Celebrity Couples That Filed For Divorce Multiple Times

There's an old adage that goes, "If at first you don't succeed, try, try again." The line is usually tossed out when someone is facing a setback — a failed job interview, a missed goal, a dropped ball — but that's not technically the only way it can be used. Just ask these celebrities, who applied it to their failing relationships.

All of the famous couples on our list have filed for divorce from each other more than once. Some of them have simply withdrawn their petitions and attempted to reconcile, while others have actually gone through with their divorces only to change their minds and get remarried. Sometimes, they've found enough happiness in the second go-round that they stayed together for years (or even decades), while other pairings managed to only eke out a few more months of wedded bliss before throwing in the towel. 

While there are countless reasons people file for divorce, with some of the most common being adultery, financial woes, or the oft-cited irreconcilable differences (via Today), it might not be as uncommon as you'd think for married pairings to try, try again after talks of divorce are on the table: According to Divorce Statistics, 87% of couples who separate end up going through with divorce — meaning that 13% end up reconciling. Regardless of the ultimate outcome of these reunions, there's no denying that the following multi-divorce stories are wildly interesting. These are the celebrity couples that filed for divorce multiple times.

In 1991, before "Achy Breaky Heart" made him a household name, aspiring musician Billy Ray Cyrus lived in his car and hung out at clubs on the weekend. It was in one of these Nashville hot spots that he met his future wife, Tish Cyrus. In 1992, the couple welcomed their first child together, future superstar Miley Cyrus — and a year later, they tied the knot in the living room of their Franklin, Tennessee home. The duo soon added two more children to their blended brood (both parties had kids from prior relationships), and eventually split time between The Volunteer State and Los Angeles, where Billy Ray and Miley filmed their Disney Channel hit "Hannah Montana."

The series' success and family focus tricked many fans into believing the Cyruses were just as happy off-screen as they appeared on-screen. In reality, Billy Ray told GQ of "Hannah Montana," and the fame that came with it, "The damn show destroyed my family." He and Tish filed for divorce in 2010, but reconciled mere months later in 2011, with Billy Ray telling "The View" (via People), "I want to put my family back together." Unfortunately, the peace didn't last long, and Tish filed for divorce again in 2013 and April 2022.

It seems likely that the pair's separation would stick the third time around. Although Billy Ray and Tish made it clear in a statement to People that their amicable decision was made "with love in our hearts," TMZ cited court documents which revealed they'd been living separately since at least 2020.

Megan Fox has never seemed too concerned with how her life appears in the tabloids, and her relationship with ex-husband Brian Austin Green might just be perfect proof of that. The pair met on the set of "Hope & Faith" when Fox was just 18 and Green was 30. As Fox revealed in an interview with Elle, "I had to convince him that I was slightly more responsible and well-spoken and had other things to bring to the table besides being 18." Eventually, the bombshell won him over, and in 2006, the pair got engaged. They briefly called things off in 2009 but got back together and married the following year.

In 2015, ET reported that Fox had filed divorce papers, citing "irreconcilable differences." But when the estranged couple got pregnant with their third child several months later, they reconciled once again. However, it seems expanding their brood ultimately didn't heal their fractured relationship, and Green confirmed that they had called it quits once again on his "...With Brian Austin Green" podcast in 2020. Just weeks after Fox announced her engagement to rapper Machine Gun Kelly in January 2022, her divorce from Green was finalized. That February, Green revealed that he and girlfriend Sharna Burgess were expecting their first child together. 

"As long as they're both on the same page with the kids, he's good and happy for her," a source told People of the amicable exes around this time. "They're strictly co-parents." With that, one of the hottest couples from the mid-2000s was officially a thing of the past.

In 2007, Pamela Anderson announced that she was engaged to an unnamed professional poker player — a little digging by the press revealed the man to be none other than Rick Salomon, Paris Hilton's ex-boyfriend and co-star in her leaked sex tape. It's unclear how long these longtime friends had been dating, but that October, Anderson and Salomon quietly married at the Mirage Hotel in Las Vegas.

The wedding was reportedly a simple affair, squeezed into a break Anderson had between her magic shows. However, according to a source cited by People, it appeared to be exactly what the loved-up couple wanted — or at least, what they thought they wanted. Within months, Anderson cited fraud when asking a judge to annul the marriage. She'd previously cited irreconcilable differences when filing to dissolve their brief union that December, but called off the divorce in the hopes of reconciliation. TMZ reports that her second request to the court was granted, and the two went their separate ways ... sort of.

