Ben Affleck’s crime spree: the brutal robberies that inspired The Town

“One blue-collar Boston neighbourhood has produced more bank robbers and armoured-car thieves than anywhere in the world: Charlestown.” 

These words flash up on screen at the opening of Ben Affleck’s 2010 crime thriller, which follows a crew of Boston robbers as they rise from local bank jobs to a hit on Fenway Park. The sentence subtly shapes the viewer’s response to the daytime bank heist that starts the film. As robbers in Hallowe’en masks brandish machine guns and snarl at the terrified staff in heavy Boston drawls – “Everybody on the f----n’ flaar!” – you wonder: is this just an average day in Charlestown?

By the time Affleck directed and starred in the film, Boston’s oldest neighbourhood, a small squarish outcrop situated north of the Charles river, was no longer the crime capital of America. Police figures from 2010 showed that Charlestown accounted for barely 2 per cent of all Boston robberies (not just bank robberies).

According to FBI statistics from the same year, the entire state of Massachusetts had fewer than 3 per cent of all bank robberies nationwide. If the criminal culture that The Town associated with Charlestown’s Irish-Catholic working-class community ever existed, it had dwindled away with the neighbourhood’s traditional residents.

“All they see are yuppies. They think there’s no more serious white people in Charlestown,” says local girl Kris (Blake Lively) early in the film. Her words had already come true. In 2010, estate agents were pitching waterfront redevelopments to young professionals and families. “It’s gentrified and diverse now,” a local TV show host told The Christian Science Monitor. “It’s not the same town as it was in the early 1990s and the 1980s.”

Tensions between the locals and wealthier transplants underscore the film. At heart, it’s a story of social mobility. Douggie, played by Affleck, is a man trying not to die on the street he was born. The gentrification of Charlestown is the huge pile of rotting wood fueling The Town’s bonfire of crime. It’s ironic that by the time the film came out, the process was largely complete.

But what about in the 1980s and early 1990s? FBI figures reveal significantly higher crime rates pre-gentrification. In 2018, there were just over 4,000 robberies in Massachusetts – compare that to 1980, when there more than 13,500. The annual average hovered above 10,000 for the next 15 years. It’s worth bearing in mind that these are state-wide statistics, which do not differentiate between neighborhoods.

But if Charlestown’s present reality as a yuppie stronghold is easy to establish, its past status as a mythical crime mecca is difficult to entirely dismiss. Most of the heists in The Town were inspired by real crimes from that era. In adapting the script, itself adapted from Chuck Hogan’s novel Prince of Thieves, Affleck and Aaron Stockard (with whom he also worked on Good Will Hunting and Gone Baby Gone) changed the cinema setting of the second heist to an armoured-car robbery and car chase based on a real incident that took place in Harvard Square. 

In March 1995, two men held the guard of an armoured car at gunpoint as he tried to deliver cash to a branch of the Bank of Boston on Massachusetts Avenue. They wore wigs, fake bears and masks; in the film, brilliantly, these became nun masks and habits. As they fled with a bag of cash containing roughly $281,000 (£180,000 then), another guard opened fire. In the film, the crew get away, largely thanks to the kind of driving that puts Daniel Craig to shame. “That’s how you drive a f----n’ caaar,” declares the getaway driver, Gloansy (played by rapper Slaine).

In real life, they were not so lucky. Both robbers were shot, one in the back and one in the head, and the getaway driver promptly rear-ended a parked car. All three men were arrested and sent to prison. All three were 25 or under. All three were from Charlestown. A man who was in the square at the time recalls thinking: “Who’s crazy enough to pull off a bank robbery at noon in Harvard Square?” Charlestown guys.

Another botched job referred to in the film – the one for which Douggie’s father (Chris Cooper) was sent down for life for killing two guards – was also inspired by a notorious bank heist gone wrong. Shortly after 9am on August 25 1994, an armoured car pulled up outside a NFS Savings Bank in Hudson, New York.

