The Town: Ben Affleck's Heist Movie Love Letter to Boston – Den of Geek

January 15, 2022
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Ben Affleck made a minor heist movie classic with The Town, a thriller which shines light on the legendary history of Boston's Charlestown.
It’s not wedding bells which break up the old gang in Ben Affleck’s The Town, it’s witness protection. The romance in the middle of the film is only there to delineate the boundaries between heist film and crime procedural. The movie’s center is Charlestown, right across the bridge from the rest of Boston, a legend in illicit locales. The blue-collar neighborhood “produced more bank robbers and armored car thieves than anywhere else in the world,” according to the movie’s prologue. Affleck’s second film as a director charts the fall of a mythic heist gang and the streets which made them.
The Boston area was prime cinematic crime fields during the early 2000s. In Black Mass, Johnny Depp plays South Boston mobster James “Whitey” Bulger, an Irish gangster who informed on the Italian mob to the FBI. Some of the scenes were shot on the real crime locations depicted. Martin Scorsese’s The Departed cast Jack Nicholson as Frank Costello, who was loosely based on Bulger. The city also set the scene for Clint Eastwood’s Mystic River, and Affleck’s directorial debut, Gone Baby Gone, both based on books by local crime novelist Dennis Lehane.
But one of the greatest films about Boston goes back to 1973. The Friends of Eddie Coyle starred Robert Mitchum in the title role and Peter Boyle as a hitman who ran a bar. It is sloppy, sleazy, quickie. And it’s absolutely authentic. The car chases get stuck in traffic, and the dialogue comes directly from testimony.
The Town is loosely based on Chuck Hogan’s novel Prince of Thieves. The 1995 article in The Boston Globe, which inspired the film’s prologue, actually noted “more armored car robbers are traced” to Charlestown than any other neighborhood in the country. This is based on FBI statistics at the time. This isn’t because those criminals made the sloppiest getaways. It is because the small community adheres to omerta, silence unto death. If they get popped, they do the time. They don’t squeal. They don’t rat. They don’t fink.
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The crew at the center of The Town resembles a gang of five masked robbers who pulled holdups from 1990 to 1995. After a seven-day trial, they were convicted on 54 of 55 counts of robbery, including one which resulted in the death of two armored car guards. They went to jail because there were cracks on the pavement, leaks on the street.
“Numerous career bank robbers threw in the towel and testified in this trial,” Assistant U.S. Attorney Michael Connolly said at a news conference at the time. “So many broke the code, shattered the code. Many of them testified that they had grown tired of a life of stealing, of drugs, of broken relationships.”
Affleck gives the gang its last hurrah on-screen. Something the character of James (Jeremy Renner), aka Jem, could appreciate. Jem would rather battle it out with the law than go back to prison. Affleck’s Doug MacRay, the leader of the gang, is the one who’s gotten tired of the life. He’d be happy to settle down with his former hostage, Claire Keesey (Rebecca Hall). He loves her enough not to kill her, but not enough to testify.
Heist movies are filled with criminals who want to pull one last big job and settle down. Al Pacino’s Sonny in Dog Day Afternoon wants enough money to give a better life to his wives. In Stanley Kubrick’s The Killing (1956), a marriage-minded Sterling Hayden leads a crew to take down one last racetrack for $2 million. Affleck’s big killing in The Town is Fenway Park, and over 60 years later, the take is the same. But it still has to be divvied up among the team. 
In the history of crime, the best crew was headed by John Dillinger. He robbed banks but let the civilians in the banks keep their money. Dillinger assembled a crack team and he himself would hop over the bank booths like a jack-rabbit, hence his nickname. He’s been played by Johnny Depp, Warren Oates, and Lawrence Tierney.
