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Film / The Town

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Left to Right: Claire, Frawley, Doug, Jem and Kris

"There are over 300 bank robberies in Boston every year. And a one-square-mile neighborhood in Boston, called Charlestown, has produced more bank and armored car robbers than anywhere in the U.S."

The Town (2010) is a heist film, based on Chuck Hogan's 2004 novel Prince of Thieves, that follows a team of bank robbers in the Boston neighborhood of Charlestown and the law enforcement personnel attempting to stop them.

Doug MacRay (Ben Affleck) is not cut from the same cloth as his fellow thieves. Unlike them, Doug had a chance at success, a chance to escape following in his father's criminal footsteps. Instead, he has become the leader of a crew of ruthless bank robbers, who pride themselves on taking what they want and getting out clean: himself, James "Jem" Coughlin (Jeremy Renner), Desmond "Des" Elden (Owen Burke) and Albert "Gloansy" Maglone (Slaine). The only family Doug has are his partners in crime, especially Jem, who, despite his hair-trigger temper, is the closest thing Doug ever had to a brother.

However, everything changes when Coughlin takes a bank manager named Claire Keesey (Rebecca Hall) hostage during one robbery. When they discover she lives a few short blocks away from them, Coughlin gets nervous and wants to check out what she might have seen. Knowing what Coughlin is capable of, Doug seeks out Claire and starts a romantic relationship with her to keep his friend at bay. Claire has no idea the "charming stranger" is one of the men who terrorized her only days before.

As his relationship with Claire grows, Doug also wants out of the lifestyle and the town. But with the Feds, led by FBI Special Agent Adam Frawley (Jon Hamm), closing in, and James questioning his loyalty, Doug realizes that getting out will not be easy. Worse yet, his longtime associate and mob contact Fergie "The Florist" Colm (Pete Postlethwaite) may put Claire in the line of fire. Any choices he once had have boiled down to one: betray his friends or lose the woman he loves, concluding with an epic robbery of Fenway Park.

The film was directed by Affleck, who also plays the lead character. The film opened in theaters in the United States on September 17, 2010 to rave reviews, with Rotten Tomatoes giving it a "Certified Fresh" rating with 94% positive critical reviews. In addition, the film opened at number one at the U.S. box office with more than $23 million. It restored Ben Affleck's credibility as a leading actor, and also cemented his abilities as a director, proving that Gone Baby Gone was not a fluke.

This film contains examples of:

  • Adaptation Distillation: The film removes several elements that were present in the book (most notably Doug's struggle with alcoholism outside of a Continuity Nod in which he attends an Alcoholics Anonymous meeting and drinks juice while the rest of his friends are getting drunk) and changes the ending (which involved Doug being shot by one of Fergie's goons and dying in Claire's arms when Frawley arrives; though this ending was still filmed and available on the extended edition Bluray).
  • Adaptation Title Change: The Town is based on the novel Prince of Thieves.
  • And I'm the Queen of Sheba: When Frawley introduces himself to Krista as an FBI agent, her response is to laugh and say "So am I!".
  • Arc Words: "I'll see you again. On this side or the other."
  • Awful Truth: Two of them, in fact. The more obvious one is that Doug was the bank robber, but later we learn the truth about Doug's mother.
  • Badass Boast: Frawley's entire speech to Doug while he was in custody.
  • Bavarian Fire Drill: The dialogue when Doug and Jem are entering the Fenway Park vault disguised as cops.
    Doug: Who called 911?
    Jem: Did you guys call 911?
    First Security Guard: No one from here called.
    Young Security Guard: No we didn't uh... it wasn't us.
    Doug: Who dialed a 911 call?
    Jem: It's a robbery guys, come on!
    Young Security Guard: You said a robbery?
    Doug: Yeah. A call sayin' you're being held up.
    Young Security Guard: Oh, let... let me call Mike.
    Doug: We just walked past Mike! He let us in!
    Jem: Hey, look guys, we got a distress call. All right. So, who made the call?
    First Security Guard: Nobody called from here.
    Jem: [looks at Doug, bewildered] So... no one called. What are we doing here?
    Young Security Guard: Hold on. Where's Mike?
    Doug: I just told you where Mike was!
