The Oddest Celebrity Couples In Recent Memory

List Rules
Only couples that were together in 1990 or later. Couples do not have to currently be an item.

When you’re a celebrity, the dating pool gets pretty small pretty quickly because celebrities sometimes find it difficult to date mere mortals. When your profile is high, one does not simply swipe right and hope for the best, unless you are Adam Duritz. Because the industry is closed off, young actors make some rash mistakes, or the beer goggles were on during that yacht party, and the world ends up with some odd celebrity couples.

There’s chemistry and then there’s weird science chemistry. There’s also publicity. One up-and-coming star may hitch their wagon to a popular shiny one. Sometimes both weird celebrity wagons hit the curb and roll off a cliff, selling clicks and magazines across the nation. Strange celebrity couples always make the headlines. Remember that time Moby said he dated Natalie Portman? Or when Rosario Dawson dated Danny Boyle?

There are youthful mistakes such as Drew Barrymore and Tom Green. But then there are the supernova weird Hollywood couples such as Edward Norton and Courtney Love or Billy Corgan and Tila Tequila. We may not know why these famous couples got together, but we do know that Duritz and David Spade were getting all the hottest ladies at one point in time. Like we said, that dating pool can get small and crowded. No wonder it’s stocked with the oddest celebrity couples.

Who’s your favorite strange celebrity couple? Are you new-school or old-school? Or does weird not pay attention to eras? Upvote the oddest of the odd celebrity couples and be thankful your own relationships aren't on display.