If you’re one half of a celebrity super-couple, breaking up must be hell. For a start, you probably can’t open a magazine or click on a webpage without hearing how well or how poorly your former significant other is doing. Plus, you can rest assured that even long after the dust has settled, the tabloids and the public will still remember your celebrity split. And so the world will be observing both you and your famous ex, comparing you, even, and most likely watching to see who has fared the best – and the worst – during your time apart.
20. Charlie Sheen and Denise Richards
Charlie Sheen and Denise Richards were married from 2002 until 2006, and it was a rocky relationship to say the least. The couple had two children together and made some attempts at remaining amicable for their sake, but by 2016 relations had hit a new low. And, of course, by that point, Sheen’s once-good looks had gone. So yeah, it’s fair to say that Richards came off the best out of this one.
19. Cameron Diaz and Justin Timberlake
Cameron Diaz and Justin Timberlake were the pop culture super-couple of the early noughties. They started dating in 2003, and their relationship continued through three years of media scrutiny until it reached what seems to have been a fairly amicable end in 2006. So amicable, in fact, that the couple were able to reunite in 2011 for the movie Bad Teacher with no bad blood. And honestly, we’d have to call it a draw in the battle of the aging ex here, with both stars still looking as hot as ever.