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.

  • 1
    10,408 VOTES

    Courtney Stodden And Doug Hutchison

    Doug Hutchison wasn’t much of a celebrity until he married a 16-year-old virgin. The character actor met Courtney Stodden, 35 years his junior, online. After a bit of courtship, their parents gave the actor consent to marry their daughter. Stodden and Hutchison wed in 2011. They split up in 2013 due to their age gap, but it didn’t last long. They got engaged in 2014, with Stodden saying that they had given other men a try and missed their husband. Their divorce was finalized in 2020.

    Besides the age thing, it was Stodden’s behavior during an ABC interview that went viral. Stodden’s dad is four years younger than Hutchison.

  • 2
    11,353 VOTES

    Mary-Kate Olsen And Olivier Sarkozy

    When former Full House darling Mary-Kate Olsen was seen cozying up to the brother of the former president of France, people balked. The two seemingly come from different worlds and the 17-year age difference made this odd celebrity couple even stranger.

    The French banker and the actress-turned-fashion designer married in 2015 and divorced in 2021.

  • 3
    10,553 VOTES

    Jennifer Aniston And Adam Duritz

    This odd couple is even odder now. Jennifer Aniston was a hot star in 1995, thanks to Friends, and Counting Crows was a big-time band. Adam Duritz dated Aniston’s Friends costar and bestie Courteney Cox right after.

    Duritz defended this move by saying, “[Aniston and I] never even slept together.”

  • 4
    9,357 VOTES

    Courteney Cox And Adam Duritz

    The news of their relationship was met with a lot of head scratching back in 1997. The Friends star appeared in the Counting Crows video for “A Long December,” causing music fans and TV fans to consider a whole new dating pool.

    Considering Adam Duritz also dated Jennifer Aniston and Emmy Rossum, it’s strange to know that he would end up on Tinder in 2014, having not yet found "the one."