    Young Security Guard: You boys see all right? With the uh... [nods to the dark sunglasses that both Doug and Jem are wearing]
    Doug: Huh? Listen, you fuckin' smart ass!
    Jem: For our safety, for everyone's safety here, we need to see your ID's. All right?
  • Bank Robbery: The opening sequence.
  • Beat: When changing from the Jeep SUV to the stationwagon, Doug and his crew stop when they notice a police officer sitting in his cruiser across the street, looking at them. Both sides just stare at each other for a moment, with the cop clearly thinking "They're four guys with automatics. I have a tiny pistol. I shoot, I lose," while Doug and the others are hesitating on whether to shoot him, and risk the wrath of the Boston Police Department. The cop thinks better of it considering the odds and simply looks away, allowing the robbers to flee.
  • Beauty Inversion: Krista Coughlin, played by Blake Lively, who is often seen disheveled and ratty for most of the movie (and often seen with pimples, cuts or bruises). Which is justified given that she's supposed to be a drug mule for Fergie, in sharp contrast to Rebecca Hall's appearance as Claire.
  • Best Friend: James/Jem to Doug. When Doug asks Jem for a potentially dangerous favor that they'd never talk about again, the only thing Jem asks is whose car they'll be taking for it.
  • Best Friends-in-Law: Doug has an on-off relationship with his best friend Jem's sister Krista. Jem is actually really enthusiastic about their relationship, as it means that he and Doug are practically family. However, it's a pretty rocky one and Doug dashes Jem's hopes that there's any future in it since he plans to leave for Florida and he's in love with Claire not Krista.
  • Betty and Veronica: Played with. Doug has two 'love interests' in the film. Krista the trashy addict has the Veronica personality but the Betty traits of knowing Doug his whole life and being his best friend's sister. The wholesome Claire is a Betty personality but is from out of town and functions as something of a Morality Pet.
  • Big Bad: Fergie "The Florist" Colm.
  • Bittersweet Ending: All the members of crew die except for Doug. Jem dies from Suicide by Cop to avoid going to prison. Doug leaves for Florida, but leaves a duffel bag full of money for Claire to find in the garden she tends. At the end, we see him living alone in a house in a Florida bayou, explaining in voiceover that he'll see Claire again someday.
  • Brand X: The cable company Vericom is clearly meant to be Verizon. In fact, it would've been Verizon that Des worked at until right before filming began.
  • Break the Cutie: Claire.
  • Brief Accent Imitation: At one point while interrogating Doug, Frawley mimics Doug's working-class Boston accent.
  • Bulletproof Vest: Doug takes most of a magazine from Fergie at near-point blank range and lives. Whether this is played straight or exaggerated is up to the viewer. Though he is mortally wounded in the alternate ending where he dies.
    • When Doug is grabbed by the overzealous guard during the armored car stickup in the North End midway through, Jem fires a submachine gun at them. Doug seems to survive it quite well again. So does the guard, although he's clearly wounded.
  • Casting Gag: Slaine plays Gloansy, and the climax takes place at Fenway Park, where Slaine worked in his teenage years at a concession stand. He reportedly called going back to the place to shoot the robbery sequence "surreal".
  • Category Traitor: Dino is viewed this way by Doug, having also grown up in Charlestown, only he joined the police force, and used his knowledge of the neighborhood to throw Charlestown criminals in jail.
  • Chance Meeting Between Antagonists: After the armored car robbery, and the very tense police pursuit in the North End, the gang have managed to escape across the Charlestown Bridge before the cops can block it off and are switching cars... only to, in the midst of switching cars for the second time, stop in their tracks because there's a police officer sitting in his car directly across the street, watching them. After a few seconds of locking eyes, the cop turns his head away, deciding it's better to just let them go.
  • Chase Scene: A police chase through the North End's narrow streets.
  • Chekhov's Gun: Claire at one point tells Doug how her brother died on a sunny day; she's later able to use this phrase as a code to warn him to stay away from her apartment when the FBI sets a trap for him there.
  • Chekhov's Gunman: Early in the movie, Doug and Coughlin beat up a guy named Alex Colazzo for harassing Claire. If you watch the Ultimate Collectors' Edition DVD/Blu-ray combo pack, which has the extended version featuring a second alternate ending (no, not the one where Doug dies in Claire's apartment) that makes the movie end all too similarly to The Departed, Alex reappears to confront Doug and then shoots him.
