25+ Celebrities Who Have Walked Down the Aisle Multiple Times

Finding love is hard enough, but imagine how much more difficult it must be to find "the one" when you're famous! From prenups to bitter custody battles, some celebs will keep trying until they strike gold...

Pamela Anderson

Our Baywatch Queen has had her fair share of relationships - 5 marriages, to be specific. We might think it's easy for her to find the man of her dreams, but it was the opposite. Sadly, the bombshell has had her heart broken many times.

In 1995, Anderson and Motley Crue drummer Tommy Lee (above) fell madly in love and got hitched in 96 hours. Despite splitting 3 years later, being with Lee was, "the only time I was ever truly in love," she recalled. Eventually, she moved on to marry Kid Rock in 2006, Rick Salomon in 2014, Jon Peters in secret, and more recently, bodyguard Dan Hayhurst.

Jennifer Lopez

Miss Jenny from the block first married Ojani Noa, who was a waiter in Miami and swept her off her feet in 1997. After a year, they called it quits which took Lopez on to her next marriage with Cris Judd for 2 years. She then hitched singer Marc Anthony in 2004. But, one love triangle had everyones' head spinning...

The early 2000s were tricky. Before meeting ex-fiance Alex Rodriguez in 2005, while she was still married to Anthony, she dated Ben Affleck (above). When Today reported they split after realizing they were "better as friends," before we knew it, Lopez surprised us with the best cultural reset yet and wedded husband #4 - Affleck - in July 2022.

Kim Kardashian

Kim Kardashian's high-profile relationships have been dominating headlines for decades. From her rappers to NFL stars and marriages that lasted mere months, her dating history is one for the books. While Kimmy hasn't kept it a secret she's a sucker for love, there was one guy who ultimately won over the Skims CEO.

First, it was Damon Thomas, whom she married at 19. Then, there was Kris Humphries and the 72-day wedding. Despite splitting from her 3rd husband, Kanye West (above), in 2022, their saga is far from over. "I will love her for life... I will protect her," he said. "I may be divorced on paper, but I'm not divorced of the idea of being the protector." 

Demi Moore

If you know Demi, you know she's a lover of love! Sadly, she had to go through 3 failed marriages in the public eye. Before becoming smitten with Ashton Kutcher and Bruce Willis (below), she learned about marriage with her first husband, Freddy Moore. (*Hence her last name, which she took from him.*)

Demi married American musician Freddy Moore from 1980 until 1985. In her recently released memoir Inside Out, she bravely admitted to being unfaithful to her first true love. She revealed the night before their wedding, instead of working on her vows, she snuck out to see a man she met on a movie set. Well, that's one way to break the news.

Marilyn Monroe

What can you do about young love? Marylin Monroe kicked off the marriage wagon a tad early at 16 years old. In 1942, she married James Doughtery, who was 21 - and her neighbor. About a decade later, Yankees star Joe DiMaggio (below) became husband #2 - but in the end, playwright Arthur Miller was her 3rd and final marriage.

As the face of Hollywood's Golden era, she was a desired bachelorette. While she and Miller never had kids, he stole her heart. "I love him - and he is the only person - human being I have ever known that I could love... as much as myself," she admitted. Despite all this, rumors later emerged over affairs with President JFK and his brother, Robert.

Nicolas Cage

The in-demand actor has truly played the field - from Patricia Arquette to Lisa Marie Presley, Alice Kim (below), Erike Koike, and his recent surprise wedding with girlfriend Riko Shibata. While his 5th marriage has been going seemingly well, welcoming a child together, his previous hitches have lasted about five years, except for one.

Cage and Koike exchanged 'I do''s in Vegas; however, they surpassed Kim Kardashian and Kris Humphries' record. Koike was a 4-day bride. Cage told The New York Times Magazine, "There was a recent breakup. I don't really want to talk about it. I was pretty upset about that and the way things happened." They divorced after 2 months.

Frank Sinatra

He had the voice, the blue eyes, the fame, and the charm. Soul singer Frank Sinatra had his fair share of marriages - 4 to be precise. From childhood sweethearts to fellow Hollywood bombshells and models, he has been married to Nancy Barbato, Ava Gardner, Mia Farrow, and Barbara Marx. He had been bitten by the love bug - hard.

He thought Nancy Barbato was his forever, but his eyes quickly turned to Ava Gardner (above). The same year Sinatra and Barbato divorced, he married Gardner - though he had sparked the romance beforehand regardless. However, according to Ava Gardner: A Life in Movies, the couple reportedly had multiple affairs before divorcing in 1957.

Ava Gardner

This brings us to Ava Gardner. The Hollywood actress did not play the romance card safely. As mentioned, she welcomed a tricky marriage with Sinatra, but had previously been hitched to American clarinetist Artie Shaw and American actor Mickey Rooney (below). For Gardner, she was living a farmer's daughter's dream.

