- Ability over Appearance: Krista was written to be thirty seven, a bitter chain smoker with a raspy voice. Blake Lively was only twenty-one and had to lobby hard for the role, but ultimately impressed enough to cast her.
- California Doubling: Averted. Thanks to the 25% tax credit created for filmmaking in the Commonwealth of Massachusetts after the success of The Departed (which had been forced to shoot partially in New York), almost everything you see was filmed on location in Boston. Played straight for an establishing shot, where a shot of City of Angels Medical Center in Los Angeles is used for some reason to represent Beth Israel Deaconess Medical Center.
- Career Resurrection: The widely lauded movie is credited with completely restoring Ben Affleck's credibility as an actor, as well as showing his good promise as a director. It also proved that Gone Baby Gone wasn't a fluke.
- Directed by Cast Member: Ben Affleck as Doug.
- Enforced Method Acting: Self-inflicted. Jeremy Renner surrounded himself with actual convicted bank robbers in Charlestown to properly get into character as part of his research.
- Executive Meddling:
- The studio wanted the book's ending where Doug dies and Krista gets the money. But test audiences disliked it and preferred the theatrical ending - so it was left in. The other ending was filmed and included as an extra in the Blu-Ray release.
- Dez's death was going to be more violent, but because the scene was being filmed at Fenway Park, Major League Baseball would have to sign off on it. They didn't so it was toned down.
- Fake American: Claire and Fergie are played by British actors (the latter is also a case of Fake Irish).
- Fake Irish: Averted in some notable cases (e.g. Ben Affleck has Irish ancestry, which is expanded into Doug's character, and Slaine is outspokenly Irish-American and it is seen in his performance as Gloansy), but mostly played straight.
- Playing Against Type: Blake Lively, best known as the glamorous Serena van der Woodsen on Gossip Girl at the time, as a trashy alcoholic.
- Those Two Actors: Titus Welliver and Slaine were in the previous film that Ben Affleck directed, Gone Baby Gone, which included Ben's brother Casey. Welliver and Victor Garber (Claire's boss) would also appear in Affleck's next film Argo.
- Throw It In!: The sequence of a cop turning away as he sees the robbers escaping wasn't in the original script. Ben Affleck added it in after interviewing a bank robber in prison - who said it happened to him.
- What Could Have Been:
- Mark Wahlberg was the original choice for James Coughlin, but he was too busy filming The Fighter. It was Casey Affleck who recommended Jeremy Renner to his brother. Ben Affleck would later call Renner the Ensemble Dark Horse in the cast.
- Dez's death scene had to be edited down because it was deemed too violent. The initial cut had blood splattering all over the ambulance.
Trivia / The Town