  • Clothing Damage: Doug cut off of a sleeve from the Claire's jacket to make a blindfold to use on her when they abducted her. After that, her jacket is completely gone.
  • Cluster F-Bomb: The movie is very liberal with F-word. But then, the movie is set in Boston.
  • Cowboy Cop: Subverted. Frawley may seem like a very dark take on this, but nothing he does violates the law or standard police protocol. He's simply ruthlessly efficient and willing to anything within the law to do his job.
  • Curb-Stomp Battle: Towards the film’s climax, an FBI SWAT unit is dispatched to deal with the robbers. Dez is almost immediately killed by an FBI sniper and Gloansy is shot multiple times before crashing the getaway ambulance into a police van and succumbing to his injuries. Jem manages to get away but is tailed by Frawley, whom he fires at but eventually runs out of ammo. Not wanting to go back to prison, Jem comes out of cover with his guns drawn and is killed by an FBI marksman within a second. This film serves as a reminder that you don’t want to get on an FBI SWAT team’s bad side.
  • Dead Foot Leadfoot: When the Atlantic armoured car driver attempts to escape from Fenway Park, Doug jams his automatic rifle through the gun port and blazes away. The driver is killed and the armoured car keeps driving and crashes into the police lines.
  • Demoted to Extra: Dez, who is The Smart Guy in the book and the Hufflepuff House of Doug's crew in the movie.
  • Did Not Die That Way: Doug's mother turns out to have killed herself, as opposed to the story that his father tells him.
  • Did Not Get the Girl: Because he was the criminal who traumatized her, that's why.
  • The Dragon: Fergie's associate Rusty, though Doug effortlessly dispatches him at the end.
  • Drives Like Crazy: Gloansy's skill is as the getaway driver. However, his driving during the police chase in the North End counts as he drives through narrow one lane streets at speeds in excess of 60 mph, and causes multiple pileups to occur while trying to evade the police. And then after they manage to get the police cars chasing them disabled and change cars, he is seen driving at over 60 mph against oncoming traffic to get to the Charlestown Bridge before the police can block it. When they get to the bridge and race across it untouched, he turns to the others and quips, "Now that's how you drive a fucking car!" as they watch the police screech to a stop behind them.
  • The Dulcinea Effect: Even though Doug has only known Claire for a couple of weeks, he is still willing to take part in a major heist so that Fergie and his henchman won't kill her as an intimidation tactic.
  • Flashback: A killing which happened long ago and which Doug and Jem talk about is shown.
  • Flashback Effects: The killing flashback is black and white.
  • Foreshadowing: When Doug talks to Krista in the bar, the song on the jukebox is "Whatcha Say" by Jason Derulo, about a man who lied to his girlfriend and whose world falls apart when she finds out. Guess what happens when Claire is told by Frawley that Doug is the robber who kidnapped her and released her unharmed.
    • When Doug tells Fergie that he will kill him and his bodyguard in his own flower shop ...if anything happens to Claire, that is.
  • Free Wheel: During the police chase, the gang's minivan loses its left front hubcap while trading paint with a police car.
  • Gangsterland: If the statistic in the page quote is to be believed (it isn't), Boston certainly fits. The actual FBI crime statistics on bank robberies in Boston are definitely much lower than 300 bank robberies a year. 300 is actually the number of bank robberies throughout the entire Commonwealth of Massachusetts in a year, and that includes not just the ones with guns and gunplay, but also the "clerk stealing from the till" and "man with extortion note" jobs.
  • Genre Savvy / Pop-Cultural Osmosis: Invoked. When talking to Claire, Doug lies that his knowledge of witness protection procedures comes from TV shows like CSI, and not from, say, all of the times he was arrested for petty crimes.
  • Gilligan Cut: When Doug asks Claire if he can get her a drink. He says "What's the worst that could happen?" Cuts to Frawley and Dino raiding a drug dealer's apartment.
  • Good Is Not Nice: Agent Frawley, to the point that at times he's no better than the protagonist himself. He's also a Combat Pragmatist and has no problem pulling dirty tricks (though still legal) to bring the gang down.
  • Groin Attack: Doug kills Fergie at the end by shooting him in his nuts. We don't see it though, since the camera cuts to a black screen when Doug pulls the trigger.
