12 celebrity couples who broke up after more than two decades together

The Cyruses, who share five kids including Miley and Noah Cyrus, wed in 1993 while Tish was pregnant with their second biological child, Braison.

The estranged couple have filed for divorce before, in 2010 and 2013, but this time appears to be different. According to court documents, the exes have been separated for two years.

The Jenners' relationship was shown on "Keeping Up with the Kardashians" from the very first episode, though by that point they'd already been married for 16 years and shared two daughters, Kendall and Kylie.

But viewers watched their relationship slowly deteriorate on the show, and the two reality stars announced their separation in 2013, and Kris filed for divorce in 2014. The split was legalized by 2015.

After the divorce, the former Olympic athlete announced that she is a trans woman, and began going by Caitlyn. The process was documented on "I Am Cait" on E!

Anderson, star of "Black-ish," married Stewart in September 1999, almost 23 years ago.

In 2015, Stewart filed for divorce, but they had officially reconciled by 2017. However, in March 2022, People reported that Stewart had filed for divorce for a second time.

The actors met on the set of the 1988 baseball rom-com "Bull Durham." They were together for over two decades and share two kids. Fans were shocked when they announced their breakup in 2009.

"You can't do a meditation on death and stay in a situation that's not authentic," Sarandon told AARP Magazine in February 2014, about how performing in the play "Exit the King" made her question her life. "It made me examine where I was in my union and in my life, and to have discussions about making changes."

The former "SNL" star and recent recipient of a certain slap married Compton a few years after he left the famous sketch show. They have two daughters together.

Fans speculated that there was trouble in paradise after Rock directed, co-wrote, and starred in the comedy "I Think I Love My Wife" in 2007, in which Rock plays a happily married man who is tempted by an old friend coming back into his life, though the couple claimed that their marriage was strong.

However, seven years later in 2014, Rock's wife filed for divorce. Their split was finalized in 2016.

"You get to reset," Rock said of his divorce in 2017. "It's not a breakdown, but something in your life broke down."

These two, for a time, were political and Hollywood royalty, as Schwarzenegger was a huge movie star and the governor of California, while Shriver was his first lady and member of the Kennedy dynasty.

But that came crashing down in 2011 when news of the "Terminator" star's extramarital affair with their housekeeper Patricia Baena and their child together, Joseph, was made public.

Ten years after Shriver filed for divorce, their split was made official in 2021. In total, they had been married for 35 years.

During a Reddit AMA in 2014, Schwarzenegger said, "I'm least proud of the mistakes I made that caused my family pain and split us up."

Lange and Shepard, who died in 2017 due to complications from ALS, began dating in 1982 after meeting on the set of the movie "Frances." They had two kids together, born in 1985 and 1987.

"I mean, we have long periods of relative calm. But then you know," Shepard told The Guardian in 2010. "We're definitely an incredible match. But, you know, not without fireworks … although at this point, you know, she's the only woman I could live with. Who could live with me! What other woman would put up with me?"

The same day that Shepard's death was announced in July 2017, an interview with Lange in AARP Magazine was coincidentally published.

"I wouldn't call Sammy easygoing and funny, but everybody has their dark side, and he always does it with a sense of humor," she said of her ex.

Similarly to other couples on this list, Freeman and Colley-Lee were separated for three years before their divorce was finalized — in this case, they separated in 2007 and were divorced in 2010.

"It was done without a trial," Freeman's lawyer William R. Wright told The Associated Press. "Everybody is glad it's over."

The former vice president and second lady wed in 1970, and they had four kids together: Karenna, Kristin, Sarah, and Albert.

Much was written about their (what some called) excessive PDA on the campaign trail, including this famous kiss at the 2000 Democratic National Convention.

However, their marriage was over just 10 years later. Their split was announced in 2010, after 40 years of marriage. In a statement announcing the breakup, they said it was "a mutual and mutually supportive decision that we have made together following a process of long and careful consideration."

Ford wed screenwriter Mathison, who died in 2015, in 1984, right after his iconic role as Han Solo in "Star Wars" concluded. They had two children together.

In 2000, news broke that they had separated, and Ford had been spotted with actress Lara Flynn Boyle.

By the time their divorce had been finalized in 2004, Ford had begun living with his now-wife Calista Flockhart. Ford and Flockhart are now one of Hollywood's longest-lasting couples themselves.

Stefani and Rossdale met in 1995 when their bands (No Doubt and Bush, respectively) were performing for a local radio station. They dated for six years before getting married in 2002. The rock stars went on to have three sons together.

However, in 2015, news of their divorce broke with Stefani claiming "irreconcilable differences." Over time, it was revealed that the breakup was much messier than it appeared with allegations of infidelity against Rossdale. The divorce was made official in 2016.

"It wasn't until I had to go through the worst tragedy that it really opened up a channel for me to be like, 'God gave me a gift. I'm going to use it now. Because if I don't, I'm going to die,'" Stefani told Time in March 2016, on how her divorce helped her music.

Redford is one of the most famous sex symbols of all time, but in actuality, he was married for the biggest parts of his career. He was just 22 years old when he married Van Wagenen in 1958.

"Obviously, I don't want to denigrate the person I married, there were a lot of good reasons. But I have to say it was to save my life. That's what it felt like at the time," Redford said at Sundance Film Festival in 2018.

Redford and Van Wagenen had four kids together, including one son who died at 2 months old due to sudden infant death syndrome, or SIDS.

In 1985, after almost 30 years of marriage, they split.

"It was mutual and it was right to move on," Redford told The Telegraph in 2001. "We still have great love, great affection, great friendship. It is wonderful, and I think we probably deserve credit for it because the kids are great, they came through it OK."