After tying the knot 3 times, she moved to London upon leaving Sinatra. It was time for a fresh start and maybe some British romance. She knew how to stay in control of her destiny and told the Daily Express, "One good man I could love and marry and cook for and make a home for, who would stick around for the rest of my life."

Lisa Marie Presley

The daughter of the King, Lisa Marie, was highly fond of love and secured every chance she could get. Miss Marie tied the knot 4 times throughout her lifetime - from marrying musician Danny Keough in 1988 to Nicolas Cage in 2002 and Michael Lockwood in 2006 - her longest marriage - she had one frightfully regretful experience.

Days after her first divorce, she married Michael Jackson (above). It was the perfect royal match in Hollywood heaven. But fairytales don't always end happily. She wrote via Oprah.com, "The hardest decision I have ever had to make, which was to walk away… I spent a few years obsessing about him and what I could have done different, in regret."

Zsa Zsa Gabor

Socialite and actress Zsa Zsa Gabor walked down the aisle 9 times. While she lived a long and glamorous life, her relationships flourished. Her first marriage was in 1937 to a Turkish diplomat, Conrad Hilton in 1942, George Sanders in 1949, a Dominican diplomat, and the list goes on. And then, of course, there was Richard Brown (below).

But perhaps her most glamorous marriage was to Conrad Hilton. They didn't sleep in the same bed - as Hilton focused on his hotels and religion, and Gabor had lots to say. In a Hollywood biography by Sam Staggs, she joked, "I'm a great housekeeper... Every time I get a divorce, I keep the house."

Billy Bob Thornton

The Love Actually actor has had 6 marriages! His first wife was Melissa Lee Gatlin in 1978, Toni Lawrence in 1986, Cynda Williams in 1990, Pietra Thornton in 1993, and Angelina Jolie (below) in 2000. He is currently married to Connie Angland after dating for 12 years. And he plans to lay low with his dating life.

On Oprah's Mater Class, the actor revealed his issues with fame, referring to his spotlight marriage to Jolie, ending in 2002. He said, "Particularly like when you're in a celebrity marriage… I found celebrity to be difficult just because of privacy issues… I just don't fit in that world at all and get really uncomfortable around it."

Tom Cruise

The Top Gun actor has, too, been married several times: Mimi Rogers from 1987 to 1990, Nicole Kidman in 1990, and of course, the sweetest Hollywood heart in town, Katie Holmes in 2006 (below). However, fans have spotted a particular pattern throughout Cruise's 3 marriages.

MensXP alleged Cruise cuts off his ladies when they turn 33. Although consistent, we don't think this is the real reason for his divorces. Still, we have to credit Cruise for proving his love to all 3 ladies, while having children with two of them! How can we forget when he jumped on the couch on Oprah to declare his love for Katie?

Larry King

The savvy TV host is quite the charmer! Larry King has married 8 times - but to 7 women. It began with his high school sweetheart. Then, he wed two women in 1961, Mickey Sutphin in 1964, Sharon Lepore in 1976, Julie Alexander in 1989, and Shawn Southwick (below) in 1997. So, which leading lady truly stole the King's heart?

King confessed to CNN, "I think in my life I have loved 3 people - married all 3." He told People in 2020, "In my head, I'm not a marrying guy… If you fell in love, you got married." Despite divorcing his high school sweetheart, he married Alene Akins twice, who suddenly died in 2020. King recalled on Twitter, "She was a grand lady."

Richard Pryor

This is no joke. Comedian Richard Pryor made it to the altar 7 times throughout his life - including marrying and re-marrying a few exes. He married Patricia Price in 1961, Deborah McGuire in 1977 (below), Jennifer Lee in 1981, Flynn belain in 1986 and again in 1990 - and then went full circle back to Lee! How did he manage this?

Aside from multiple re-marriages, he was also guilty of adultery. He had a chaotic love life, but he had his unconventional childhood to blame. Growing up surrounded by unhealthy relationships and neglect, he didn't see love the way it should be. He admitted to People in 1978, "I love strong, smart women, but I feel inadequate to them."

Caitlyn Jenner

Jenner's love life has been far from low-key. The gold medal-winning decathlete wed Chrystie Scott, Linda Thompson (below), and of course, momager Kris Jenner. As her time on the track gained momentum, so did her love life. After nearly a decade, she was onto wife #2. She had 2 children with Chrystie, and later, 2 more with Thompson.

Still, her love story with wife #3 - Kris Jenner - takes the cake. 1 blind date and 5 months later, they were married - for 20+ years! "The implication is that I have sold myself out, willingly destroyed what positive reputation I have left," Jenner recalled of their relationship drama. After finalizing their divorce in 2014, the 2 have feuded lots.

