A career bank robber, Jack Foley, and a U.S. Marshal, Karen Sisco, are forced to share a car trunk during Foley's escape from a Florida prison. After he completes his getaway, Foley is chased by Sisco while he and his friends—right-hand man Buddy and unreliable associate Glenn—work their way north to Bloomfield Hills, a wealthy northern suburb of Detroit. There they plan to pay a visit to shady businessman Ripley, who foolishly bragged to them in prison years before about a cache of uncut diamonds hidden in his home.
As Foley and Buddy discuss their plan, Foley returns to his apartment room. Shortly after, Sisco enters Foley’s room with her gun drawn. She approaches the bathroom, the door is slightly open and she looks in to see Foley taking a bath with his eyes closed. Foley suddenly grabs her gun and smiles at her, she does the same. He the guides her into the tub with him and they make out passionately. Sisco is abruptly woken up, it had been a dream. Much to her disappointment.
Glenn spills the diamond plot to a vicious criminal named Maurice Miller, who also spent time in jail with Jack and Ripley. Maurice then plans to rob Ripley's mansion with his own crew, including Kenneth and White Boy Bob. Maurice and Foley agree to team up on the job and split the earnings, while Glenn gets cold feet and ducks out after Maurice forces him to help kill a drug dealer, with Sisco allowing him to escape.
Before the robbery, a romantic interlude between Foley and Sisco takes place in a Detroit hotel, but the question of whether she is really pursuing Foley to arrest him or for love ends in a showdown during the robbery at Ripley's home and adds to "the fun" Foley claims they are having.
In the course of the heist, White Boy Bob accidentally shoots and kills himself after tripping on the stairs, while Foley shoots and kills Kenneth as he attempts to sexually assault Ripley's housekeeper/lover, Midge. Sisco, having followed the team to Ripley's home, shoots and kills Maurice, and arrests Foley after he implores her to kill him, telling her to "pretend [he’s] someone else". Buddy is able to slip away with Ripley's diamonds.
The next morning, Foley is loaded aboard a van to be returned to prison in Florida. Another detainee, Hejira Henry, boards the van and mentions to Foley that he has escaped from prison nine previous times, and was deliberately placed by Sisco in the same van as Foley. Sisco smiles as the van leaves for Florida.
George Clooney as Jack Foley
Jennifer Lopez as Karen Sisco
Ving Rhames as Buddy Bragg
Don Cheadle as Maurice Miller
Steve Zahn as Glenn Michaels
Albert Brooks as Richard Ripley
Dennis Farina as Marshall Sisco
Luis Guzmán as Chino
Isaiah Washington as Kenneth
Nancy Allen as Midge
Keith Loneker as White Boy Bob
Catherine Keener as Adele
Viola Davis as Moselle Miller
Paul Calderón as Raymond Cruz
Wendell B. Harris Jr. as Daniel Burdon
Michael Keaton as Ray Nicolette (uncredited)
Samuel L. Jackson as Hejira Henry (uncredited)
adapted from Elmore Leonard's 1996 novel of the same name