Chuck Hogan’s novel Prince of Thieves opens with a toast:

Raise a Glass. Solemn now:

To The Town.

To Charlestown, our one square mile of brick and cobblestone. Neighborhood of Boston, yet lopped off every map of the city like a bastard cropped out of a happy family portrait.

Ben Affleck grew up in Cambridge, only a few miles away from Charlestown, but to him the distance between the two places felt vast. Unfair or not, Charlestown had a reputation. “It was like a different world,” the actor and filmmaker says. “When I was a kid, I was scared to go there. Violence, unsolved murders ...”

And armed robbery.

In 1995, The Boston Globe reported that the neighborhood was “a community to which more armored car robbers are traced than any other in the country, according to FBI statistics.” Hogan recalls reading that and filing it away. It later served as inspiration for the Massachusetts native’s third book. Published in 2004 and set in the ’90s, it follows a team of stick-up men led by Doug MacRay, a washed-up NHL draft pick and recovering addict whose traumatic childhood has led him to follow his incarcerated father into the family business.

The story appealed to Affleck. A decade after establishing his Boston bona fides by cowriting and appearing in Good Will Hunting with Matt Damon, he was offered a chance to adapt Prince of Thieves for the screen. “It was concealing a character-based drama centered around themes that I was interested in, particularly the theme of children paying for the sins of their parents,” Affleck says. “But wrapping that in the sort of candy shell of a heist movie.” Beyond the flashy heists, The Town—renamed because Prince of Thieves had already been used as the subtitle of Kevin Costner’s version of Robin Hood—is a movie about fate, loyalty, and morality, and how those things commingle. MacRay is pulled between the devil and angel who sit on his shoulders: Jem, who spent nine years in prison for killing someone who was supposedly planning to kill Doug; and Claire, the bank manager Doug falls for after a job.

[Read Alan Siegel's oral history of The Town, with commentary from its cast and crew.]