Corrected entry: In the scene where the four guys are walking up to the Harvard bar for the first time, Morgan is asking Will how he was fired from his janitorial job, and then Chuckie offers Will a job working construction. Will in fact does not loose his job before this scene. This is because later, when Lambeau asks the men in the Buildings and Grounds office about Will, Will's boss says that he "didn't show up for work today," meaning that he still had his job. They would not be expecting Will had he been fired. If he was fired, the movie never attempts to explain why. (00:15:30)
Corrected entry: When Will is telling Gerald that he wants to meet at Sean's office instead, because going to MIT was to far of a commute, doesn't make much sense. Bunker Hill Community College is much more of a commute than going to MIT, especially if you're coming from South Boston on the Redline.
Corrected entry: Skylar has already been admitted to Stanford Med when the movie takes place. However, there are several references to the fact that Skylar is taking organic chemistry (O-Chem). Since O-Chem is a requirement for most undergraduate pre-med courses, it is unrealistic for her to be taking it in the last semester of her undergrad career. Additionally, despite the fact that O-chem isn't required for the MCAT, it is unlikely that a top school like Stanford would accept her without seeing her O-Chem grades.
Corrected entry: When Gerald and Sean talk about Will wasting his potential, Gerald refers to Einstein as a Swiss patent clerk who did physics in his spare time instead of getting drunk each night with his buddies in Vienna. Einstein worked in Bern/Switzerland, whereas Vienna is the capital of Austria, where Einstein never lived. (01:13:15)
Corrected entry: After they leave the bar in Harvard square they show them on their way home going over the Longfellow bridge as the sun rises. This bridge connects Cambridge to Boston and is located approximately two miles from the location of the bar. Since all bars close no later then 2:00 A.M. it must have taken them three hours to drive two miles. (00:22:10)
Corrected entry: In the scene where Will and the crew fight the guys at the basketball court, it appears Ben puts the car into park then turns around and threatens his brother to get out of the car and fight. But after he turns around and goes to get out of the car, it looks like he puts the car in park again.
Corrected entry: The part of the movie when they're on their break at the construction site when Ben Affleck's character is telling Matt Damon's character that he wishes one of these times when he goes to pick him up he won't be there...well, the chimney behind them has smoke that came out of it but none of it is moving, and for that entire scene the fog/smoke stays in the same place.
Corrected entry: This is sort of a combination of trivia and a revealing mistake. In the scene where Robin Williams is joking with Matt Damon about his wife farting in bed, if you pay close attention you'll notice that the camera shakes quite a bit. This is because the camera-man is laughing along with Williams and Damon. (00:56:35)
Corrected entry: In the scenes where Matt Damon is riding the subway alone it is apparent that he's riding the Red Line, going by the outside views of the train. But the inside views are NOT of any Red Line train, nor are they of any subway in the Boston area. No subway in Boston has those suspended handles for passengers to hold on to. And the Red Line subway has black-colored cushioned seats, all facing each other. The subway in the movie has non-cushioned plastic seats of various colors and they are facing several different positions. As someone who takes the Red Line to work every day I can definitely say that Matt Damon is not sitting in any Red Line subway at any time in the movie.