What’s sadder than a break-up? A break-up after multiple decades together! Did you know all these celeb couples sadly through the towel in after more than two decades together? 1. Billy Ray Cyrus and Tish Cyrus filed for divorce after 28 years of marriage in April 2022 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, and Tish filed for divorce once more in April. 2. Kris Jenner and Caitlyn Jenner were officially divorced in 2015 after 24 years of marriage 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 legalised 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! 3. Chris Rock was married to Malaak Compton-Rock for 20 years, from 1996 to 2016 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. The Met Gala 2022’s best and worst dressed stars, from Kim K to SJP However, seven years later in 2014, Rock filed for divorce. Their split was finalised 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.” 4. Maria Shriver and Arnold Schwarzenegger filed for divorce in 2011 after 25 years of marriage 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 Mildred 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.” 5. Sam Shepard and Jessica Lange dated for almost 30 years before confirming their split in 2011 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 1986. “I mean, we have long periods of relative calm,” 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?” Will Barron Trump go to prom? Here’s how 5 other first children did it 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 easy-going and funny, but everybody has their dark side, and he always does it with a sense of humour,” she said of her ex. 6. Morgan Freeman and Myrna Colley-Lee were married for 26 years before their split in 2010 Similarly to other couples on this list, Freeman and Colley-Lee were separated for three years before their divorce was finalised – 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.” 7. Harrison Ford has been married three times – his longest marriage being 20 years with Melissa Mathison Ford wed screenwriter Mathison, who died in 2015, in 1983, 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 finalised in 2004, Ford had already met his now-wife Calista Flockhart in 2002, and married in 2010. Ford and Flockhart are now one of Hollywood’s longest-lasting couples themselves with over 20 years together – 12 of them married. 6 stars shunned by the Kardashians, from Blac Chyna to Larsa Pippen 8. Gwen Stefani and Gavin Rossdale were together for 20 years Stefani and Rossdale met in 1995 when their bands (No Doubt and Bush, respectively) were performing for a local radio station. They dated for over 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 break-up 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. This article originally appeared on Insider Want more stories like this? Follow STYLE on Facebook , Instagram , YouTube and Twitter .