Jack Foley (George Clooney) is a professional bank robber who has robbed more banks than anyone on the FBI's computer. Most of them with his partner Buddy Bragg (Ving Rhames). Karen Cisco (Jennifer Lopez) is a Federal Marshall who manages to catch Foley as he escapes from prison. But Foley and Buddy overpower her and take her hostage while they escape. Jack makes a connection with Cisco as they lie in the trunk of Karen's car together and pretty soon, Jack finds himself wanting to keep her around, so that he can see what it would've been like if they met under different circumstances. The sub-plot to this film shows a loudmouth convict named Glenn Michaels (Steve Zahn) who learns of a stash of uncut diamonds in the house of another convict named Richard Ripley (Albert Brooks) who pays for protection in prison from the volatile gangster Maurice Miller (Don Cheadle). Michaels sets up the score for Foley, Bragg and himself, but find Miller and his crew forcefully joining the squad.
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