The Worst Celebrity Couples in Hollywood

In Hollywood everyone is rich and beautiful but that doesn't necessarily make the best recipe for celebrity dating. We've seen some stellar babes hook up like Ryan Gosling and Eva Mendes and we've seen other couples form the perfect picture of Hollywood bliss like Brad Pitt and Angelina Jolie. Others aren't so lucky and some how hookup with the worst matches they could find in Hollywood. We select a few picks for the worst celebrity couples.

Doug Hutchison and Courtney Stodden

We sure never saw this coming. The "Green Mile" actor made headlines when he married the 16-year-old wannabe country music singer in a 2011 Las Vegas wedding.

If you've seen interviews with the couple you're probably well aware these two seem like bonafide Hollywood wack jobs and Courtney regularly appears to be on some type of substance when she's on camera. We can't actually see this couple lasting much longer but regardless, they're one of the most ridiculous celebrity couples to have ever existed.

Rihanna and Chris Brown

When these two started dating a few years back it seemed like the two were the ideal mix of good looks, talent, and A-list status. Unfortunately that all fell apart when Chris Brown famously assaulted Rihanna after she threw his car keys out the window.

We thought this couple would get the hint they weren't made for each other when Chris was convicted with felony charges and Rihanna was lectured by everyone in the industry about her poor choices in men. These two are recently rumored to be hooking up again and we're so annoyed because they're one of the worst couples in Hollywood history. Is this our generation's Ike and Tina Turner?

Demi Moore and Ashton Kutcher

We feel bad for the recent news surrounding Demi and her health, we really do. However, what were these two thinking when it came to marrying each other? We get that Ashton was super into the idea of hooking up with a Hollywood cougar and Demi probably loved the idea of snagging a young actor after divorcing ex Bruce Willis but we knew the age difference would impact their relationship eventually.

After all, Demi was obviously done having kids and didn't Ashton think he might like to settle down and raise his own family some day? The marriage lasted roughly seven years and honestly, we're surprised they made it that long. Hopefully Demi gets better but this was one celebrity couple headed for disaster as soon as it started.

Jennifer Lopez and Casper Smart

It's sort of funny and sad at the same time when you can see a celebrity going through a mid-life crisis. After JLo dumped her boring husband Marc Anthony last summer we were curious who she was going to date next. A major A-list actor? Another musician in the industry? We thought with Jen's career comeback and newly single status she'd want to pick someone really great.

So when the news broke that she was dating a 24-year-old backup dancer Casper Smart we thought 'Oh nooooooo! Again!? Didn't she learn her lesson with previous backup dancer and ex-hubby Chris Judd?' Apparently not. Hey, look. We're not trying to hate on JLo's man-child of a boyfriend if he makes her happy but we really don't see this lasting.

What celebrity couples do you love to hate?

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