"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."
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 became the leader of a crew of ruthless bank robbers, who pride themselves on taking what they want and getting out clean. The only family Doug has are his partners in crime, especially James "Jem" Coughlin (Jeremy Renner), who, despite his hair-trigger temper, is the closest thing Doug ever had to a brother.
However, everything changes when Jem takes a bank manager named Claire Keesey (Rebecca Hall) hostage during a robbery. When they discover she lives a few short blocks away from them, Jem gets nervous and wants to check out what she might have seen. Knowing what James is capable of, Doug seeks out Claire and starts a 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.
The film (an adaptation of Chuck Hogan's book Prince Of Thieves) 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 95% positive critical reviews. In addition, the film opened at number one at the U.S. box office with more than $23 million.
- Adaptation Distillation: The film removes several elements that were present in the book (most notably Doug's struggle with alcoholism) and changes the ending (which involved Doug being shot by one of Fergie's goons and dying in Claire's arms when Frawley arrives).
- The movie does show Doug attending an Alcoholics Anonymous meeting, having to drink juice while the rest of his friends get drunk, and he does mention missing his use of alcohol and Oxycontin, though. Except that this is also a case of Actor Shared Background. Ben Affleck is also a recovering alcoholic.
- 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.
- Badass Grandpa: The villainous version thereof. Fergie the Florist is in his sixties at the very least, but still has a very tight grip over The Irish Mob.
- Bank Robbery: Sure enough.
- Beat: When the robbers are wearing nun masks and changing from the first to the second switch car, they 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 torn between doing his job or fleeing with his life, and the robbers hesitating on whether to open fire first. 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 during the film (and often seen with pimples, cuts or bruises). Sharp contrast to Rebecca Hall's appearance as Claire.
- Big Bad: Fergie "The Florist" Colm.
- Bittersweet Ending: All the members of crew die except for Doug. Jem commits 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.
- Brief Accent Imitation: At one point while interrogating Doug, agent Frawley puts on Doug's working-class Boston accent.
- Bulletproof Vest: Doug takes an entire magazine from Fergie at near-point blank range and lives. Whether this is played straight or exaggerated is up to the viewer.
- Watch closely, a few of the bullets miss.
- 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.
- Cowboy Cop: Subverted; though Agent Frawley at times comes off this way nothing he does violates the law or standard police protocol. He's simply ruthlessly efficient and willing to do whatever's allowed to do his job.
- Death by Cameo: Victor Garber appears for 30 seconds in the opening scene as a bank manager who is severely beaten (although not killed) by James during the opening robbery. However, in the extended version of the film, there is a scene where Doug and Claire visit him at the hospital.
- Did Not Get the Girl: Because he was the criminal who traumatized her, that's why.
- The Dragon: Fergie's associate, though Doug effortlessly dispatches him at the end.
- 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.
- From a Certain Point of View: When asked 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 he is in "the suburbs" is actually a prison in Walpole.
- Gangsterland: If the statistic in the page quote is to be believed (it isn't), Boston certainly fits.
- Genre Savvy/Popcultural Osmosis: Invoked. When talking to Claire, Doug lies that his knowledge of witness defense procedures comes from TV shows like CSI.
- 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 hideout.
- Hero Antagonist: Frawley and the other FBI agents.
- Hooker with a Heart of Gold: Subverted with Krista, who is just as desperate and unbalanced as her clients.
- The Irish Mob: 'Fergie' Colm. MacRay and his gang, though Irish-American crooks, probably don't count being 'merely' freelance bank robbers.
- Ironic Echo: "Go fuck yourself."
- I Surrender, Suckers: Deconstructed, as Jem is out of bullets and intentionally uses the ploy to commit Suicide by Cop.
- While he has 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 and intimidates her at the same time, and casually mentions that her daughter is being transferred to Social Services in a later conversation, exemplifies his behavior.
- Fergie goes above and beyond this trope, edging into Complete Monster territory.
- Karma Houdini: Subverted. Doug escapes and makes it to Florida, but the rest of the crew is dead, and he's alone.
- Knight Templar: Agent Frawley will resort to some incredibly nasty means to do his job.
- Malevolent Masked Men: Using different sets of masks, no less.
- Manipulative Bastard: Fergie fits this trope to a T.
- Missing Mom: Doug's mother, Doris, left him at a young age. He searched all over town for her, but never found out where she was. 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.
- Nuns Are Spooky: Doug and his men run their second heist wearing rubber nun masks. Look no further than this page, and happy nightmares.
- 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, as the robbers' van passes them right before the second robbery.
- One-Scene Wonder: Chris Cooper as Doug's father, Stephen MacRay. Also, Pete Postlethwaite is on screen for hardly more than 5 minutes, but makes the most of every moment in an intense, genuinely frightening performance as Fergie the Florist.
- One Last Job: Fenway Park.
- One Last Smoke: Not quite a smoke, but before he lets the police kill him, Jem enjoys the last of a discarded McDonald's Coke he sees on the ground.
- Only Bad Guys Call Their Lawyers: Stated as true by Agent Frawley. Semi-lampshaded in that he prefaces it with saying "it isn't a very civil libertarian thing" for him (a cop) to say.
- Ooh, Me Accent's Slipping: Claire is played by English actress Rebecca Hall, and her accent subtlety 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 I've been telling all my friends about you", is clearly said in Hall's native British accent.
- 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 BPD officers. Jem, however, gives himself away by carrying his money bag with him, while Doug manages to escape because he behaves like every other cop at the scene.
- Pet the Dog: We figure that Doug's the 'good' criminal when, while Jimmy's screaming 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 the guy he killed had been planning on killing Doug, and Jem intercepted him en route.
- Pretty Little Headshots: Every member of Doug's gang goes down like this.
- Pseudo Crisis: Inverted. After their second robbery, the team races across the Charlestown Bridge (leading out of the North End across the river to Charlestown) before the police can 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 van and prepare to torch it... and then they turn around and see a cop staring in wide-eyed surprise at them and their weapons. After a few moments staring at each other, the cop turns his head the other way and allows them to flee.
- Psycho for Hire: Jem seriously shows signs of this.
- Reality Is Unrealistic: There were a few complaints about the scene where the lone cop drives off after staring at the four armed robbers, but Affleck based it on an actual event that happened to a bank robber he interviewed in prison.
- Actually quite smart on the part of the officer: he was facing off against four men, armed with what are obviously automatic weapons that they have no hesitation in using. Even reaching for his radio could've resulted in him getting shot full of holes. Instead, he calmly drove away, waited until they were out of sight, and then called dispatch, saving his life and preventing a potentially dangerous (for bystanders) shootout.
- Red Oni, Blue Oni: Jem (red) and Doug (blue).
- Red Right Hand: Subverted. Even though there was a scene based around Doug being scared shitless because Claire might see Jem's neck tattoo, which she witnessed during the first heist, it never comes up again, nor does it affect the heroes in any way afterward.
- Shell-Shock Silence: Used to great effect during the final heist, when the SWAT team throws flashbang grenades into the parking garage at Fenway Park.
- Spanner in the Works: Surprisingly, it's not Claire but Krista who sells the protagonists out at the end.
- Start My Own: Doug's father tried this. It didn't work out.
- Suicide by Cop: James' final fate.
- Sympathetic Criminal: To an extent.
- 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 postman uniforms.
- Villain Protagonist
- 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.