Miles Massey (Intolerable Cruelty) is the top divorce attorney in the United States. Massey is also the inventor of the “Massey Prenup.” The Massey Prenup is a prenuptial agreement which has never been successfully challenged., so no party to it can benefit financially in the event of divorce.

Miles admits that to his associate Wrigley that he is in the middle of a mid-life crisis, and he is feeling very bored with his life. He compares himself to Attila the Hun, Ivan the Terrible, and Henry the VIII, all of whom destroyed their opponents in entirety. Miles feels that he has done everything, seen everything, bought everything, and therefore he is seeking the ultimate challenge.

Massey is hired by Bonnie Donaly after Bonnie’s husband, Donovan, finds Bonnie in a compromising position with a pool cleaner. Massey assures Bonnie he will win the divorce case for her and leave Donovan with nothing.

Miles also advises Rex Rexroth, who was caught on camera with a woman other than his wife. Massey assures Rex that despite his wife Marylin’s joy at the possession of the tape as her ticket to wealth and a way out, Miles will win the divorce case. Marylin is warned by her girlfriend, Sarah Sorkin, to be wary of Miles Massey.

Miles, Rex, and Wrigley fail to agree with Marylin and her lawyer Freddy Bender on the divorce settlement, so Miles asks Marylin to dinner. Apparently Miles decides that Marylin Is the challenge he’s been looking for.

After more investigating, Miles reveals that Marylin has been planning and calculating for years, having told Heinz aka the Baron Krauss von Espy, that she was looking for a rich husband who could be easily manipulated. Because of this surprise witness, Miles wins the case for Rex, leaving Marylin with nothing.

Marylin vows her revenge on Miles, and contacts Donovan Donaly, who is now living on the street, to help her, while Miles receives hearty congratulations and praise from his boss for his fine work.

Soon after the divorce hearing, Marylin shows up to Miles’ office with her new hubby-to-be, Howard D. Doyle. The two sign the Massey Prenup, though Doyle later destroys it as a sign of affection for Marylin. Marylin takes the fortunate change of circumstances and divorces Howard, leaving her with an abundance of wealth.

Months later, Miles and Marylin cross paths at a convention in Las Vegas. The convention is for divorce attorneys. The two realize how lonely they are, despite the wealth they both own. Completely smitten with Marylin, Miles and Marylin marry on the spur of the moment. Miles makes the decision to stop doing divorce suits and do pro-bono work instead in east L.A.

Unfortunately for Miles, he discovers that he was the victim of Marylin’s scam this time. Doyle was no millionaire, just as actor in one of Donaly’s soap operas. Marylin has no money of her own, and now Miles’ wealth is vulnerable to Marylin’s greedy claws.

Miles boss is very perturbed by the situation. He demands action because Marylin has humiliated the firm more than enough. The boss hires a hit man, Wheezy Joe, to take Marylin out of the equation for good. However, before the assassination is complete, Miles discovers that Marylin’s ex-husband, Rex, has died and left her millions of dollars. When Miles realizes how much he can benefit from this divorce, he rushes out to try and stop the assassination.

Before Miles runs into Joe, Marylin meets him first. Marylin realizes that Joe is there to kill her, so she pays him double to kill Miles. When Miles then runs into Joe, he sprays him with Mace to defend himself. Joe then accidentally shoots himself in the head, mistaking his gun for his asthma inhaler.

Marylin and Miles meet up a divorce attorney’s office to finish up the divorce. Miles, however, is still madly in love with Marylin and signs a Massey Prenup to show his dedication to her. Marylin tears it up, and the two passionately reconcile. Marylin tells Miles that she pitched a television show idea to Donovan Donaly about divorce, and the movie ends as the first episode of America’s Funniest Divorce Videos airs.

Miles Massey is played by legendary actor and producer George Clooney. Clooney is one of the first mega-stars to star in a Coen Brothers film, along with Paul Newman, Catherine Zeta-Jones, Tom Hanks, and Brad Pitt.