  • Hero Antagonist: The FBI agents. Frawley himself is an Anti-Hero Antagonist.
  • Hold the Line: During the climax, Gloansy decides to distract the cops by driving away in the ambulance while Doug and Jem escape with the money wearing their police disguises. He gets killed.
  • Hollywood Law: Although averting Lemming Cops, any police department would likely terminate their pursuit of Doug, Coughlin and Gloansy after the failed attempt to wall them in with a PIT maneuver. This is because the typical rules of pursuit are to not attempt to to stop the fleeing vehicle if doing so risks injury or death to the cops or bystanders, a chance that is made more likely when it's in the narrow one-way streets of the North End, and in the chase, three police cars are disabled by getting shot up, and a fourth is forced off course and t-boned by another motorist.
  • Honor Before Reason: When Doug's father was arrested for taking part in a robbery and killing two guards, he was offered a reduced sentence if he named his co-conspirators. He refused to rat on his friends and received a life sentence. Doug's friends consider him a hero for the act.
  • Hufflepuff House: Desmond Elden, who's got a developed backstory as The Smart Guy in the original novel but is practically a non-entity in the film (Gloansy's characterization is also substantially reduced, but at least he gets a Funny Moment in the interrogation room (the "You weren't supposed to get out of the truck. You got him, but who got me? [beat] Courier, get on the ground before I pop your fucking teeth out!" line).
  • Imperial Stormtrooper Marksmanship Academy: Played realistically straight, during several shootouts neither the robbers nor law enforcement seem able to hit anyone. Though this could be because they’ve been firing full auto for extended periods of time, thus reducing accuracy.
  • Impersonating an Officer: Doug and Coughlin go one step farther and actually wear police officer uniforms to rob the cash room at Fenway Park. While their attempt to escape while dressed as paramedics fails due to the FBI SWAT team cornering them, after Gloansy and Des get killed, Doug and Coughlin slip back into the cop uniforms to blend in with a group of real BPD officers that have just showed up. Too bad it doesn't work out for Coughlin when Frawley catches him while he tries to flee with the money satchel on his shoulder.
  • Inspector Javert: Agent Frawley really wants to catch Doug's gang.
  • Inside Job: Subverted, then played straight. The robbery at Claire's bank does not involve an employee accomplice but the cops think that there might have been one. When Claire quits her job, it raises red flags and when her relationship with Doug is discovered, she is accused of being that accomplice even though the audience knows she is innocent. The later robbery at Fenway Park involves an inside man, a Fenway employee who owes Fergie a lot of money and has been promised that his debts will be wiped clean if he provides Doug with access to the money room.
  • The Irish Mob: Fergus 'Fergie' Colm. Doug's gang, though Irish-American crooks, probably don't count, being 'merely' freelance bank robbers.
  • Ironic Echo:
  • I Surrender, Suckers: Coughlin with his Suicide by Cop. Surrounded by a firing squad of cops, he announces that he's giving himself up, then leaps from cover with emptied TEC-9s. The police officers don't know that his guns aren't loaded, though, and riddle him with bullets.
  • Jerkass: While he may have noble intentions, the way FBI Special Agent Adam Frawley goes about his job is a bit over-the-top. His conversations with Krista, where he casually lays out her past in cheerful detail while simultaneously intimidating her, and casually mentions that her daughter is being transferred to Social Services in a later conversation, exemplifies his behavior.
  • Jitter Cam: Done several times during the three action set pieces-the bank robbery, the North End armored car robbery and police chase, and Fenway Park shootout-to make the action much more intense.
  • Karma Houdini: Subverted. Doug escapes and makes it to Florida, but the rest of the crew is dead, and he's alone. Averted if you watch either of the alternate endings on the extended edition, where Doug dies.
  • Know When to Fold 'Em:
    • The lone patrolman who sees the gang changing cars stares at them for a few seconds before pointedly turning his head and letting them get away. It likely saved his life.
    • When the Fenway Park robbery goes to hell, Doug is smart enough to leave the money behind so he can better blend in and get away from the cops. Jem takes a money satchel with him, gets spotted and gets shot dead.
    • With the FBI on his tail Doug does not stick around Boston or try to meet up with Claire again and instead flees to Florida hoping that Claire might join him there somewhere.