Joking that she was "recycling" significant others during a 2013 appearance on "The Ellen DeGeneres Show," Anderson admitted that she and Salomon were "best friends ... with benefits" (via E! News). In January 2014, they went from FWB to husband and wife, with Anderson stating of round two, "We're very happy ... and that's all that matters." Six months later, Anderson and Salomon filed papers to once again become ex-spouses, temporarily called the split off, and re-filed for divorce in early 2015. This on-and-off pairing was officially over that April.

In the '60s and '70s, Elizabeth Taylor and Richard Burton were undeniably the most glamorous couple in Hollywood. They were also arguably one of the most dramatic. Sparks flew when the duo began filming "Cleopatra" in 1962, during which their on-screen kiss lingered far longer than the scene required, per Vanity Fair. Their clear interest in one another wouldn't have been an issue, except for the fact that they were both married to other people. They didn't let that stop them, and 1964 saw the pair tie the knot in Montreal, shortly after Tayor finalized her divorce from fourth husband Eddie Fisher, according to Woman's Day.

They spent the next decade shooting films together (they co-starred in 11 in total), welcoming four children, traveling the world, and making tabloid headlines with reports of their frequent fights, affairs, addictions, and that infamous 33.19-carat diamond. All that drama eventually proved too much, and in 1974, Taylor and Burton divorced. Their separation didn't last long, however. Their short-lived second attempt at happily-ever-after came the following year, when the two remarried in Botswana, but they divorced in 1976.

Not being the type to let a good thing go, Burton and Taylor weren't satisfied with completely going their separate ways post-divorce No. 2. Their ongoing friendship frequently ignited speculation that they were on the verge of reconciling for a third time. In fact, rumor has it that the last letter Burton wrote Taylor before his death in 1984 expressed a desire to be reunited with her once and for all.

In 1972, a 14-year-old Melanie Griffith met her future husband, Don Johnson, for the first time. The young actors were filming "The Harrad Experiment" together. However, Johnson was eight years Griffith's senior, and Tippi Hendren — aka Griffith's mom, who also happened to play the movie's female lead — had some understandable concerns about the age gap. She later told The Hollywood Reporter how she panicked upon realizing her teenage daughter's attachment to Johnson — despite this, the couple began a relationship almost immediately, moving in together the following year, and getting engaged once Griffith turned 18. Per People, 1976 saw them marry in Las Vegas.

Their already tumultuous relationship, thanks to Johnson's many admitted affairs and both parties' budding alcohol and drug addictions, didn't get any easier after exchanging vows, and they divorced six months later. Fast forward to 1989: The couple reconnected when Griffith phoned her then-sober ex for moral support ahead of going to rehab, which led to the pair rekindling their connection. They tied the knot for a second time at their ranch in Aspen that June, and soon welcomed their famous daughter, Dakota Johnson. "I believe some relationships are fated, and ours was probably one of them," Griffith told People. "I'll always love him. He was my first love."

But by 1994, the "50 Shades of Grey" star's parents had both relapsed on their sobriety, and Griffith filed for divorce that March, citing irreconcilable differences (via the Los Angeles Times). She and Don Johnson have since remained amicable exes.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Tesla billionaire Elon Musk's on-again-off-again relationship with Grimes has been ideal tabloid fodder since the pair went public with their love in 2018. However, theirs isn't the only romantic relationship the South African business magnate has seen splashed across headlines. In 2008, after initiating his divorce from his first wife, Justine Musk, Elon began dating British actress Talulah Riley. According to an interview Justine gave Marie Claire, Elon texted her six weeks after their divorce was finalized to let her know he was engaged to his new girlfriend. In 2010, not long after that text was sent, Musk and Riley got married.

Then, in 2012, they divorced for the first time. In a now-deleted tweet, Musk demonstrated just how amicable the whole thing was, writing (via Page Six), "It was an amazing four years. I will love you forever. You will make someone very happy one day." The sweet sentiment hit different when, 18 months after their initial divorce was finalized, the couple headed back down the aisle.

Unfortunately, that second round of happiness wouldn't last long, and Musk filed for divorce again in 2015. In the filings, he agreed to give Riley $16 million in cash as a part of a financial settlement, as well as all of the property their pre-marital agreement entitled her to. However, he never ended up paying that money out, as they called off the divorce seven months later. It wasn't until 2016, when Riley filed for divorce, that they'd actually end their relationship for good.

