Donovan Donaly (Geoffrey Rush), a soap opera producer, comes home unexpectedly early to find his wife Bonnie (Stacey Travis) with her ex-boyfriend, a pool cleaner named Ollie (Jack Kyle), even though the Donalys have no pool. Miles Massey (George Clooney), a top divorce attorney and the inventor of the "Massey Prenup", a completely foolproof prenuptial agreement, becomes Bonnie's lawyer. He is victorious in the divorce case, leaving Donovan with nothing. Meanwhile, Rex Rexroth (Edward Herrmann) is having a sexual role-playing session with a blonde in a motel room when a private investigator named Gus Petch (Cedric The Entertainer) bursts in and records everything with a video camera. He takes the video to Rex's wife, Marylin Rexroth (Catherine Zeta-Jones), who married Rex solely to obtain wealth and independence via a divorce. Rex hires Miles. Marylin learns from her friend, a wealthy fellow serial divorcee named Sarah Sorkin (Julia Duffy), that Miles is a dangerous opponent.After Marylin and her lawyer, Freddy Bender (Richard Jenkins), fail to reach a settlement with Miles and Rex, Miles asks Marylin to dinner, where they spar. Miles hires Gus to steal some information for him. In court, Miles has a concierge named Heinz, the Baron Krauss Von Espy (Jonathan Hadary) testify that Marylin asked him several years ago to find her a rich, easily-manipulated husband. As a result, Marylin winds up with nothing. Miles's aged boss, Herb Myerson (Tom Aldredge), congratulates Miles on his fine work. Marylin wants revenge and gets it with the help of broke soap producer Donaly, whom she finds living on the street clutching his Emmy statuette. Soon after, Marylin shows up at Miles's office with her new fiance, an oil millionaire named Howard D. Doyle (Billy Bob Thornton). Though Marylin insists Doyle sign the Massey Prenup, he destroys it during the wedding as a demonstration of his love. A few months later, Marylin divorces Howard and receives the "Doyle Oil fortune".Marylin later bumps into Miles in Las Vegas, where he is the keynote speaker at a convention of divorce attorneys. They discover that they both are lonely people despite their wealth. Miles marries her on the spur of the moment. He insists on signing the Massey Prenup to show that he is not doing it for her money, but she tears it up. He announces at the convention that he is abandoning divorce suits in favor of pro-Bono work in East Los Angeles. However, Miles soon discovers that Howard D. Doyle is in fact just an actor from one of Donaly's soap operas. Marylin has tricked him and now his wealth is exposed to asset stripping.Miles' boss is most displeased with this turn of events and demands that something be done to save the firm's fearsome reputation. He refers Miles to a hit-man named Wheezy Joe (Irwin Keyes). But when Miles learns that Marylin's ex-husband Rex has died of a heart attack, leaving her millions because he never changed his will, Miles rushes to save his wife. Marylin however is in no danger. Her rottweiler guard dogs have Wheezy Joe surrounded and she offers to pay him double to switch sides. When Miles and his assistant Wrigley arrive, they are confronted by the hit man. In the confusion of the ensuing struggle, Wheezy Joe mistakes his Salbutamol inhaler for his gun and shoots himself in the head. Later, Miles and Marylin meet to negotiate their divorce. Miles pleads for a second chance and retroactively signs a Massey Prenup. She tears it up, and they kiss.Marylin tells Miles that she has suggested an idea to Donaly for a TV show, and Gus Petch becomes the host of America's Funniest Divorce Videos.