Gene Wilder

Gene Wilder lived his wonder years not only as Willy Wonka but as a proud husband - 4 times. According to the Daily Telegraph, he had "marital breakdowns" when his sick mother "left him feeling guilty about being happy." Nonetheless, he wed Mary Mercier in 1960, Mary Joan Schutz in 1967, Gilda Radner (below) in 1984, and Karen Boyer in 1991.

But it was his love story with Radner that ultimately made headlines. Wilder recalled her saying, “I knew I was going to fall in love with you and leave my husband,” upon meeting on the set of a Sidney Poitier film. Sure enough, the two fell madly in love. And when Radner fell ill, Wilder remained by her side until her passing.

Lana Turner

The classic Hollywood actress had 8 marriages, 7 husbands, and 1 daughter. In 1939, she eloped with Artie Shaw. Unfortunately, this short and sweet moment lasted 4 months. On to the next, she married Joseph Crane in 1942, Henry J. Topping in 1948 (below), Fred May in 1960, Robert Eaton in 1965, and Ronald Dante in 1969.

Turner and Crane tied the knot in Vegas. When Turner realized Crane's previous divorce was not finalized, it was donezo! Though Turner had multiple marriages, she was never a part of triangles. When Turner fell pregnant, they remarried - but history repeated itself, and she divorced again after a year. At least they gave it another try.

Brigitte Bardot

The former French star, known as B.B., has said yes to 4 very lucky men. She was the ultimate sex symbol throughout the 50s and 60s and an "international icon," noted Hollywood Life. She married Roger Vadim in 1952, Jacques Charrier in 1959, Gunter Sachs in 1966, and is still married to Bernad d'Ormale, whom she wedded in 1992.

Following flings with industry professionals, a politician captured her heart. D'Ormale told People, "Two weeks after we met, Brigitte phoned Nicolas [her son] because she wanted him to meet me. Just before we left (Norway), she said, 'Why don't we get married while we are there?' So we did. But quietly. I am not a man for the limelight."

Hugh Hefner

Hefner's love life has been the subject of his entire career and bad bunny empire. The Playboy founder first married Millie Williams in 1949, but then once he hit the mansion, he married 2 playmates; Kimberly Conrad in 1989 and Crystal Hefner (below) in 2012. While he dated a few playmates during his career, 2 were chosen to exchange vows.

However, his 3 marriages turned out to be the opposite of a fairytale in the Holmby Hills mansion. Following Hefner's death, his 3rd wife, Crystal, spoke out in the A&E docuseries, "It was toward the end when I started saying no to things that weren't me." From plastic surgery pressure to feeling trapped, she held on to secrets for years.

Britney Spears

Britney hasn't just made headlines for her career and conservatorship. Today, she's married to her 3rd hubby, Sam Asghari (below), whom she met on the set of her 2016 music video for Slumber Party. "I was excited that I'd get to meet one of the biggest artists of all time," the personal trainer recalled. "I had butterflies."

Spears was previously hitched to Kevin Federline, with whom she shares her children, Sean Preston and Jayden James. Others lasted a bit shorter: In 2004, the Toxic singer flew her close pal, Jason Alexander, to Vegas. She thought, why not give things a go? The two eloped on New Year's, but the marriage lasted a total of 55 hours. 

Dennis Rodman

The former American basketball player has shot his shot multiple times to see if anyone would fit the wifey role. Rodman has been married 3 times: Annie Bakes in 1992, Carmen Electra in 1998, and Michelle Moyer from 2003 until 2012. While he never believed in monogamy at first, all it took was some powers of persuasion.

In Rodman's memoir, he speaks about how his daughter convinced him to marry. He wrote, "Alexis was the one who talked me into it. She was 3 years old at the time… My little girl kept saying, "ARE YOU GONNA GET MARRIED?... and finally, I buckled." Sure enough, in 1996, he famously "married" himself, clad in a wedding dress (above)!

Elon Musk

The Tesla CEO has more on his mind than robots and Mars. It's a busy life being one of the wealthiest humans on the planet. So, why not splash the cash on a few weddings? Musk has been divorced 3 times, dated multiple celebrities, and has 10 children. He married Justine Musk in 2000 and Talulah Riley (below) in 2010 - and again in 2013.

Elon and Talulah had an agreement when it came to labels. Riley told The Independent, "I suppose the reason to get remarried was just that it felt silly to be unmarried together after being married… We were saying, 'This is my husband.' 'This is my wife.' 'Oh, wait, no, we're not that anymore. We better be that again." Because why not?

