sullivan react to Madolyn's childhood photograph. It was to highlight the difference in the two characters. Sullivan was more concerned about his career and his 'image' and so he didn'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.
  • 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". 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.
  • 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.
  • Evil-Detecting Dog: A dog shies away from Sullivan.
  • 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..."
  • Feed the Mole: In order to find the rat at SUI, Billy tells Dignam to slip the info about cameras being installed at Costello's place: "Flush it down the pipe, see if it comes out on my end."
  • Fingertip Drug Analysis: Costello tastes the cocaine during the drug deal.
  • Flock of Wolves: The only two named members of Costello's crew who aren't undercover cops or confidential informants are Fitzy and Mr. French. And that's including Costello himself.
  • Foil: All over the place:
    • Costigan and Sullivan are both Southie Irish kids. Costigan comes from a corrupt mob-connected family who goes undercover into the very life he hates for a Redemption Quest, Sullivan is a poor slum kid who becomes an undercover cop who wants to become legitimate.
    • 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: Cops and criminals. The way I see it is when they point a loaded gun on your head, what's the difference?
  • For the Evulz
    Billy Costigan: You're seventy fucking years old. One of these guys is going to pop you. As for running drugs, what the fuck. You don't need the pain in the ass, and they're going to catch you. And you don't need the money.
    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 any more either... but I like it.
  • 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 floor pattern in 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 Harrigan all die.
  • Good Cop/Bad Cop: When Costigan is being interviewed about his application by Queenam and Dignam, Queenam 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.
  • Good People Have Good Sex: Costigan is a love machine. Sullivan, meanwhile, seems to have issues with erectile dysfunction. Guess which one is the hero. Averted by Costello, however, who has an active sex life (even at his old age) despite being a far from exemplary individual.
    • Word of God says that Costigan is actually the father of Madolyn's child.
  • Had to Come to Prison to Be a Crook: Invoked when Costigan gets four months in prison to build up a reputation as a crook to be able 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.
  • 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 an Anti-Heroic version.
  • Hired to Hunt Yourself: Sullivan, looking for a mole within the police department. He Hangs A Lampshade on this while talking to Costello about it.
  • Hollywood Silencer: In the final scene.
  • Hypocrite: Frank told Colin as a kid not to let anyone tell him what to do. Frank's an FBI rat.
    • Sullivan and Costigan calling other characters "rat fucks" is pretty hypocritical.
  • 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.
  • I'll Kill You!: Billy says this to Sullivan in the elevator.
  • If You're So Evil, Eat This Kitten: Billy is constantly being tested by Costello.
  • 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. Then Delahunt turns out to be an undercover BPD cop.
  • The Infiltration: Costigan plays the trope straight when infiltrating the Boston underworld. Sullivan plays The Mole.
  • Instant Death Bullet: Played straight for at least four characters, including major ones.
  • 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: Inverted. 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 inspect 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. He saw to it that Queenan's death, as well as Costigan's (who he didn't even like) were avenged.
  • Karma Houdini: Subverted. At the end it looks like Sullivan is going to get away scot-free. Then Dignam makes sure that can't happen.
  • Kill 'em All: With extreme prejudice.
  • Knee-capping: Sullivan uses this type of Mutilation Interrogation technique on one of the baddies. Apparently it hurts badly if you don't go into shock.
  • Kudzu Plot: They stretch this out into a two-and-a-half hour movie. Hell, it takes 20 minutes just to get to the title card!
  • Large Ham: Frank Costello.
  • 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.
  • Lying to the Perp: During the talk with cousin Sean on the balcony, Costigan is asked to tell if he is a cop, which he denies.
  • Love Triangle: Between Madolyn, Sullivan and Billy. Added for Rule of Drama, there was no such thing in the original.
  • Male Frontal Nudity: Invoked: Costello whips out a fake penis in a pornographic movie theater at one point during a covert meeting with Sullivan.
  • Mexican Standoff: Between Costigan, Sullivan and Brown during the Rooftop Confrontation.
  • "Mister Sandman" Sequence
  • 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.
  • My Card: Madolyn hands her card to Sullivan in their Meet Cute scene at the elevator.
  • 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.
  • 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 he's The Mole for an FBI and has dirt on him that can sabotage his future, so he decides to go Kill 'em All on his 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.
  • One Steve Limit: Averted. There are two characters with the first name "Sean": Dignam, and Costigan's cousin.
  • 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.
    • 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.
    • 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 Password Is Always Swordfish: Costigan reveals that the password for his file in the police database is his full name (including spaces). Sullivan can only shake his head.
  • 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".
  • 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: We see Billy getting in shape while being 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.
  • 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 late father, his late uncle, or his cousins.
  • Right Hand Versus Left Hand: What the movie amounts to. The Massachussets 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 another Mole, only from the Boston Police Department. Essentially a massive Gambit Pileup between city, state, and national police who fail to collaborate or trust each other.
  • 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.
  • Self Offense: Sullivan stabs some random restaurant worker in the chest, believing him to be Costigan.
  • Shout-Out: The scene in the graveyard has significant visual parallels with a scene in The Third Man.
  • 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 to Shakespeare: "Readiness is all." Lampshaded by Dignam.
  • 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.
  • Southies
  • 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.
  • 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."
  • Surprisingly Sudden Death: Billy Costigan gets killed instantly with no warning.
  • 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 Framingham.
    • Likewise, the Massachusetts state police academy is in East 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 BDP city cop undercover among Costello's crew, and its doubtful he limits his criminal activities to the city itself, which might be why the State Police is 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.
  • 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.
  • Title Drop: Thrice in English, once in Cantonese.
  • Troubled, but Cute: Costigan, to Madolyn.
  • 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.
  • Uncomfortable Elevator Moment: Costigan and Sullivan after they know the truth about each other.
  • Undercover Cop Reveal: Arguable, by Delahunt during his final moments.
  • 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.
  • Unperson: With no one from the undercover unit left to vouch for Costigan, Sullivan deletes his service records.
  • 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.
  • Villain Protagonist: Sullivan.
  • 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.
  • Whole Plot Reference: To Gangs of New York: Leonardo DiCaprio plays an Irish guy with a Mob family history who infiltrates a gang in an east coast metropolis in order to gain the trust of the bigoted, extremely hammy mob boss - a lot of Irishisms, dirty cops and a love triangle ensue. Both are directed by Martin Scorsese.
  • Wicked Cultured: Costello is a fan of opera.
  • 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.