Plot

Miles, a high-profile divorce lawyer, wins a case for his rich but adulterous client Rex Rexroth. But Rex's ex-wife, Marylin, who is no saint and is a gold-digger, plots to take revenge on Miles.

Miles Massey, a prominent Los Angeles divorce attorney has everything--and in some cases, two of everything. Despite his impressive client list, a formidable win record, the respect of his peers and an ironclad contract (the Massey pre-nup) named after him, he's reached a crossroads in his life. Sated on success, boredom has set in and he's looking for new challenges. All that changes when Miles meets his match in the devastating Marylin Rexroth. Marylin is the soon-to-be ex-wife of his client Rex Rexroth, a wealthy real estate developer and habitual philanderer. With the help of hard charging private investigator Gus Petch, she has Rex nailed and is looking forward to the financial independence a successful divorce will bring. But thanks to Miles' considerable skills, she ends up with nothing. Not to be outdone, Marylin schemes to get even and as part of her plan, quickly marries oil tycoon Howard Doyle. Miles and his unflappable associate, Wrigley, unwittingly dig themselves in deeper and deeper as they go head-to-head with Marylin. Underhanded tactics, deceptions and an undeniable attraction escalate as Marylin and Miles square off in this classic battle of the sexes.—Sujit R. Varma

Divorce attorney Miles Massey has everything, a jet, a jet washer, three gardeners (or "those little lawn people" as he puts it), and even a marriage contract (The Massey Prenup) named after him. He seems to be unstoppable and completely invincible. That is, until he meets the beautiful, dangerous Marylin Rexroth. After being completely destroyed in court, Marylin formulates a plan that puts Miles in a position where he doesn't know what to do. For the first time in his life, he doesn't have what he wants the most.—tigerchick5655

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. Donovan pulls a gun on Ollie, but Bonnie hits Donovan on the head with his Daytime TV Lifetime Achievement Award and curses him for ruining her life. Ollie escapes in his van, while Bonnie drives away Donovan's Jaguar, even as Donovan shoots at them from the balcony.

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. Miles argues in court that Donovan habitually beat his wife and threatened her with her own gun (when in fact it belonged to Donovan). Miles also argues that it was Donovan who was sleeping with Ollie. Donovan has a TV show called the sands of time, which is also transferred to Bonnie as part of the settlement.

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. Unable to afford a divorce settlement (Rex says that all his assets are mortgaged to pay for development of a series of mini malls that he is constructing), Rex hires Miles to represent him. Rex tells Miles that initially Marilyn was all hot and heavy, but with time their sex life cooled off. Rex says that he and Marilyn had an implicit understanding that they could see other people. Marylin learns from her friend, a wealthy fellow serial divorcee named Sarah Sorkin (Julia Duffy), that Miles is a dangerous opponent. Miles is shown to be obsessed with his teeth and is constantly cleaning them and brushing them in a bid to have them spotless white.

After Marylin and her lawyer, Freddy Bender (Richard Jenkins), fail to reach a settlement with Miles and Rex (Freddy demands at least the Primary residence and 30% all financial assets), Miles asks Marylin to dinner, where they spar. Marilyn says that she has invested 5 years of her life in Rex and now about to nail him down in court. Marilyn says that divorce means money to her, which means independence.

While they are out, Gus breaks in and copies her address book for Miles, who has his assistant search among the names for Marylin's accomplice in arranging predatory marriages. In court, Marylin feigns an emotional breakdown over Rex's infidelity, professing that she loved Rex unconditionally at first sight. Miles has a concierge named Heinz the Baron "Puffy" Krauss Von Espy (Jonathan Hadary) take the stand. Puffy testifies that Marilyn was a regular at the resort. 5 years ago, Marylin asked him to find her a marriage target who was very rich, foolish, easily controlled, silly and a philanderer whom she could easily divorce, and that he pointed her to Rex. The divorce is granted, but Marylin gets nothing. Marilyn has to move in with her friend Sarah as she has no place else to go.

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. Marilyn asks Donovan for a name. Soon after, Marylin shows up at Miles's office with her new fiance, an oil millionaire named Howard D. Doyle (Billy Bob Thornton). Howard has a tendency to talk too much and has a Texan accent. Marylin insists Doyle sign the Massey Prenup, which will make it absolutely impossible for her to claim any of her fiance's assets in the event of a divorce. Doyle 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 Herb Myerson (Tom Aldredge) 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). Miles then learns that Marylin's ex-husband Rex has died without changing his will, leaving her his entire fortune. Since she is now the wealthier of the two parties, his assets are no longer at risk. 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 (Paul Adelstein) 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 reveals that to get Donaly's help for supplying Howard, she gave him an idea for a hit TV show, restoring his fortunes in the process: America's Funniest Divorce Videos, with Gus as the host.