Charlie Sheen

How could we single-handedly skip one of television's most iconic playboys? Two & A Half Men's Charlie Sheen was known for being completely against monogamy on the show - but in real life, there were only 3 women who sealed the deal with a ring. He married Donna Peele in 1995, Denise Richards in 2002, and Brooke Mueller in 2008.

After a match-up on set, Denise Richards knew he was "the one" after their 2nd date, per People. Who would have thought that a bombshell like Richards would have to play it cool? They had their ups and downs, from having children to divorces and Twitter feuds, custody battles, and lawsuits; We guess they just weren't meant to be...

Paul McCartney

For the Beatles' charmer, it was a hello, goodbye 3 times! He married Linda McCartney in 1969 (below), Heather Hills in 2002, and Nancy Shevell, who remains his wife today! While he is a happily devoted man today, McCartney had his fun back in the day - especially being in one of the most popular bands in the world.

Being young and in love is full of surprises. According to Nights With Alice Cooper, McCartney recalled the night before he and Linda tied the knot, "I'm not sure that there is a perfect marriage, but yeah, we did have a row, strangely enough. And it was like, 'Oh, forget it! Let's go get married.'" If only all decisions were this easy.

Madonna

Our pop disco girl Madonna has only been married twice in her life, excluding her wild dating scene. She married American actor Sean Penn in 1985 and Guy Ritchie in 2000. They say love never fades away, and Madonna will always remember the first man who she said "yes" to. According to People, she still may have those feelings.

Penn (above) and Madonna were married from 1985 until 1989. The 4-year marriage had its highs and lows, but things started to heat up when previous domestic violence accusations came into play. While these reports came out in 1987, Madonna remained to back her ex-husband and revealed at a charity gala in 2016 that she was "still in love."

Jennifer Aniston

The 'it' girl of the 90s was married twice - first, to Justin Theroux from 2015 until 2017. But we all know the real reason why you're all here: Jennifer Aniston and Brad Pitt (below) were the couple that people still talk about today - despite divorcing in 2005 after a 5-year marriage. We couldn't pair a better-looking couple if we tried.

They began dating in 1998 while Aniston was formerly known as Rachel on Friends, and Pitt even guest starred on the show! The two parted ways, but Aniston revealed to Vanity Fair, "I will love [Brad] for the rest of my life. He's a fantastic man. I don't regret any of it, and I'm not going to beat myself up about it."

Johnny Depp

While the Willy Wonka actor was married to Lori Anne Allison from 1983 until 1985, it's his relationship with wife #2 Amber Heard (below) that he will never forget - and neither will the world! Depp fell for Heard after meeting on the set of their 2009 film, The Rum Diary. Sadly, their romance took a brutal turn.

In 2016, Heard filed for divorce, citing assault allegations. But later in 2022, a defamation trial against the actress kicked off. "I tried the best I could to make a deeply broken relationship work, and I couldn't," she recalled of their toxic relationship. Sure enough, she was ordered to pay roughly $1 million to her ex.

Heidi Klum

Our Halloween Queen, Heidi Klum, has been married 3 times in her life… so far! In 1997, she married Ric Pipino, Brit Singer Seal (below), in 2005, and is currently married to guitarist Tom Kaulitz. However, Klum set an example for those celebrities, making sure us regular folk know it's not so easy to find love and get hitched!

According to People, Klum and Seal renewed their vows 8 times to try and make things work. The supermodel said they would say 'I do' on their anniversary, "I thought it would be kind of, like, fun. I thought it would be a fest of love," Klum continued. "But you know, that doesn't work either. I tried, you can't say I didn't try!"

Alec Baldwin

From American actresses to yoga instructors, Baldwin is a man of many lovers. His first wife was Kim Basinger from 1993 until 2002 - and a decade later, he met his forever wife, Hilaria, in 2012! While Baldwin is happily married to his second wife Hilaria (below), with 7 kids together, his first relationship ended differently.

According to the Daily Mail, Basinger and Baldwin met on the set of a romantic comedy in 1991 and were married 2 years later. Unfortunately, they split and underwent a "bitter custody battle" over their daughter. All things aside, she confirmed, "We're all fine, and we all get along, whatever. But he's been — but he's a challenge."

Liza Minnelli

Our Cabaret star Liza Minnelli has been hitched 4 times in her life. She first said 'I do' to Peter Allen in 1967 (below), which ended in 1974. She then moved on to Jack Haley Jr. in 1974, married Mark Gero in 1979, and, more recently, wed David Gest from 2002 to 2007. Though all is fair in love and war, Liza encountered more war.

Minnelli's marriage to David Gest was far from loved-up. They were only married for 16 months, and Liza was truly smitten at first, while Gest thought she was the most beautiful woman in the world, per NBC News. In 2004, he said, "don't go near her," after filing for divorce and suing his ex-wife for $10 million over domestic violence.