Director: Ben Affleck
Stars: Ben Affleck, Rebecca Hall, Jeremy Renner
Plot: As he plans his next job, a longtime thief tries to balance his feelings for a bank manager connected to one of his earlier heists, as well as the FBI agent looking to bring him and his crew down.
Jeremy Renner surrounded himself with actual convicted bank robbers in Charlestown, for research and to help him nail the accent.
While filming of the first robbery, Ben Affleck would sometimes direct while in full costume, including the skull mask. Rebecca Hall was unable to keep a straight face, and found it difficult to take direction from him when he was in costume.
Chris Cooper's scene was shot on location at MCI-Cedar Junction, a maximum security prison in Massachusetts. It was the first time anything was filmed there.
In one scene, there is a shot of the TV playing a movie where a white truck rides into a Drive In Movie Lot, this is a scene from the movie "Heat", a movie that is also about bank robbers being chased by an obsessed detective.
Ben Affleck originally wanted Mark Wahlberg for the role of James Coughlin, but he was busy shooting The Fighter (2010), so the role went to Jeremy Renner, who ended up receiving the Oscar nomination for Best Supporting Actor.
A large section of the movie takes place at Fenway Park. Affleck is a devoted Red Sox fan and attends games regularly.
The scene where the cop turns away when he sees the masked armed robbers getting away is based on an actual event. Ben Affleck added it to the film after interviewing a bank robber in prison.
The studio heads initially wanted the novel's ending, in which Doug is mortally wounded during his shootout with Fergie and dies in Claire's arms in her apartment. The ending was filmed, but test audiences approved the theatrical version, in which Doug survives.
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.
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 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. While Affleck was happy with the theatrical cut, he said that an Extended Cut on the DVD and BluRay will feature deleted scenes on top of the cut footage. He also said that while the theatrical cut of The Town is a close adaptation of the novel 'Prince of Thieves', the extended cut is more true to the book.
Ben Affleck was struggling to find the right actor for the role of James Couglin. His younger brother Casey Affleck suggested Jeremy Renner, who he'd worked with in The Assassination of Jesse James by the Coward Robert Ford (2007).