The 5 Nastiest Celebrity Divorces Of All Time

Breaking up is hard to do, especially for the rich and famous.

The 5 Nastiest Celebrity Divorces Of All Time Kathy Hutchins / Shutterstock

Marriage is hard work, we know, but sometimes a couple can put everything they have into making their relationship work, and it still goes bad. And then it gets worse, when it comes time to divide up kids, pets, and that signed vintage copy of Thriller that you swear was originally yours.

It turns out that Hollywood's famous faces really are just like us. Famous people's divorces are nasty, mudslinging affairs, but damned entertaining ones.


1. Amy Winehouse & Blake "Incarcerated" Fielder-Civil

It's always a shame when a marriage built on mutual addiction goes awry. But awry it went: Amy and Blake had only been married four months when she first contemplated leaving him, back in September 2007. Rumors of his cheating and that he married her for her money had dogged the relationship, and Blake reportedly threatened to kill himself if she left him, so the marriage limped on through his jail sentence for "perverting the course of justice" — that is, he tried to bribe a guy he assaulted not to press charges. 

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The pair held a jailhouse vow renewal in January 2008, but when he was released from prison in February 2009, Blake declared he wanted a divorce. And then he promptly knocked up a junkie (who wasn't Amy) and demanded $9 million from Amy for inspiring her Back to Black album — by dumping her. Their split was mercifully finalized by a UK court, and thank Jebus for it, because every single thing Amy and Blake do makes our heads hurt. Winehouse tragically passed away in July 2011.

2. Kate Walsh & Alex Young

The Private Practice star married the Fox executive in 2007 after five months of dating, and they were happy for, like, a minute. Alex filed for divorce and put our pretty, pretty Kate through hell for months. He had accused her of hiding financial information (California, remember, is a community-property state, and it appears the two didn't have a prenup) and of refusing to provide a full accounting of joint assets, that is, the house they bought in August 2007.

He even went so far as to subpoena the head of ABC Television, Steve McPherson, you know, Kate's BOSS, to demand that McPherson testify about Kate's future earning potential. 


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3. Christie Brinkley & Peter Cook

The supermodel and ex–Mrs. Billy Joel married Cook, an architect, in 1996. They had a daughter, Sailor, in 1998, and he adopted her son from a previous marriage. And then it all went to hell. Christie filed for divorce in September 2006, two months after reports broke that the then 47-year-old Cook had been sleeping with an 18-year-old employee. Christie fought savagely to have the case open to the media, and oh, was it ever.

When the case finally went to trial in the summer of 2008, their two kids were only the smallest of those with a front-row seat to the jurisprudential warfare. Christie's lawyer at one point described Cook as a "self-obsessed sex addict who spent thousands of dollars on Internet porn years before he began wooing a 17-year-old girl," according to Slate. The case was eventually, finally, settled when all the combatants collapsed of exhaustion. Cook is now dating 21-year-old Alba Jancou.


4. Charlie Sheen & Denise Richards

She probably should have known better. Sheen already had a reputation as a sleaze and patronizer of hookers before he married the one-time Bond girl/nuclear physicist in 2002. Denise filed for divorce the first time in March 2005, while she was pregnant with their second daughter, Lola, but they reconciled.

She filed again in 2006 and later secured a restraining order against Sheen, on the basis of death threats and his abiding relationship with porn and prostitutes. The split was finalized in November 2006.

5. Paul McCartney & Heather Mills

When a heartbroken Cute Beatle married the former model and anti-landmine activist a few years after the death of his wife of 29 years, Linda, many, many people, including his daughter, Stella, screamed "Rebound gold-digger!" And they were right. Paul and Heather had a daughter, Beatrice, in 2003, but things did not stay happy.


He filed for divorce in July 2006 and the flinging of mud began. Heather accused Paul, among other things, of violent behavior and failing to protect her from tabloid scrutiny (really!), which everyone who'd ever met the man had a hard time believing. They went to court in February 2008 and even the judge started to hate Heather. The miserable episode ended with Heather getting $50 million and everyone else, including Paul, getting to forget about her.

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Sara Brady is a freelance writer and editor living in Manhattan. She attended the College of William & Mary and enjoys strong coffee, college football, runny cheese, movies involving explosions, semicolons, and British bands with loads of guitars.

Editor's Note: This article was originally posted on July 24, 2009 and was updated with the latest information.