The robbers were waiting. After shooting one guard outside the car and one inside the bank, they escaped in a rental truck. A woman who saw it speeding past reported it to the police, who matched the report to a truck rented the day before in nearby Medford by a man already suspected of a string of robberies. Tyre marks matched those found in Houston, and five men were eventually convicted. They were all from Charlestown.

The Town’s numbers may not add up, but the atmosphere it creates seems genuinely authentic to the old Charlestown and to its proudly Irish, proudly blue-collar inhabitants. When he took over the project – Fatal Attraction’s Adrian Lyne was originally down to direct – local boy Affleck decided he wanted to make this as much of a “Boston film” as he possibly could.

He grew up in Cambridge, which was close enough to Charlestown for him to know a little about it. (His co-star John Hamm once said that walking around Boston with Affleck was like walking around with the mayor.) Or rather, close enough for him to understand how little he knew about it. Determined to get a better grip on the place, he brought in another local, his old school friend Stockard, and began an intensive period of research.

Location scouting was uppermost in his mind. The Ringer’s Bill Simmons, who lived in Charlestown for eight years, said on The Rewatchables that, of all films, “this one makes me the most nostalgic for Boston.” The bars in the film are real Charlestown bars: Old Sully’s (for townies), where Douggie and Jem meet early on, and New Sully’s (for yuppies), where Hamm’s FBI officer approaches Niki.

The first bank robbery in Melrose was shot on location. Even the prison is real: the scene in which Douggie visits his father was shot on location at the maximum security MCI-Cedar Junction, the first time anything had been filmed there.

The production’s biggest scoop, location-wise, was being granted permission to shoot the Fenway Park heist scene in the real Fenway Park, home of the Boston Red Sox. Shooting there had been a condition of Affleck taking on the film. He was given just 13 days, during which the sound of automatic gun fire spooked a wedding party that had hired Fenway as a venue and were apparently not made aware that there was also a film shoot in progress. The guests ran for cover.

Affleck also embarked on a series of interviews with locals, including convicted robbers and members of the FBI violent crimes force. These were to prove fundamental to the film’s success, yielding some of its most memorable moments.

For instance, the shot in which a cop supervising a traffic stop takes one long look at a carload of nun-masked robbers and turns the other way? This really happened – it was described to Affleck by a man serving time. Rebecca Hall’s character asking Douggie why the kids with whom she volunteers call her a “tunie”? Extremely plausible. Affleck said he picked up the term from a guy at New Sully’s bar: “I asked, ‘What’s the thing with the Tunies?’ And he said the Tunies moved in and the Townies stole all their car stereos. They had all these Blaupunkts. They stole their tunes.”

The interviews also gave The Town an on-tap supply of authentic extras. They ran mass auditions of up to 1,000 people at a time, Affleck recalls. Some were ex-convicts for whom a judge’s permission had to be sought for them to carry weapons, even fake or unloaded ones. “Pretty much everyone on the set was an ex-con of some sort,” Jeremy Renner told the LA Times. “And there were probably a couple of guys there who were still robbing banks.”

And on Affleck’s instructions, Blake Lively, a California girl, spent three months hanging around with locals in bars and apartments to prepare for her role. Her performance was savaged by some critics – it “features the Bride Wars of Boston accents,” Wesley Morris wrote in the New York Times – but history has been kinder to her. Bill Simmons says “there were a lot of Boston ladies like Kris in real life.” It seems likely that Lively had met a few. 

The Town took $23.8 million (£18.4 million) at the box office on its opening weekend, from a budget of just $37 million (£28 million). It went on to make $154 million (£119 million) worldwide. But not everyone was happy with the image of Charlestown given to a generation of moviegoers. Some residents felt it portrayed the locals as – in the words of one quoted in The Christian Science Monitor, “a bunch of dumb bums”.

But does it? The Town may have taken a small place with a complicated history and declared it a cesspool of violent criminals – but they aren’t dumb ones. Nor bums. When fans of The Town think of Charlestown, they think of banks and bars and punchlines. We all want to chortle, like Jem, “there goes college soccaaar”,  while shooting a guy we don’t like in the knee. We all want to drive a “f----n’ caaar” like Gloansy. We all want to be from Douggie’s Charlestown and we all know it’s a fantasy.