Miles Massey (GEORGE CLOONEY) is probably the best divorce attorney in town. Renowned for his bulletproof pre-nup, he can put a spin on almost any case and end up ruining the lives of innocent people, such as soap opera producer Donovan Donaly (GEOFFREY RUSH) whose wife was cheating on him. With the aid of his associate, Wrigley (PAUL ADELSTEIN), Miles is nearly unbeatable.
That is, until he sets eyes on the ravishing Marylin Rexroth (CATHERINE ZETA-JONES). She recently hired private eye Gus Petch (CEDRIC THE ENTERTAINER) to catch her real estate developer husband Rex (EDWARD HERRMANN) in the middle of an affair. With the aid of her lawyer, Freddy Bender (RICHARD JENKINS), and support from her divorced best friend, Sarah Sorkin (JULIA DUFFY), she hopes to get half of Rex's total worth.
Miles won't have any of that, and goes to some underhanded measures to introduce a surprise client, Heinz, the Baron Krauss von Espy (JONATHAN HADARY), into the divorce proceedings. When that's done, Miles, who's growing nervous about turning into an elderly workaholic like his boss, decides to pursue her.
Yet, she's already found a new suitor in the form of oilman Howard D. Doyle (BILLY BOB THORNTON). With Miles progressively losing control and falling head over heels for Marylin, it's only a matter of time before more weddings, divorces and even a hitman, Wheezy Joe (IRWIN KEYES), further complicate matters.