8 celebrity couples who split up after more than two decades: Caitlyn and Kris Jenner’s 24-year marriage, Gwen Stefani and Gavin Rossdale’s messy divorce, and Miley Cyrus’ parents Billy and Tish ....

May 16 , 2022

Gavin Rossdale and Gwen Stefani, Kris Jenner and Caitlyn Jenner, Tish Cyrus and Billy Ray Cyrus … Showbiz isn’t always glamorous, especially in the case of divorce. Photos: AP; Wire Image; Getty Images

Chris Rock, the victim of Will Smith’s slap, was married to Malaak Compton for 20 years – as was Star Wars OG Harrison Ford and Melissa Mathison

Maria Shriver found out hubby Arnold Schwarzenegger had a love child with their nanny, Sam Shepard and Jessica Lange had a long run, and what about Morgan Freeman?

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

Tish Cyrus and Billy Ray Cyrus, parents of US actress and singer Miley Cyrus, arriving for the premiere of The Last Song in Hollywood, California, USA in 2010. Photo: EPA

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

Caitlyn and Kris Jenner had a very public relationship thanks to the show, Keeping Up with the Kardashians. Photo: @lahlahbean/Twitter

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

Megalyn Echikunwoke and Chris Rock were together for four years after his divorce from Malaak Compton-Rock. Photo: Getty Images/Vogue