14 Messiest Celebrity Divorces of All Time
Divorce is hell on anyone, but it might be the one area where celebrities can legitimately claim they have it worse than the rest of us. They have a lot more money to fight over, their pettiest court filings end up online for all the world to see and they have to definitively “win” the breakup with a well-placed cover story about how much the other person sucked. It’s a lot more complicated than going down to the courthouse and filing for a dissolution of marriage.
Celebrity divorces happen all the time, of course—there are at least three major ones in process as of this writing—but only a few of them ascend to a level of fame that outstrips their parties’ lesser work. You’re more likely to know about Angelina Jolie’s winery fight with Brad Pitt than you are to have seen their 2015 bomb By the Sea, for example, just like you’ve probably watched more minutes of Amber Heard and Johnny Depp’s defamation trial than their 2011 collaboration The Rum Diary. As Spider-Man’s uncle once said, with great power comes great responsibility—and great interest in your divorce battle.
Related: The Biggest Celebrity Splits of 2023 (So Far)
Keep reading for a roundup of the messiest celebrity divorces in Hollywood history.
Messiest Celebrity Divorces
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Just three months after Christine Baumgartner threw her husband, Kevin Costner, an adorable belated celebration for his January 2023 Golden Globe win, she filed for divorce—proving that you never really know what’s going on with seemingly solid celeb couples.
Their split quickly turned nasty, with Costner accusing Baumgartner of spending $188,000 per month on plastic surgery. The duo also engaged in a public battle over Baumgartner leaving their shared Malibu home, which reached a nadir when Costner said in legal documents he was worried she would “take too many pots and pans” when she left. Baumgartner ultimately vacated the property in July 2023, but they’re still hammering out arrangements around everything else: finances, property and custody of their kids.
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In their heyday, Kim Kardashian and Kanye West—known to the world as Kimye—seemed unstoppable, but death comes for us all, especially if we’re celebrity super couples landing joint Vogue covers. Kardashian filed for divorce from West in February 2021 after nearly seven years of marriage, citing irreconcilable differences.
At first their split seemed relatively amicable, with Kardashian agreeing to wear a wedding dress during a West concert in August 2021, but things fell apart after West started publicly claiming he wanted her back. He also threatened her then-boyfriend, Pete Davidson, and slammed her parenting style via social media before torpedoing his career with an antisemitic tweet that got him fired from Adidas. They finalized their divorce in November 2022, but it seems highly unlikely that their saga is over.
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After his split from longtime partner Vanessa Paradis, Johnny Depp moved on with Amber Heard, whom he met while filming the 2011 movie The Rum Diary. They married in February 2015, but just over one year later, Heard filed for divorce and claimed that Depp was verbally and physically abusive toward her for the duration of their relationship. Depp denied the allegations, and the duo settled their divorce in early 2017.
That was far from the end of it, though. Depp filed a libel lawsuit against The Sun’s parent company for an article that called him a “wife beater,” and he sued Heard for defamation over an op-ed in The Washington Post where she described herself as a victim of domestic violence. Depp lost his case against The Sun, but a Virginia jury found that Heard defamed her ex-husband and awarded him $10.35 million in damages. Heard, meanwhile, was awarded $2 million for a defamatory statement one of Depp’s lawyers made about her. They both filed appeals but ultimately settled in December 2022.
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Maria Shriver filed for divorce from Arnold Schwarzenegger in July 2011 after 25 years of marriage. Two months earlier, Schwarzenegger publicly admitted that he fathered a child with their household employee Patty Baena in 1997. The former spouses are closer now, but it took them 10 years to finalize their divorce, which Schwarzenegger called “my failure” in a May 2023 interview with The Hollywood Reporter.
Related: Far From Expendable! Arnold Schwarzenegger's Net Worth In 2023 Is Massive
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In 2009, Tiger Woods publicly admitted to cheating on then-wife Elin Nordegren after a car crash near their home kicked off a series of lurid headlines about Woods’ extramarital affairs. Woods completed a 45-day treatment program but lost tons of his golf sponsorships and took a break from sports. The former couple finalized their divorce in August 2010.
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The British royal family is famous for the adage “never complain, never explain”—which Princess Diana ignored when she collaborated with Andrew Morton on the explosive 1992 book Diana: Her True Story. In the book, Diana accused King Charles III (then the Prince of Wales) of having a years-long affair with Camilla Parker-Bowles, whom he dated before meeting Diana. After leaked phone conversations featuring both Diana and Charles made headlines, Prime Minister John Major announced the couple’s separation in December 1992. Then, in 1995, Diana sat down for her now-infamous BBC interview and dropped the line, “There were three of us in this marriage.”
Charles and Diana finally divorced in August 1996, and Charles went on to marry Parker-Bowles—now Queen Camilla—in 2005. Diana died at age 36 in a car crash in Paris in August 1997, just one year after finalizing her split from Charles.