  • Lemming Cops: Averted in the North End car chase. While multiple police cars are totaled either by getting shot up or through pileups caused by tight turns or being forced off course, they're completely working within the bounds of how an actual police pursuit might unfold.
  • Losing a Shoe in the Struggle / Barefoot Captives: Claire is explicitly told to remove her shoes by Jem for whatever reason during the opening bank robbery; since she isn't wearing any tights or stockings, this leaves her in bare feet for the rest of the robbery and her subsequent abduction.
  • Malevolent Masked Men: Each of the three robberies has the gang using a different sets of masks, no less. The opening bank robbery involves them wearing skeleton masks, with black jumpsuits, pants, and shoes. The armored car robbery midway through the movie has the gang use rubber nun masks (with veils included). They use a combination of police officer uniforms, peaked caps, handkerchiefs, and sunglasses in the Fenway Park robbery, with paramedic uniforms immediately afterwards.
  • Manipulative Bastard: Fergie fits this trope to a T.
  • Menacing Mask: In the first heist, the robbers wear hoods and rubber dark skull masks that feature discolored teeth. Later in the film, they wear matching nun costumes with rubber masks in the likeness of wrinkled women.
  • Metaphorically True: When asked by Claire about his father, Doug says that he "finally made it out to the suburbs" which is true, technically, only he left out the fact that where his part of "the suburbs" is actually the Cedar Junction state prison in Walpole.

  • Missing Mom: Doug's mother, Doris, left him at a young age. He searched all over town for her, but never found her, and assumes she went to Florida. Later on, Fergie reveals to Doug that he hooked Doris on drugs, which caused her to overdose, and, eventually, kill herself.
  • Noble Demon: Doug. For being a career criminal he's a very kind and likable guy, and unlike most of the other criminals in the movie, he tries not to hurt anyone during his bank robberies, other than maybe the courier during the armored car robbery halfway through the movie.
  • Nuns Are Spooky: Doug and his men run the second heist wearing rubber nun masks. Look no further than this page, and happy nightmares.
    • A fun fact is that the script states the robbery originally had them wearing reverse facial masks, which meant you couldn't tell whether they were walking towards you or away from you. They probably changed it because that would have been way too creepy for the viewers.
  • Oh, Crap!:
    • The look on that little boy's face as he catches a glimpse of Doug in the back of the van, wearing a nun mask and carrying an assault rifle, in slo-motion, just literally seconds before shit is about to go down a half-block away.
    • Doug, Jem, and Gloansy's reaction after they complete the robbery. They've loaded the money, and are driving away, they round a corner...and there's suddenly a police car chasing them.
    Doug: Shit.
    Jem: Fuck. They must have been around the corner! [Gloansy hits the gas pedal]
    • The look on Fergie's face when he realizes that Doug is about to kill him by blowing his balls off.
  • One Last Job: Fenway Park.
  • One Last Smoke: Not quite a smoke, but before he provokes the police into shooting him, Jem enjoys the last of a discarded beverage he sees on the ground.
  • Only Bad Guys Call Their Lawyers: Agent Frawley claims this to be true when a woman they brought in for questioning (who is unaware her latest boyfriend is a bank robber) asks him whether or not she should have a lawyer present. Though he prefaces it by saying "it isn't a very civil libertarian thing" for him to say, as he's a cop. When she's later implicated in her boyfriend's crimes, he says that this time she really will need a lawyer.
  • Ooh, Me Accent's Slipping:
    • Claire is played by English actress Rebecca Hall, and her accent subtlely slips throughout the movie. One example is in the scene where Doug and Claire are on a date and run into Jem. The line "So you haven't been telling all your friends about me," is clearly said in Hall's native British accent.
    • Pete Postlethwaite's Irish accent slips in a few scenes as well.
  • Pet the Dog: We figure that Doug's the 'good' criminal when, while Coughlin's yelling at the terrified Claire to hurry up when she keeps flubbing the lock to the bank vault, he puts his hand over hers and gently tells her to breathe deeply and take her time.
    • Jem himself gets a moment late in the movie when he reveals that a guy he murdered in a cemetery at age 18 (for which, according to the police file seen in Frawley's briefing, he served nine years for manslaughter on the grounds that "he didn't like the kid") had been planning on killing Doug, and Jem intercepted him en route.
    • The look on Frawley's face when Coughlin decides to make the cops kill him looks almost mournful, showing that while he would have stopped at nothing to arrest a bad guy, he wanted to take Coughlin alive.
