The Lookout
(2007)

After the heist goes bad, Gary and Bones take Lewis (Jeff Daniels) hostage in order to get Chris (Joseph Gordon-Levitt) to return the money.  Chris demands they meet him at the mayor's Christmas tree to make a trade.  Gary has been shot in the stomach, so Bones tries to beat the location of the money out of Chris when they meet.  Gary knows Chris writes everything down, so with gun to Chris' head, demands his notebook.  The book leads them to the location, where Chris digs.  Chris remembers he left a gun in one of the bags of money.  Bones forces Lewis to kneel on the ground, while demanding Chris get the second bag of money.  While Bones leans back to pull the trigger, Chris shoots him with the hidden gun.  Gary has fallen on the ground, nearly dead from his stomach wound.  He asks Chris, "Don't you remember?" and Chris kicks his inhaler away from him, and Gary dies. 

In voiceover we learn that Chris returns the money and confesses his role in the heist.  Since the FBI doesn't believe someone in his mental state could pull off the crime and the security tape doesn't show him taking a major role, he is basically let off the hook.  He later gets a bank loan to open the restaurant, and he is trying to work up the courage to talk to Kelly, the girl who survived the crash at the beginning of the film.

Thanks Jana!