Ocean’s Eleven set the cinematic standard for a heist team. It included a mastermind, a distraction, a partner, a coordinator, a backer, hacker, con man, and gadget guy. It also had a scheme so ingenious that Frank Sinatra supposedly considered pulling the job over doing the film. In Quentin Tarantino’s Reservoir Dogs (1991), the crew had color-coded names; in Butch Cassidy and the Sundance Kid they wore 10-gallon hats. Every large theft needs an inside man, but Inside Man (2006), directed by Spike Lee, had Clive Owen as a bona fide genius.
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By contrast, Affleck’s Doug MacRay heads a four-man gang. While they don’t have a street name, FBI Special Agent Adam Frawley (Jon Hamm) calls them “The-Not-Fucking-Around-Crew.” They plan their jobs meticulously, bleaching crime scenes to eradicate DNA traces, and nuking the security tapes in the bank’s own microwave. The gang torches their escape cars and their transfer vehicles. They’re locked, loaded, and trained in automatic weapons, and launder their take immediately. They get their tips and kick up to local crime lord Fergus ‘Fergie’ Colm, played by veteran character actor Pete Postlethwaite. He poses as a florist, just like Dean O’Banion, the Irish gang leader who celebrated St. Valentine’s Day with Al Capone in Prohibition Chicago.
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Affleck’s Doug almost got out of his predetermined life. He was a local hockey star who got drafted by the NHL, but started beating on his own teammates and got sent back home. He goes into the family business. His father, Stephen MacRay (Chris Cooper) was a thief, just like his father, and all of Doug’s friends were thick with thievery.
Jem is his right hand muscle, and unquestioning backup. When Doug wakes Jem up in the middle of the night to do some damage and ask no questions, the only thing his friend wants to know is which car they should take. Jem spent nine years in prison for killing a local thug who was planning to kill Doug.
Jem is also Riff to Doug’s Tony in West Side Story. They have an allegiance which goes “from womb to tomb,” and “sperm to worm.” Jem’s family took Doug in after his mom deserted him, and his father fell apart for a little while. Jem is furious when he finds Doug cozying up to Claire, the bank manager who could finger them to the Feds. His first reaction is to “take her out of the equation.”
The film makes Jem out to be the loose cannon in the arsenal, but he makes criminal sense. MacRay, who is a recovering addict with mommy issues, is more of a sociopath than Jem, who is only living the way the streets taught him. MacRay is a narcissist who uses Jem’s sister Krista (Blake Lively) for bathroom quickies, and Claire as a loophole.
Claire represents the real problem at the center of the proceedings. Besides being the lovable and erudite wrinkle in the scheme, she is not a “townie,” someone who was raised in the neighborhood. She is the interloping gentry and renovates Doug’s headspace. Claire foretells the doom of Charlestown’s criminal culture. The Town was originally set to be a three-and-a-half-hour-long epic directed by Fatal Attraction’s Adrian Lyne.  Affleck turns it into a redemption story which beats the bank alarm at under two hours.
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Affleck was born in Berkeley, California but grew up in Cambridge, also across the Charles River from Boston but far removed from the inner-city neighborhood of the film. He heard stories about Charlestown’s reputation for bank robberies and its strict code of silence. For the film, Affleck talked to locals, visited the maximum-security prison MCI—Cedar Junction, and consulted with the FBI Violent Crimes Task Force in Boston. He also ran afoul of the law himself, recruiting real ex-cons as extras and giving them guns. Ex-felons are not allowed to hold even fake weapons. Affleck had a personal stake in the film that went beyond proving himself as a sophomore director.
The Town captures the locale expertly, and the atmosphere masterfully. Even with the shorter length he’s afforded, Affleck tells multiple stories. It has a failed romance, a foiled heist, an unsolved crime, enough car chases for three movies, and yet is a coming-of-age film and a portrait of an era’s end. It is also quirkily structured, vaguely biographical and personal. This makes it a mini-epic. It’s not The Godfather of caper films, but it is a heist movie must-see.
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Written by
Tony Sokol |
Culture Editor Tony Sokol is a writer, playwright and musician. He contributed to Altvariety, Chiseler, Smashpipe, and other magazines. He is the TV Editor at Entertainment…
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