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1* AbilityOverAppearance: Krista was written to be 37, a bitter chain smoker with a raspy voice. Creator/BlakeLively was only 21 and had to lobby hard for the role, but ultimately impressed enough to cast her.
2* CareerResurrection: The widely lauded movie is credited with completely restoring Creator/BenAffleck's credibility as an actor, as well as showing his good promise as a director. It also proved that ''Film/GoneBabyGone'' wasn't a fluke.
3* {{Corpsing}}: When filming the first robbery, Creator/RebeccaHall had a hard time keeping a straight face. The reason was because Creator/BenAffleck would direct while in full costume in a skull mask.
4* DirectedByCastMember: Creator/BenAffleck as Doug.
5* EnforcedMethodActing: Self-inflicted. Creator/JeremyRenner surrounded himself with actual convicted bank robbers in Charlestown to properly get into character as part of his research.
6* ExecutiveMeddling:
7** The studio wanted the book's ending [[spoiler: where Doug dies and Krista gets the money]]. But test audiences disliked it and preferred the theatrical ending - [[SubvertedTrope so it was left in]]. The other ending was filmed and included as an extra in the Blu-Ray release.
8** [[spoiler: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.
9* FakeAmerican: Claire and Fergie are played by British actors (the latter is also a case of FakeIrish).
10* PlayingAgainstType: Creator/BlakeLively, best known as the glamorous Serena van der Woodsen on ''Series/GossipGirl'' at the time, as a trashy alcoholic.
11* ThoseTwoActors: Creator/TitusWelliver and Slaine were in the previous film that Creator/BenAffleck directed, ''Film/GoneBabyGone'', which included Ben's brother Creator/{{Casey|Affleck}}. Welliver and Creator/VictorGarber (Claire's boss) would also appear in Affleck's next film ''Film/{{Argo}}''.
12* ThrowItIn: 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.
13* WhatCouldHaveBeen:
14** Creator/MarkWahlberg was the original choice for James Coughlin, but he was too busy filming ''Film/TheFighter''. It was Creator/CaseyAffleck who recommended Creator/JeremyRenner to his brother. Creator/BenAffleck would later call Renner the EnsembleDarkhorse in the cast.
15** [[spoiler: 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.

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