  • Paper-Thin Disguise: Played straight with the way Doug and Jem use their cop disguises to escape Fenway Park as the police move in. By using the disguises, they blend in with the real Boston Police Department officers. "Officer Coughlin" however gives himself away to Frawley by carrying his money bag with him, walking away, and also shooting at Frawley when Frawley calls him by name (although what would happen if he hadn't reacted by shooting when his real name was called is not clear). While "Officer McRay" manages to escape because he behaves like every other cop at the scene-he draws a pistol and holds it in the same way the real cops are holding their weapons, as if he's just arrived. Plus Doug is not carrying a satchel full of money, so he doesn't stand out.
  • Past in the Rear-View Mirror: Doug. "Let me put it to you this way, I'm putting this whole fucking town in my rear view."
  • Pop the Tires: Frawley uses a shotgun to blast out the rear tyre of the ambulance fleeing the ballpark; causing it to flip and crash.
  • Pretty Little Headshots: Every member of Doug's gang goes down like this.
  • Precision F-Strike: Gloansy's "Now THAT's how you drive a fucking car!" as they race across the Charlestown Bridge untouched after narrowly avoiding a police roadblock, after some pretty badass driving.
  • Product Placement: Plenty abound around Fenway Park. When Claire tells Doug about Jem's tattoo, they're in a Dunkin' Donuts. During the bank robbery, the robbers repeatedly call cell phones "Blackberries."
  • Pseudo-Crisis: Inverted. After their second robbery, the team races across the Charlestown Bridge untouched (leading out of the North End across the river to Charlestown) before the police can either set up a roadblock or open the drawbridge. When they get across and are sure no one's followed them, they jump out of their getaway SUV and prepare to torch it...and then they turn around and see a cop sitting in his car across the street, staring in wide-eyed surprise at them and their automatics. After a few moments staring at each other, the cop turns his head the other way and they quickly drive off.
  • Psycho for Hire: Jem seriously shows signs of this.
  • Reality Is Unrealistic: There were a few complaints about the scene where the lone cop turns his head away after staring at the four armed robbers for a few seconds, but Affleck based it on an actual event that happened to a bank robber he interviewed in prison. And considering that Doug and his gang have automatic weapons, and the cop probably only has a pistol at best, it probably saved the cop's life, and it might have saved the lives of the nearby construction workers.
  • Red Oni, Blue Oni: Jem (red) and Doug (blue).
  • Re-Cut:
    • There exist four versions of the movie. The original cut was 4 hours long. After realizing that the film would never appeal to wide audiences, Ben Affleck cut the film down to the still lengthy 2 hours, 50 minutes in 3 days. The studio and producers loved it, but they wanted the film to be no longer than 2 hours, 10 minutes. Eventually, Affleck cut the film down to 2 hours, 8 minutes.
    • When the movie was released to DVD and Blu-ray, two versions were initially available: the original 128 minute theatrical cut, and the 145 minute Extended Cut, available on the Blu-ray. The Extended Cut adds 17 minutes of new and alternate footage to the movie. Most of the new footage revolves around Doug and Claire's love story. This is important to the plot (and avoids a dreaded Romantic Plot Tumor) since it further explores the reasons why Doug is trying to leave his former life behind; also, it offers an inside view on victims of bank robberies (and not just the bank robbers or the police who chase them). The problem-which is not at all Affleck's (neither as a director nor as an actor), Rebecca Hall's or the plot's fault-was that there had been too many love stories already. As the Doug and Claire love story is the part of the plot that was shortened the most for the Theatrical Cut, most of the additional scenes from the Extended Cut develop Doug and Claire's relationship a little further. It's important that Claire talks to Doug about the bank robbers from Charlestown, or about her injured colleague. It is also important that the two gangsters (who were badly injured by Doug) get a chance to speak. However, these are the scenes that slow the pacing down a little bit. Another scene added in the extended cut is a subplot about the gang pulling a prank on the FBI by tricking Frawley into thinking the gang will use a Vericom truck to attack an armored car in a strip mall parking lot; subsequently, they fall for the trick and only bust a poor decoy who was planted there).
    • Affleck has stated that while the Theatrical Cut is a close adaptation of the novel Prince of Thieves, the Extended Cut is more true to the book.
