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Hollywood romances can be just as complicated as the scripts they star in. Join us as we look back at some of the longest-lasting celebrity marriages that ultimately ended in divorce. From musical legends to Hollywood power couples and reality TV icons, these relationships spanned decades before calling it quits. Find out what led to the splits and how these stars moved on from years of commitment.
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00:00Now to the divorce settlement between Mel Gibson and his wife of 31 years, Robin Moore, the nearly $450 million agreement.
00:08Welcome to Miss Mojo, and today we're looking at Hollywood's longest lasting marriages that eventually ended in divorce.
00:13We'll be excluding couples like Meryl Streep and Don Gummer, however, as although they are separated, they remain legally married.
00:19Even with their problems, the marriage lasted 39 years.
00:24Tony says she finally decided to call it quits in 2014.
00:30Jane Seymour and James Keech
00:32British-American actress Jane Seymour, famous for her roles in Live and Let Die and Dr. Quinn, Medicine Woman, married actor and producer James Keech in 1993 after meeting through mutual industry connections.
00:42Together, they welcomed twin boys John Stacey and Christopher Stephen, who added a family dimension to their busy careers.
00:49However, after years in the spotlight together, the couple decided to part ways, finalizing their divorce in 2000.
00:54I was married for 24 years, and I never thought that was going to end, you know, and that happens to a lot of people.
01:00And it was a major shock to my system and to the whole family.
01:03But, you know, now, two years later, we're very good friends.
01:06We spent Thanksgiving together.
01:07We'll spend Christmas together.
01:09While their marriage ended, both continued to thrive professionally, with Seymour becoming a beloved Hollywood icon and Keech maintaining a successful career in acting and producing.
01:17I'm not stuck in the past.
01:19I'm not regretting anything.
01:21I'm embracing today, and I'm very open-minded about the future.
01:25Kris and Caitlyn Jenner
01:26When Kris Jenner married Olympic gold medalist Caitlyn Jenner in 1991, they became a blended family powerhouse.
01:33Kris brought her four Kardashian kids from her first marriage, and together they welcomed Kendall and Kylie.
01:37The pair's dynamic would later anchor one of the most successful reality franchises ever, turning their family into nothing short of a cultural phenomenon.
01:43The couple eventually separated in 2013 and finalized their divorce in 2015, ending 22 years of marriage.
01:49Not long after, Caitlyn publicly came out as transgender, marking a transformative chapter in both of their lives.
01:54The secrets of my life, which dishes on their nearly 24-year marriage.
01:59Their splits may have ended one of TV's most-watched love stories, but it also marked the start of a personal reinvention.
02:05What's your relationship like with Kris and the girls and everything now?
02:09What's your relationship like now?
02:10Well, Kris I really never talk to anymore.
02:13Oh.
02:13Yeah, I know it's sad.
02:14Michael Douglas and Deandra Luca
02:16Michael Douglas and Deandra Douglas' ex-wife split up 10 years ago in what was one of the most expensive Hollywood divorces of all time.
02:24In 1977, a 30-some-year-old Michael Douglas married 19-year-old Deandra Luca, the daughter of an Austrian diplomat he met at a White House event.
02:32They quickly became a Hollywood power couple, balancing red carpets and raising their son Cameron, while splitting time between California and a lavish estate in Mallorca.
02:40For more than two decades, the marriage seemed steady, until it wasn't.
02:43In 1995, the couple separated, with the divorce being finalized in 2000.
02:47The proceedings became one of Hollywood's priciest breakups, with her receiving an estimated $45 million settlement.
02:52Deandra is back, claiming under their divorce deal, she's owed half of what he'll earn from the brand new movie.
03:01He got an Academy Award 22 years ago, and she ought to get an Academy Award for chutzpah.
03:06Douglas soon moved on with Catherine Zeta-Jones, whom he married on November 18th, 2000.
03:10And they said it never last.
03:13Arnold Schwarzenegger and Maria Shriver
03:15When action megastar Arnold Schwarzenegger married journalist and Kennedy family member Maria Shriver in 1986, they seemed like the perfect blend of brawn and brains.
03:23Over 25 years, they built a family of four children, navigated his blockbuster career, and even his turn as California's governor.
03:29But in 2011, their marriage imploded when it was revealed that Arnold had fathered a child with a long-time household employee years earlier.
03:36He was born about a week after Christopher Schwarzenegger, Schwarzenegger's youngest child with Maria Shriver.
03:43And that means that both the housekeeper, Patti Bainer, and Maria Shriver were pregnant at the same time in that Brentwood mansion.
03:51Shriver moved out immediately, and though their separation was swift, their legal divorce dragged on until 2021.
03:57Their 25-year marriage had survived fame, politics, and scrutiny, but not betrayal.
04:01I was just, I think, too scared about losing everything, losing her, losing the family.
04:07Reba McIntyre and Narval Blackstock
04:09Country icon Reba McIntyre and her manager, Narval Blackstock, married in 1989, forming both a personal and professional partnership that lasted well over two decades.
04:18I love him and I trust him very much.
04:20Narval helped steer Reba's career as she became one of the biggest stars in country music, and together they shared a son.
04:26For 26 years, they seemed inseparable.
04:28But in 2015, fans were stunned when the couple announced their divorce.
04:31McIntyre announced the couple's decision to split in August, after 26 years of marriage.
04:36Reba later shared that the pair will remain friends.
04:39The two released a joint statement then, saying despite this being the end of their marriage, they continue to support each other.
04:45Their split not only ended a marriage, but also dissolved a professional empire that they'd built together.
04:49And after 26 years, Reba was left to start over on her own terms.
