The 20 Messiest Celebrity Divorces of All Time, Ranked

  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.
·16 min read
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.

As the classic song says, "breaking up is hard to do." And that was definitely the case for the stars listed here. While divorce is incredibly difficult for anyone, these celebrity divorces played out in public, meaning that fans knew about all the cheating scandals, custody agreements, settlement payouts, and other general messiness. When actors fell in love on set and left their spouses behind, the world followed along—whether that meant Elizabeth Taylor and Richard Burton working on Cleopatra or Brad Pitt and Angelina Jolie on Mr. and Mrs. Smith. When exes trashed each other in the press, we were reading every word.

Still, you may have forgotten just how complicated some of these splits ended up being. So read on to find out about 20 of the messiest divorces the celebrity world has seen, from rock stars to literal royalty.

20

Heidi Klum and Seal

Supermodel Heidi Klum and singer Seal split in 2012 after seven years of marriage. They released a statement saying that it was amicable and that they "continue to love each other very much," but there was a hiccup in the process. As reported by ABC News, when it came out that Klum was seeing her bodyguard, Seal told TMZ, "Whilst I didn't expect anything better from him [the bodyguard], I would have thought that Heidi would have shown a little more class and at least waited until we separated first before deciding to fornicate with the help, as it were." Klum's rep then said that it was "sad that Seal has to resort to false accusations," and Seal clarified in statement that he didn't mean Klum cheated, just that they were still legally married.

19

Jennifer Garner and Ben Affleck

Jennifer Garner and Ben Affleck's divorce is one that had both partners seemingly staying on good terms, but was drawn out for quite sometime and included some memorable moments. Before they even split, there was Affleck's awkward 2013 Oscars speech when Argo won Best Picture and he called their marriage "work."

In 2015, the couple announced that they were separating after 10 years of marriage. Then, after a rehab stay for Affleck, rumors of a possible reconciliation, and a headline-making trip with his children's nanny and NFL quarterback Tom Brady, they filed for divorce in 2017. During the separation, Garner gave an interview to Vanity Fair in which she talked about Affleck's giant phoenix back tattoo and famously said, "You know what we would say in my hometown about that? 'Bless his heart.' A phoenix rising from the ashes. Am I the ashes in this scenario? I take umbrage. I refuse to be the ashes."

RELATED: Ben Affleck Just Shared Rare Photos of Ex Jennifer Garner and Their Kids.

18

Tom Cruise and Katie Holmes

Tom Cruise will be mentioned twice on this list, but let's start with his marriage to Katie Holmes, which lasted from 2006 to 2012. Holmes and Cruise made numerous headlines throughout their relationship with everything from him jumping on Oprah's sofa to sharing the first photos of their baby on the cover of Vanity Fair. The divorce itself was settled surprisingly fast, in just 11 days. But, while it wrapped up quickly, questions about the split remained for years—particularly, whether the rumor was true that part of the agreement was that Holmes couldn't date publicly for five years. There was also the fact that Cruise admitted during his tabloid court case that Holmes said one of the reasons she left him was to keep their daughter away from Scientology, as reported by ABC News.

17

Gwen Stefani and Gavin Rossdale

Singers Gwen Stefani and Gavin Rossdale had been together for 20 years welcomed three children when they split up in 2015. At the time, it was alleged that Rossdale had cheated on Stefani with their kids' nanny. Though neither he nor Stefani addressed the claim directly, Us Weekly reported that Stefani found out Rossdale cheated when a different nanny found intimate photos and texts on the family's iPad. Following the split, Stefani released the song "Used to Love You" that was clearly about the demise of the relationship and includes the lyrics, "I don't know why I cry/But I think it's cause I remembered for the first time/Since I hated you/That I used to love you."

16

Madonna and Guy Ritchie

After Madonna married her second husband, director Guy Ritchie, in 2000, they welcomed two sons and Madonna adopted a surprising English accent, but things came to an end in 2008. When the divorce was announced, rumors abounded about their relationship. It was rumored that Madonna cheated on Ritchie with baseball player Alex Rodriguez, that their careers were the cause for the split, and that their were issues due to Madonna practicing Kabbalah. When the divorce was finalized, Ritchie received between $76 and $92 million, according to Reuters.

