Before the movie was released, Ben Affleck praised Jeremy Renner's performance. He jokingly stated that if there was a bad shot or performance from someone else in a scene, editing could easily cut to Renner looking at a napkin to make the scene work. Jeremy Renner would go on to receive an Academy Award nomination for his performance.
Jeremy Renner surrounded himself with actual convicted bank robbers in Charlestown for research and to help him nail the accent.
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 Actor in a Supporting Role.
The original cut was four hours long. After realizing that the film would never appeal to wide audiences, Ben Affleck cut the film down to two hours and fifty minutes in three days. The studio and producers loved it, but they wanted the film to be no longer than two hours and ten minutes. Eventually, Affleck cut the film down to two hours and eight minutes. While Affleck was happy with the theatrical cut, he said that an Extended Cut on the DVD and Blu-ray 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 L'assassinio di Jesse James per mano del codardo Robert Ford (2007).
Ben Affleck: [Red Sox] A large section of the movie takes place at Fenway Park. Affleck is a devoted Red Sox fan and attends games regularly.