04:53Morgan Freeman and Myrna Colley Lee
04:55Acting great Morgan Freeman and Myrna Colley Lee were married for a whopping 26 years, making theirs one of Hollywood's longest unions before it came to an end.
05:03The Oscar-winning actor and the acclaimed theatre costume designer tied the knot in June 1984, years before Freeman's breakout role in Driving Miss Daisy made him a household name.
05:12What are you doing?
05:13I'm trying to drive you to the stove.
05:15The couple largely stayed out of the spotlight.
05:18They were known for their philanthropy and support of local arts.
05:20But in 2007, the pair quietly separated, and Myrna filed for divorce the following year.
05:25Their marriage was officially dissolved in 2010, bringing to a close over a quarter-century of partnership.
05:30All I want is to be back where things make sense.
05:34Where I won't have to be afraid all the time.
05:36Hugh Jackman and Deborah Lee Finesse
05:38Hugh Jackman and Deborah Lee Finesse met on the set of the Australian series Coralie in 1995, and married the following year, becoming one of Hollywood's most admired couples.
05:47What happened?
05:50Someone I fell.
05:56Did you fall or were you pushed?
05:58Despite a 13-year age gap, they built a solid partnership, adopting two children and staying refreshingly grounded as Jackman's fame skyrocketed.
06:06For years, they were the gold standard of lasting celebrity love.
06:09That's why the world was shocked when, in September 2023, the pair announced their separation after 27 years of marriage.
06:14We have been blessed to share almost three decades together as husband and wife in a wonderful, loving marriage.
06:20Our journey now is shifting, and we have decided to separate to pursue our individual growth.
06:25Their statement emphasized mutual respect and continued family devotion, but fans were heartbroken nonetheless.
06:31Their divorce was finalized in June 2025.
06:33Now, after that statement hit the press, we've seen on Hugh Jackman's Instagram, he's posted a video of himself skipping to the song Bye Bye Bye by NSYNC with the caption, finally.
06:45Whether that is a coincidence or a pointed message, we do not know.
06:49Billy Ray Cyrus and Tish Cyrus.
06:51How are you guys doing?
06:52Because you've had this on again, off again.
06:54We do great.
06:54Oh, man.
06:55We're in the funnest place, man.
06:57We have just reached this place looking at, again.
07:00You're together, not together?
07:01Oh, man.
07:02We're so together.
07:03You are?
07:03Oh, gosh.
07:04We are so together.
07:05Oh, that's good.
07:05Oh, that's awesome.
07:06Yeah.
07:07So together.
07:08Billy Ray and Tish Cyrus tied the knot in December 1993, beginning a country-meets-rock love story that would raise five kids, including Miley, whose fame would later redefine the family.
07:17Over the decades, the pair endured numerous ups and downs, and even filing for divorce twice before reconciling both times.
07:23We both woke up and realized we love each other and decided we want to stay together.
07:28They decided to do something they hadn't done, which was go to couples therapy.
07:32But in 2022, after nearly 28 years together, Tish filed for divorce again, and this time, it's stuck.
07:38Tish, who has filed for divorce from husband Billy Ray, achy, breaky heart Cyrus for the third time.
07:44They finalized the split later that year, closing the chapter on a rather messy note.
07:48Both have since remarried, but their nearly three-decade union remains one of Hollywood's longest and most complicated love stories.
07:55Mel Gibson and Robin Moore.
07:57Now to the divorce settlement between Mel Gibson and his wife of 31 years, Robin Moore.
08:01The nearly $450 million agreement, believed to be the biggest celebrity divorce payout in Hollywood history.
08:09Mel Gibson's marriage to Robin Moore was one of Hollywood's longest and most private unions.
08:13The couple wed in 1980, long before Mel became an international superstar, and raised seven children together.
08:18For years, Robin remained quietly supportive as Mel's fame grew.
08:22But by 2006, their relationship had fractured amid reports of infidelity and substance use.
08:27They separated that year, and their divorce was finalized in 2011, ending a 31-year marriage.
08:33Robin reportedly received millions in one of Hollywood's largest settlements.
08:36But now, the former couple will reportedly split that down the middle, leaving them with each nearly a half billion dollars.
08:43Mel's next relationship with Oksana Grigoriva infamously turned ugly amid abuse claims.
08:48I'm just telling you the truth.
08:50I don't like it.
08:51I don't want that woman.
08:53I don't want you.
08:54He has since carried on a relationship with writer and former equestrian vaulter Rosalind Ross.
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09:15Daryl Dragon and Tony Tennille
09:17Legendary musical duo Daryl Dragon and Tony Tennille, better known as The Captain and Tennille, sang about enduring love with their 1975 hit Love Will Keep Us Together.
09:43The same year, they tied the knot and became one of pop's most iconic couples, performing together for decades.
09:48But behind the music, their relationship was more complicated.
09:51Musically, there was a great synergy, but romantically, it sounded like a nightmare.
09:55Kind of was, because I just was this person constantly looking for something he couldn't give.
10:02And that part was wrong, but the music, we were right there together.
10:06By 2014, after 39 years of marriage, Tennille filed for divorce, later revealing that emotional distance had long defined their partnership.
10:14To me, it should be an intimate, you know, deep, loving connection that happened.
10:20Even with their problems, the marriage lasted 39 years.
10:23Despite the breakup, she remained by Daryl's side as his health declined until his death in 2019.
10:28Their story is proof that even though love may not last forever, compassion often does.
10:32Which long-lasting Hollywood couple do you think will actually go the distance?
10:36Tom Hanks and Rita Wilson?
10:37Denzel and Paul Letta Washington?
10:39Another?
10:39Let us know in the comments down below.
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