4. Billy Joel
Our favorite piano man, Billy Joel has seen his share of romantic ups and downs, which have made for some great music over the years. But it looked like Joel had finally settled down in his late 50's with the beautiful foodie, Katie Lee Joel. Unfortunately, after only five years (and a big boost to Katie Lee's career), the two split, leaving Joel, 61 and alone. Billy Joel Splits from Katie Lee
5. Val Kilmer
He was one hot caped crusader, so perhaps there's a Batman curse, since Val Kilmer, like some of the other actors who starred in the comic book series (a few of which made our list), including Clooney, Nicholson, and Keaton (not to mention the newly single, Jim Carrey), Val Kilmer is on the verge of 60 and all alone. And judging by the pounds Kilmer recently packed on, it looks like he's been spending more time with a tub of Ben & Jerry's than looking for love. But hey, Val, we get it—there's no better company than a pint of Chunky Munky when you're feeling lonely.
Photo via INF.