Celebrities Who Have Been Married At Least Five Times

For some people, getting married is a once-in-a-lifetime milestone. For others, it's something they're willing to try again if the first time doesn't work out. In Hollywood, finding lasting love can be especially complicated, but while plenty of famous marriages stand the test of time, others come to an end just as quickly as they began. And then there are the stars who never let a divorce stop them from giving love another shot. There's no shortage of stars who have said "I do" two or three times, but there are a few stars who have been married four times — or more. Some eventually found lasting happiness, while others continued searching for that once-in-a-lifetime love. Of course, having multiple marriages doesn't necessarily mean someone is unlucky in love. Many celebrities have spoken openly about how each relationship taught them something new about themselves, even if it ultimately ended in divorce.

Over the years, some of these celebrities got married after breaking up, while others found themselves with an entirely new partner each time they walked down the aisle. No two stories are exactly alike, but they all have one thing in common: a willingness to keep believing in love despite heartbreak. One of the celebs that falls into that category is Pamela Anderson, who has been married five times — and isn't opposed to getting married again. Or even actor Gary Oldman, who's on his fifth marriage. Let's dive in.

When most people think of Billy Bob Thornton's love life, they think of his relationship with Angelina Jolie. But while that may have been the "Landman" star's most public romance, he's actually been married four other times. In fact, his first marriage was decades earlier. Back in 1978, Thornton married Melissa Lee Gatlin, but the two divorced in 1980 after welcoming their daughter, Amanda Brumfield. In 1986, Thornton tied the knot again, this time with Toni Lawrence, but that marriage only lasted two years. In 1990, the actor married Cynda Williams, but they divorced in 1992. A year later, Thornton married Pietra Dawn Cherniak, and they had two sons together before going their separate ways in 1997. 

In May 2000, Thornton and Jolie eloped in Las Vegas after a whirlwind two months together. Their red-hot romance — that included getting tattoos for each other — fizzled out, and they divorced in 2003. That same year, Thornton met Connie Angland, who was working as a special effects artist on his film, "Bad Santa." The two started dating and even had a child together, but he was hesitant to remarry. "I told Connie I didn't want to put her through that. We've been together for four years now. We have a child together," he told Maxim in 2008."If we get married, then the press will start calling her 'Number Six.'" More than a decade into their relationship, Thornton softened to the idea of getting married. In an interview on "The Late Late Show With James Corden," Thornton said that he and Angland ultimately tied the knot for their daughter. 

In 1995, Pamela Anderson found love with Mötley Crüe drummer Tommy Lee. The two met on New Year's Eve at the Sanctuary club in Hollywood and they went on their first date two months later. After talking for a couple weeks, Lee and Anderson agreed to meet up, but she was set to fly to Cancun for a photoshoot. And so, he did what any other guy would do. He booked a flight and headed to Mexico. "The first thing he said to me was 'I'm going to marry you,'" Anderson recalled during a 2002 interview with CNN's Larry King. Three days later, Lee proposed and they married the next day. Their marriage didn't last, however. After welcoming two sons, Anderson and Lee separated in 1998.

Anderson's love story didn't end there. She'd go on to meet Kid Rock at a VH1 event in April 2001. The two dated for two years and even got engaged, but they broke up in April 2003. Three years later, they reconnected and tied the knot in July 2006. The then-couple exchanged vows at three separate weddings only to divorce within four months. The "Baywatch" alum went on to marry professional poker player Rick Salomon, whom she divorced after six months and remarried in 2014. Following her second divorce from Salomon, Anderson married movie producer Jon Peters, but they split just 12 days later and said they were never legally married. In 2020, Anderson married her bodyguard Dan Hayhurst, but they went their separate ways after about a year. Believe it or not, the actress isn't opposed to marrying again. During an interview with Jimmy Kimmel, Anderson was asked if she'd ever remarry. "I hope so, I don't know. I still have a lot of life left," she replied.

Dame Joan Collins is another actress who has been married five times. Her first husband was actor Maxwell Reed, whom she met when she was just 17 years old. Four years later, however, the two divorced. The "Dynasty" star went on to wed Anthony Newley (1963 to 1971), Ron Kass (1972 to 1983), and Swedish singer Peter Holm (1985 to 1987) before she met the man who seemingly changed everything.

Percy Gibson was the producer of "Love Letters," a play that starred Collins back in 2000. Despite a considerable age gap — Gibson is three decades younger than Collins — the two became friends. After closing the curtain on "Love Letters," Gibson and Collins started dating and eventually fell in love. The pair tied the knot in London in 2002 and have been together ever since. "I kissed a lot of frogs before I found my prince," she wrote in her 2011 memoir "The World According to Joan," according to People magazine. "For those women who are looking for a life partner, that old saying that men are like buses and 'if you wait long enough the right one will come along' is true for a reason."

Gary Oldman has portrayed some of the most incredible characters on-screen, but his personal life has also been full of memorable chapters. The Oscar-winning actor has been married five times. In 1987, Oldman married his first wife, actress Lesley Manville, with whom he welcomed his son, Alfie. The two split in 1990 — the same year that Oldman married actress Uma Thurman. The two broke up two years later. "We met when I was 18. He was 12 years older. It was a crazy love affair that ended, as it needed to. He was my first love," Thurman told Vanity Fair in 1996. Oldman went on to marry model Donya Fiorentino in 1997, with whom he had two children before their 2001 divorce, and Alexandra Edenborough, who he married in 2008 and divorced in 2015.

He married his fifth wife, writer Gisele Schmidt, in 2017, though it's unclear how the two originally met. According to The Sun, Oldman proposed to Schmidt while he was dressed up as Winston Churchill, and the two exchanged vows at the home of Oldman's manager, Douglas Urbanski. "You know, sometimes you have to go through the others," Oldman told reporters in November 2018, per the outlet. "I've gone through my thing and we're like peas in a pod ... I'm nearly 60 and at last, I think I've come home," he added.

Iconic director Martin Scorsese is best known for films like "Taxi Driver" and "Goodfellas," but the acclaimed filmmaker's personal life has also had its fair share of twists and turns. Scorsese has been married five times throughout his life. He married his first wife, Laraine Marie Brennan, in 1965, but they split in 1972. Four years later, Scorsese married author Julia Cameron, but that relationship didn't last, and the two split in 1977. Scorsese was married to actress Isabella Rossellini from 1979 until 1982 and Barbara De Fina from 1985 to 1991, before finding the love of his life. The Oscar winner first met Helen Morris in 1995 when she was working for Scorsese's pal Michael Powell. The two didn't hit it off right away, but their fondness for one another grew with time. The two exchanged vows in New York City in 1999. "You make a family with a person like Helen," Scorsese told Talk magazine in 2000, according to People. Four months after tying the knot, Morris gave birth to the couple's daughter, Francesca. 

Morris was diagnosed with Parkinson's more than 30 years ago. Despite the progression of the disease, Scorsese has remained by his wife's side. "I've never seen such strength like that in a person and such a fortitude and a positive way of approaching life under the worst of circumstances," Scorsese said on an episode of the SiriusXM podcast, "This Life of Mine with James Corden" in 2024 (via People). Scorsese and Morris will celebrate their 27th wedding anniversary in July 2026.