  • Red Herring:
    • Even though the scene where Jem finds Doug with Claire at a restaurant is based around Doug being scared shitless because Claire might see Jem's neck tattoo, which she saw during their heist on her bank, it never comes up again, nor does it affect the heroes in any way afterwards. Neither does Claire's angst over not telling the FBI about the tattoo in the first place, although it does Foreshadow that she will lie to the FBI in the end.
    • In the extended cut, the gang play a prank on the FBI by tricking them into planting a tracking device on Dez's Vericom cable van and having a decoy take it home for the weekend. A few days later, Frawley and his team are monitoring the truck in a strip mall parking lot. Conveniently, there's a boosted Jeep Grand Cherokee a few spaces away. By pure chance, a money transporter then shows up, so the police pile out of their cars and storm the Vericom van, only finding the poor decoy.
  • Resignations Not Accepted: Fergie doesn't take it well when Doug announces that he no longer wishes to work for him, threatening to go after Claire. It's also revealed Doug's father tried to do the same thing to Fergie years ago, leading to Doug's mother's death.
  • Say Your Prayers: When they are preparing to ambush the armored car, Gloansy says this to Doug and Jem as a code signal for them to put on their rubber nun masks.
  • Shout-Out: In the extended cut, a scene happens where Doug is watching the drive-in movie theater shootout from Heat. Heat was the source movie that The Town took heavy influence from.
  • Spanner in the Works: Surprisingly, it's not Claire but Krista who sells the protagonists out at the end.
  • Shell-Shock Silence: Used to great effect during the Fenway Park shootout, when the SWAT team throws flashbang grenades into the parking garage.
  • Shown Their Work:
    • The police chase in the North End features a very accurate portrayal of a PIT maneuver: the police car pulls up alongside Gloansy's minivan, then steers directly into the rear end of the car, causing it to spin to a stop.
    • The armored car attack and chase also took some basis from a notorious thwarted armed bank robbery in Harvard Square (location of Claire's bank) in 1995 that led to an intense shootout between an armed guard and wounded two of the would-be robbers seriously.
  • Slow-Motion Pass-By: Just after Doug and Jem have put on their rubber nun masks, which also have veils, before the armored car ambush, Doug-sitting in the backseat-looks out his window. The camera promptly overcranks as he locks glances with a young boy on the sidewalk. The boy has a horrified look on his face as he sees Doug ride by, submachine gun drawn. The action then ramps back up to regular speed as the van speeds up to the street corner, screeches to a halt on the corner, and the robbery unfolds.
  • Steel Eardrums:
    • Averted in the Fenway Park shootout, since Doug tells the others to cover their ears after the SWAT team throws flashbang grenades through a vent. Only Dez fails to cover his ears, is deafened, and is then shot in the head by a SWAT officer.
    • During the police chase following the armored car robbery, at one point the police cars stop them with a PIT maneuver. An officer is ordering them to surrender on his car megaphone. Coughlin, in the backseat, responds by raising a submachine gun and opening fire through the front windshield to riddle the police car with bullets. Gloansy, Coughin and Doug should all have temporary hearing loss because of the confined space of the car, but they don't suffer any hearing loss for the remainder of the car chase.
  • Southies
  • Start My Own: Doug's father tried this. It didn't work out.
  • Suicide by Cop: Jem's final fate. Cornered by Frawley and the BPD, he can either go to prison or get shot. He's out of ammo. So he aims his empty guns and the cops do exactly what they've been trained to do when someone points any weapon at them, and empty their guns into him before they even knew that he's out.
  • Trojan Ambulance: Doug and Jem enter Fenway Park disguised as Boston police officers, steal $3.5 million in gate cash, and prepare to escape in an ambulance, dressed as paramedics.
  • Unlimited Wardrobe: Not only does the gang have different outfits and masks for their different heists (as seen throughout the film), but it's revealed that the gang has several different disguises and uniforms for remaining inconspicuous, including police, hospital and MBTA bus driver uniforms. Admittedly Doug does tell Claire he has family who work with the 'T', which explains where he gets the bus driver uniform.
  • Villain Protagonist: Doug.
  • What the Hell, Hero?: Claire pulls one on Doug when Frawley tells her Doug's not only a bank robber, but the one who kidnapped her and gave her PTSD.