Out of Sight (1998)

When ex-con Jack Foley (George Clooney) robs a bank, his car goes dead, and Foley lands in a Florida prison. His escape from prison doesn't go as planned, since it's witnessed by deputy federal marshal Karen Sisco (Jennifer Lopez). Foley's pal Buddy Bragg (Ving Rhames) intervenes, with the result that Sisco winds up in the trunk of the getaway car with Foley, and the two realize they're attracted to each other, despite being on opposite sides of the law. However, that doesn't stop Sisco from her mission to capture Foley, who has spent much of his life in prison. Flashbacks introduce Foley's fellow prisoners, including dim dude Glenn Michaels (Steve Zahn), violent Maurice "Snoopy" Miller (Don Cheadle), and insider trader and billionaire Richard Ripley (Albert Brooks), who talks too much about his wealth. This later leads to a break-in at Ripley's posh Detroit estate by Miller, his brother-in-law Kenneth (Isaiah Washington), and menacing White Boy Rob (Keith Loneker). While seeking a hidden safe, the group threatens Ripley's housekeeper Midge (Nancy Allen). Foley and Bragg are in on this operation, but they wind up outwitting the others, and Sisco is close on their trail.