In the years since, both Madonna and Ritchie have spoke out about the relationship. In an interview with Details (via HuffPost), Ritchie said, "I enjoyed my first marriage. It's definitely not something I regret … But you move on, don't you? You're right, I stepped into a soap opera, and I lived in it for quite a long period of my life." Madonna told The Sun (via Hello!), "There were times when I wanted to express myself as an artist in ways that I don't think my ex-husband was comfortable with. There were times I felt incarcerated."

15

Tom Cruise and Nicole Kidman

Cruise's first marriage was with Nicole Kidman and their split is commemorated now through an image that's since gone viral online. The photograph shows Kidman leaving her attorney's office when the divorce was finalized, looking ecstatic and throwing her arms up into the air.

No one else knows exactly what Kidman was thinking at the time, but what we do know is that she and Cruise were married from 1990 to 2001 and adopted two children together. Cruise filed divorce papers first, followed by Kidman, and they had differing accounts of what happened. Kidman's filing said that she was shocked by Cruise filing in the first place and that she had wanted to work on the marriage. Cruise's filing said that they were split up at an earlier date than Kidman was aware of. There were rumors that the split was due to Cruise being a devout Scientologist. As reported by ABC News at the time, a lawyer for Cruise said, Kidman "has always known exactly why the parties are divorcing." In the end, the kids were raised by Cruise as Scientologists.

14

Elizabeth Taylor and Richard Burton

If you know anything about Elizabeth Taylor and Richard Burton's relationship, it's likely that they were married twice and divorced twice. The first time they got together, it was when Taylor left her husband, Eddie Fisher, for Burton (more on Fisher to come) and Burton left his wife, Sybil Williams, after they met on the set of Cleopatra. They were married for 10 years the first time, but after creating a scandal due to the way they got together, they also became known for their fights and heavy drinking. They got married again in 1975—a year after their first divorce—but divorced again a year later. Burton once said of the relationship (via Biography), "Elizabeth and I lived on the edge of an exciting volcano. I'm not easy to be married to or live with. I exploded violently about twice a year with Elizabeth. She would also explode. It was marvelous. But it could be murder."

13

Jennifer Aniston and Brad Pitt

There is perhaps no Hollywood divorce that has been more talked about than that between Jennifer Aniston and Brad Pitt. The couple split up in January 2005 after five years of marriage, and their divorce was finalized that same year. But while the divorce might not have been a dragged out affair, the story surrounding their split was—and continues to be. Aniston and Pitt split after Pitt met Angelina Jolie on the set of Mr. and Mrs. Smith. While Pitt and Aniston said in a statement that their "separation is not the result of any of the speculation reported by the tabloid media," it came out later that Pitt and Jolie did start falling for each other while filming. Aniston also commented on being bothered by the way Pitt was flaunting his new relationship in an interview with Vanity Fair. But, while Pitt and Aniston are on good terms, this divorce remains one for the ages simply because people still can't get over it.

12

Sandra Bullock and Jesse James

Sandra Bullock divorced her husband of five years, Jesse James, when multiple women came out to say that they had affairs with him. In 2017, seven years after the split, James told the Daily Mail, "Yeah, I did cheat on my wife, yeah, I stood up and took accountability for it and apologized. And that's end of story." He added, "In general, both women and men cheat. It's part of life."

James and Bullock were in the process of adopting a child when they broke up, and the actor went on to adopt her son, Louis, on her own. "My life went the way it went because it was supposed to be that way," Bullock told the Independent in 2018. "Sometimes you have to open up your mind and wait. I can say that, because I see the bigger picture, but when you're in it, you're like: 'When is my family coming?' I was there. I know what that feels like. And at some point you almost let go of the idea, and when you do, all of a sudden the universe goes: 'Oh, you finally let go? Here you go. This is it.'"

For more celebrity news delivered right to your inbox, sign up for our daily newsletter.