Related: 50 Princess Diana Quotes to Memorialize the People's Princess
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Kelly Clarkson and Brandon Blackstock’s divorce battle didn’t last as long as some celebrity splits, but it became a subject of public fascination thanks in part to the dollar amounts involved. After two years of back-and-forth over custody and assets, Clarkson agreed in March 2022 to pay her ex $115,000 per month for the following two years, plus a one-time payment of $1.3 million. While Clarkson got primary custody of the kids, she also agreed to pay Blackstock $45,000 per month in child support until their two children turn 18. Clarkson eventually processed the whole situation through song, writing about the difficult split on her 2023 album, Chemistry.
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The messiest breakup in Paul McCartney’s life wasn’t the demise of the Beatles—it was his split from Heather Mills, whom he married in 2002. Their relationship was plagued by reports of strife from day one, and after four years, they threw in the towel. After a two-year court battle, McCartney settled with Mills for a cool $50 million. Mills, meanwhile, wasn’t afraid to speak her mind about her ex-husband or his family. In 2007, she claimed her ex’s daughter Stella McCartney tried to “break up” her dad’s marriage “every single week.”
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Days after winning her first Oscar in March 2010, Sandra Bullock woke up to reports that her then-husband, Jesse James, had been cheating on her while she was away filming the movie that won her the Academy Award. James publicly apologized for the affair, but more women came forward claiming they had relationships with him, and in April 2010, Bullock filed for divorce.
James’ problems only continued when a 2004 photo resurfaced that showed him wearing SS regalia and giving a Nazi salute. Bullock, meanwhile, adopted son Louis, whom she’d originally planned to adopt with James. The former couple finalized their divorce in June 2010, citing “conflict of personalities” as the reason for the split.
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Days after celebrating their 10th wedding anniversary in June 2015, Ben Affleck and Jennifer Garner announced their plans to divorce. Counseling sessions and public outings initially made it seem like they might reconcile, but they jointly filed in 2017 after Affleck completed a rehab stay for alcohol addiction. Reports also surfaced that he was having an affair with the couple’s 28-year-old nanny, which he denied. Garner later said that the nanny was “not part of the equation” when it came to the decision to end her marriage. The former couple finalized their divorce in late 2018, and they’ve since remained amicable coparents of their three children.
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Kim Basinger and Alec Baldwin called it quits in 2000 after being married for seven years—the same length of time they spent battling for custody of their only child, daughter Ireland. Basinger and Baldwin are on better terms now, but Baldwin claimed in his 2008 memoir that his ex-wife spent $1.5 million trying to deny him parental rights. Basinger, meanwhile, said in 2022 that her ex-husband was “a challenge.”
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Brad Pitt and Jennifer Aniston split nearly 20 years ago, but their breakup was so legendary that tabloids are still writing stories about whether they get along now—and a vocal corner of the internet is still holding out hope that they’ll rekindle their romance.
While the legal aspect of their divorce was relatively simple—no children, and they finalized in less than a year—their split still lives large because of the circumstances surrounding it. Pitt was rumored to have cheated on Aniston with Angelina Jolie while filming Mr. and Mrs. Smith, in which they played very sexy married assassins assigned to kill each other. Jolie denied hooking up with Pitt before he was divorced, but the idea took hold anyway, spawning “Team Jolie” and “Team Aniston” T-shirts and spectacularly ill-timed W magazine photo shoot.
Aniston, in a 2005 Vanity Fair cover story, then gave women everywhere a new way to describe their trifling exes: “There’s a sensitivity chip that's missing.”
Related: Jennifer Aniston's Net Worth in 2023
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After divorcing Jennifer Aniston, Brad Pitt moved on with Angelina Jolie, whom he’d met while he was still married. Their relationship lasted a long time by Hollywood standards (12 years), but their divorce is also on its way to breaking records—it’s been going on for nearly seven years.
Jolie filed for divorce from Pitt in 2016 after marrying him just two years earlier, and they’ve since been locked in nasty legal battles over everything from custody of their six children to the French winery they formerly co-owned. In one particularly surreal moment, Pitt accused Jolie of choosing Chateau Miraval’s buyer, the Stoli Group, to intentionally damage Pitt’s reputation because its owner, Yuri Shefler, is a Russian oligarch who Pitt claims has ties to Vladimir Putin. (Shefler, who left Russia in 2002, has publicly distanced himself and his company from Putin.)
Jolie has also alleged that Pitt was abusive toward her and her children during the 2016 plane ride that led her to file for divorce. Pitt, for his part, has denied her allegations.
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Charlie Sheen’s “tiger blood” era was so wild that it’s easy to forget he too was once caught in a messy public divorce. In March 2005, his then-wife, Denise Richards, filed for divorce while she was six months pregnant with their youngest daughter, Lola. They briefly reconciled, but Richards filed again one year later. Their divorce was finalized in late 2006, and Sheen was ordered to stay 300 feet away from Richards and their kids except during supervised visits.
The duo are on better terms now, but as recently as 2019, Richards claimed Sheen owed her nearly half a million dollars in unpaid child support. (A judge ruled in 2021 that Sheen no longer had to pay.)
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