Academy Award-nominated actor and "Empire" star Terrence Howard may have a robust filmography, but his relationship history is decidedly less acclaimed. Howard married his first wife, Lori McCommas, back in 1989. The couple had three children together, two daughters and a son, and lived a relatively quiet life until 2001. That year, Howard was arrested on disorderly conduct charges after hitting McCommas during an argument. The assault caused quite the scandal, and, years later, Howard would openly admit to the abuse, telling Rolling Stone, "She was talking to me real strong, and I lost my mind and slapped her in front of the kids. Her lawyer said it was a closed fist, but even slapping her was wrong."

The incident seems to be a fairly solid indicator of how things were going between the couple, because shortly thereafter, in 2003, they divorced. In 2005, Howard and McCommas shocked everyone when they quietly remarried. But by 2007, the honeymoon was over and the couple once again went their separate ways.

McCommas isn't the only ex-wife Howard has gone back to, either. In 2013, Howard married restaurateur Mira Pak. They divorced in 2015, but remained close and got engaged again in 2018. As of this writing, they haven't made their relationship legally binding, but if they ever do, it would open up the door for Howard to become a serial multiple-divorces-from-the-same-woman offender.

If you've ever listened to a single Eminem song, you know the rapper's life has been tumultuous. His relationship with ex-wife Kimberly Scott is a perfect example of this. In the book "How Eminem Got Started" (which is endorsed by Marshall Mathers himself), author Ramses M. reveals that the rapper first met Kimberly Scott back in 1988, when he was 15 and she was just 13. Later that year, Kim moved in with Eminem and the couple began the toxic on-again-off-again relationship they'd share for the next decade. In 1999, four years after their daughter was born, Eminem and Kim tied the knot for the first time.

The marriage didn't last long — both parties had volatile tempers, struggled with addiction, and, according to Kim who gave an interview to "20/20" in 2007, Eminem was regularly being unfaithful. In 2000, Eminem requested a divorce for the first time, but when Kim hit back with an emotional distress lawsuit, they called the whole thing off. A few months later, in early 2001, Kim, seemingly having had a change of heart, submitted her own divorce request, and their first union officially ended later that year.

The duo remained in touch as they co-parented their daughter, and in 2006, Eminem's representative told People the couple had remarried. Fans were hopeful things would work out this time around. as both Kim and Eminem were older and wiser, but less than three months later, the rapper had filed divorce papers for a second time.

Soul singer Dionne Warwick's career is nearing the end of its seventh decade (her first performances, as a member of The Drinkard Singers, took place in the mid-'50s), making her one of the most successful female vocalists of all time. While her career has been legendary, her romantic relationships have had far less staying power. In 1966, just as her solo career was taking off, Warwick married an actor and drummer named William Elliot. Their first attempt at marriage only lasted about a year, and by May 1967, they had gone their separate ways. However, seemingly realizing they had thrown in the towel a little too easily, the couple remarried in August 1967, remaining together until 1975.

In a 2020 interview with The Guardian, Warwick revealed the reasons for her multiple divorces, saying, "I was the major earning power in the family and that is very difficult for the male ego. It just got too much to bear for my husband, and we decided that it would be best for us to part ways." Despite never reigniting their romantic relationship, Warwick and Elliott remained close for the sake of their sons, David and Damon. What more can you really ask for from a couple who gave love a shot not once, but twice?

As of 2022, rocker Travis Barker may be happily married to Kourtney Kardashian, but his previous relationship with former Miss USA Shanna Moakler wasn't nearly as joy-filled. According to Life & Style, Barker met Moakler in 2002. A year after the relationship began, Barker proposed to his girlfriend on the Haunted Mansion ride at Disneyland, and a short while after that, they tied the knot in a "The Nightmare Before Christmas"-themed wedding. Things were good for a while; the couple welcomed two children of their own and were happily raising them alongside Moakler's daughter from a previous relationship. But in 2006, it seemed the good times were over when Barker filed for divorce for the first time.

Of course, as is the case with all of the couples on our list, the relationship didn't end that easily. The couple attempted to work things out and reconciled a number of times, even going so far as to withdraw their divorce application after the plane crash Barker was involved in back in 2008. Ultimately, they decided they just weren't going to be able to make things work and finalized their divorce later that year. While the separation started out amicably, things got dramatic when the couple began accusing each other of laziness and infidelity on MySpace and through tabloids like TMZ. It likely didn't help that they were living in the same house (for the sake of their children) while trying to move on from the relationship. Maybe it's just us, but that doesn't seem like the easiest way to heal.