Magnificent Bastard: Doug MacRay is a smooth, noble bank robber who works with his gang, having pulled off successful heists for years. When his trigger happy partners take bank manager Claire as a hostage, Doug ensures Claire's escape before starting a romance with her in his public persona, genuinely falling for the woman as he continues to rob armored cars and adapt to new variables on the fly to avoid capture. Forced into One Last Job by his employer Fergie under threat of Claire being hurt, Doug does his best to pull off the doomed heist, and though the whole operation is bungled by outside interferences, Doug evades detection, kills Fergie for past transgressions, and flees to the other side of the country. With the FBI agents on his tail totally fooled by his escape, Doug takes time to say goodbye to Claire and leave her a small fortune, promising to see her again one day.
Memetic Mutation: "Friendship Goals!"note Many viewers' response to the scene where Doug asks for Jem's help hurting some people but can't ask any questions and Jem only asks whose car they're going to use.
Moral Event Horizon: You know Fergie is a goner when he tells Doug that he hooked his mother on coke and indirectly caused her suicide.
Narm: The look of humiliated horror on Fergie's face when he realizes that he's about to get his crotch shot off by Doug at the end.
One-Scene Wonder: 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.
Special Effects Failure: At least twice during the North End police chase, you can see ramps in the gutters near street corners that are meant to allow the stunt drivers to clip the curbs without damaging their vehicles.
Unintentionally Sympathetic: It's hard not to feel a little bit sorry for Krista, considering she seemed to at least feel something for Doug whereas he was just using her for sex. Blake Lively described her as someone who wanted to escape her situation just like Doug, and hoped he would be her way out. The last we see of her, she's in the hospital and her daughter has been taken off her.