Celebrity divorces are pretty common, but some shock us all the same — especially when a couple has spent decades together before announcing their split. From ultra-famous flames to romances that fly a bit more under the radar, you can’t help but feel a bit sad in any case of a relationship meeting its end.
While some couples separated amicably and others certainly did not, celebrities who have broken up after decades together have experienced all the ups and downs of love under the scrutiny of the public eye. Cute moments over the years from certain couples made us sure they were built to last, like Dan Akroyd and Donna Dixon working together on movie sets or Reba McEntire and Narvel Blackstock (yes, Kelly Clarkson’s ex’s father) raising a blended family together, and it was a bitter pill to swallow when those couples said their goodbyes. In other cases, these super-long relationships have resulted in extramarital affairs (we’re looking at you, Arnold Schwarzenegger) or multiple divorce filings (like with Tish and Billy Ray Cyrus), and those are a little easier to stomach when the couples decide to separate — we don’t think anyone should go through unnecessary pain, but not all relationships are built to last.
Regardless, it can be hard not to question everything you know when a couple that seemed rock-solid is suddenly on the outs, and we were definitely taken aback by Sylvester Stallone and Jennifer Flavin going their separate ways after 25 years of marriage. Whatever the reasons were for their demise, here are Hollywood’s longest-lasting relationships that resulted in a breakup or divorce after spending over 20 years together.