11

Kelsey Grammer and Camille Grammer

Kelsey and Camille Grammer got married in 1997, and according to him, there were issues from the start. "I think what I was trying to do was sell it to myself" he said of the relationship on Piers Morgan Tonight in 2011 (via The Hollywood Reporter). "There was this … small voice in the back of my head saying, 'This isn't going to work.' But I stuck to it." The couple went on to appear on the first season of The Real Housewives of Beverly Hills together, which Kelsey called his "parting gift" to Camille. "It was my way of saying, 'Look, you always wanted to be famous. Here you go.'" He also accused her of marrying him because he was Frasier on the successful sitcom. On top of that, Kelsey began seeing his current wife, former flight attendant Kayte Walsh, in 2010 before splitting from Camille.

10

Khloé Kardashian and Lamar Odom

Reality star Khloé Karadshian and former NBA player Lamar Odom had a lengthy separation due in part to Odom's near-death experience. The couple married in 2009 after dating for one month. After four years of marriage and starring in a reality series together, Kardashian filed for divorce in 2013. But, two years later, the divorce papers still hadn't been signed by a judge when Odom went into a coma after experiencing an overdose. At this point, Kardashian withdrew the divorce filing, so that she could make medical decisions for her husband. The divorce was then finalized in 2016.

After they were officially divorced, Odom revealed that he was using secretly using drugs during the marriage and that he had cheated on Kardashian. "I wish I could have been more of a man," he told People. "It still bothers me to this day. But regret is something we have to learn to live with."

9

Eddie Cibrian and Brandi Glanville

This divorce and the next one are all part of the same mess of a love square. Actor Eddie Cibrian and model-turned-reality-TV-star Brandi Glanville were married from 2001 to 2010 and had two children together. The reason they split up was because Cibrian had been unfaithful, including with his current wife, singer LeAnn Rimes. Cibrian and Rimes met on the set of the Lifetime movie Northern Lights. Glanville said in a statement to Us Weekly, "Eddie and I have decided to take some time apart. I want to do what is best for our children [Mason and Jake]. Eddie and LeAnn deserve each other."

Making things even more complicated was the fact that Cibrian also cheated with Scheana Marie. Glanville confronted Marie about the accusation on her show The Real Housewives of Beverly Hills and spoke often about her distaste for Cibrian and Rimes. Marie went on to star on the Real Housewives spinoff, Vanderpump Rules.

8

LeAnn Rimes and Dean Sheremet

Rimes was also married at the time of the affair with Cibrian. She had been married to her husband, dancer Dean Sheremet, since 2002. She admitted publicly to cheating in a 2010 interview with People. "I did one of the most selfish things that I possibly could do, in hurting someone else," she said. I take responsibility for everything I've done. I hate that people got hurt. But I don't regret the outcome." As for Sheremet, he went on to be very open about the split and all the issues he experienced in the marriage.

7

Alec Baldwin and Kim Basinger

Kim Basinger and Alec Baldwin were married from 1993 to 2002 after meeting on the set of the movie The Marrying Man. The divorce process was lengthy as they tried to work out a custody arrangement for their daughter, Ireland Baldwin. ABC News reported in 2008, "There are hundreds of documents, 91 court proceedings so far, and about $3 million in legal costs." In 2007, a voicemail from Baldwin to Ireland in which he called her a "rude, thoughtless little pig" made headlines. At the time of the split, Basinger's father spoke to People magazine and said Baldwin had an anger issue. In a 2016 interview with Porter, Basinger said she and Baldwin were "cool," but also said, "Divorce is hard on a kid, no matter how you cut it. And ours was very public and nasty."

6

Arnold Schwarzenegger and Maria Shriver

PLEASANTON, CA - OCT 4: Arnold Schwarzenegger, Maria Shriver at the CA Comeback Express Bus Tour in Pleasanton, CA on October 4, 2003.
PLEASANTON, CA - OCT 4: Arnold Schwarzenegger, Maria Shriver at the CA Comeback Express Bus Tour in Pleasanton, CA on October 4, 2003.

