Continuity mistake: When they are crossing the bridge to go back into Boston, after leaving the bar in Cambridge, a Red Line subway train is shown and then in the next shot there are several buildings in the background as they cross the bridge. These buildings are in Boston, but this shot has them driving away from the buildings, which means they would be re-entering Cambridge.
Continuity mistake: In the scene "When Did You Know?", when Will tells Sean that he read his book last night, an aerial shot looking down at them shows Will with his foot up on the table. But two shots later Will has his foot up on the chair instead. The chair in the first shot would also be too far away for Will to reach from his own chair, so that would have been moved in the later shot for him to reach.
Continuity mistake: In the scene where they are all gathered in the bar together Ben is telling the story about his uncle. Throughout the entire scene, Ben has nothing in his hands but as he comes to the end of the story there is a camera shot over his right shoulder showing him holding a cigarette. However, when the next shot moves to in front of him, the cigarette has gone again.
Continuity mistake: At the end of the film during Will and Sean's last meeting, there is a shot showing both Will and Sean and we see Will with his hands in his lap. It then cuts to a shot over Sean's shoulder and we see Will, but now his hands are raised and his elbows are on the arms of the chair.
Continuity mistake: Near the end of the film after Chuckie realizes that Will is gone, he turns and heads back to the car. As he first goes down the steps and down the walkway you can see Morgan already sitting in the front passenger seat. As Chuckie approaches the car, however, you then see Morgan excitedly jump out of the back seat and run around the car to jump in the front seat.