* AwardSnub: The film did not get a Best Picture nomination.
* CounterpartComparison:
** In an interesting way, Doug can be seen as a much darker take on Neil [=McCauley=] from ''Film/{{Heat}}''. Both men are the main characters and career criminals who rob banks. But after they plan to retire from their criminal life, both also plans to flee the cities they're living in with the woman they encounter in their lives.
** Claire and Eady. Both women are lovers to the criminal protagonists. But after finding out that the men they fell in love with happens to be living a criminal life, both [[spoiler:were forced to leave them when they're on the verge of being caught by the police.]]
* DarknessInducedAudienceApathy: Given the gritty nature of the film, it can be hard to root for any of the characters in the cast, up to and including Doug himself.
* EnsembleDarkhorse: Creator/JeremyRenner as Jem got the most praise for acting and the film's only Academy Award nomination, as well as the character himself.
* HeReallyCanAct: Creator/BenAffleck restored faith in his acting abilities and Creator/BlakeLively proved there is more to her than Serena van der Woodsen. Everyone knew Jon Hamm could already act but this showed he could go all the way.
* MoralEventHorizon: [[spoiler: You know [[BigBad Fergie]] is a goner when he tells Doug that he hooked his mother on coke and indirectly caused her suicide.]]
* OneSceneWonder: Chris Cooper as Doug's father, Stephen [=MacRay=]. Also, Pete Postlethwaite is on screen for hardly more than 5 minutes, but makes the most of every moment in an intense, genuinely frightening performance as Fergie the Florist.
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