Arnold Schwarzenegger and Maria Shriver had been married for 25 years and raised four children when she filed for divorce in 2011. The split came after it was revealed that Schwarzenegger had fathered a child with a member of their household staff over 10 years earlier. As reported by Us Weekly, Schwarzenegger said in a statement, "I understand and deserve the feelings of anger and disappointment among my friends and family. There are no excuses and I take full responsibility for the hurt I have caused. I have apologized to Maria, my children and my family. I am truly sorry." While the filing was a decade years ago, the former couple have reportedly not finalized the divorce yet.

5

Kim Kardashian and Kris Humphries

Kim Kardashian and Kris Humphries' marriage is famous for how short it was–only 72 days—but the divorce itself took much longer. The divorced was finalized a year and a half after Kardashian filed. But, while Kardashian wanted a divorce, Humphries argued that the marriage should be annulled. He claimed the marriage was a fraud and that Kardashian used him for her reality show. He also requested $7 million. Eventually, the NBA player dropped this argument and the divorce was finalized with neither having to pay the other any money. During the time of the divorce, Kardashian began her relationship with future husband Kanye West and became pregnant with their daughter, North.

4

Christie Brinkley and Peter Cook

When supermodel Christie Brinkley's divorce from architect Peter Cook was finalized, the New York Daily News called it "one of New York's nastiest divorce battles." During the trial, Cook had to admit that he cheated on Brinkley with an 18-year-old assistant, paid her $300,000 to keep quiet, and was spending $3,000 on explicit internet sites. "I was devastated, and I was in this emotional tug of war where I was discovering more and more every day," Brinkley said in court, according to ABC News. "It was a nightmare…Anyone who would chase a teenager, a young girl, I mean, where is his judgment?" In the end, Brinkley was given sole custody of their two children while Cook had visitation rights.

RELATED: Christie Brinkley's 22-Year-Old Daughter Looks Exactly Like Her.

3

Debbie Reynolds and Eddie Fisher

Here's another old Hollywood one for you. Eddie Fisher and Debbie Reynolds' divorce was messy, because Fisher left Reynolds for another woman: Elizabeth Taylor. Taylor, Reynolds, Fisher, and Taylor's husband, Mike Todd, had all been close friends—so close that Reynolds and Fisher were in Taylor and Todd's wedding as the matron of honor and best man. Reynolds and Fisher also named their son after Todd. But, after Todd died in a plane crash, Fisher and Reynolds found comfort in each other to the point that Fisher ended up leaving Reynolds for Taylor a month later. A year after that, Fisher and Taylor got married.

2

Tiger Woods and Elin Nordegren

Tiger Woods went from being known as one of the greatest golfers of all time to being covered endlessly in the media for a much more scandalous reason in 2009. It was revealed that Woods had numerous affairs during his marriage to Elin Nordegren with whom he shares two children. In February 2010, he admitted to his actions to a group of reporters. "I was unfaithful, I had affairs, I cheated," he said (via the Guardian). "What I did is not acceptable and I am the only person to blame. I stopped living by the core values I was taught to believe in. I knew my actions were wrong but I convinced myself that normal rules didn't apply."

During the scandal—which also involved Woods crashing his car in his front yard and a rumor that Nordegren attacked him with a golf club (which she denied)—he took a break from golf, entered a program, and eventually, split from his wife. Nordegren and Woods' divorce was finalized in August 2010 after six years of marriage.

1

Princess Diana and Prince Charles


Prince Charles and the women then known as Diana Spencer were doomed from the start. Even before they got married, Charles and Diana gave an awkward interview in when they was asked if they were "in love" and Charles responded, "Whatever 'in love' means." When the pair got married in 1981, Charles still had feelings for his ex, Camilla Parker Bowles (to whom he is now married), and they began an affair in 1986. Around the same time, Diana began having an affair of her own. In 1992—after an in-depth biography of Diana came out that detailed her marriage issues and eating disorder, and an explicit phone call between Camilla and Charles was released—Charles and Diana separated. It was four more years until they divorced, during which time Charles admitted to cheating and Diana gave a tell-all interview in which she said there were "three us us in this marriage." When your divorce threatens the monarchy, leaving reverberations that are still felt today, it has to be number one on the list.

RELATED: 27 Celebrity Couples With Huge Age Gaps.