29.2k voters

The Oddest Celebrity Couples In Recent Memory

Updated August 31, 2021 333.7k votes 29.2k voters 2.1m views41 items

List RulesOnly 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.

  • 5

    Evan Rachel Wood And Marilyn Manson

    She was 19. He was 36. “People were pretty mean," Wood told The Daily Beast. "At the time I hadn’t yet been exposed to that kind of cruelty from strangers." The actress later married Jamie Bell and started a family.

    “If people were wondering why I was acting so-called crazy or like a teenager, it’s because I was,” she said. “People go through phases. People make mistakes. People go through life and don’t get it right every time.”

    Is this a weird couple?
  • 6

    Jerry Hall And Rupert Murdoch

    Jerry Hall and Rupert Murdoch got married in 2016. They were 59 and 84, respectively. It's Murdoch's fourth marriage, but it's technically Hall's first, as her marriage to Mick Jagger from 1990 to 1999 was declared void by the British government.

    Hall and Murdoch were first seen together at the 2015 Rugby World Cup Final between Australia and New Zealand. 

    Is this a weird couple?
  • 7

    Roger Ebert And Oprah Winfrey

    Their two dates didn’t turn into a long-term relationship but they did make Oprah the reigning queen of daytime TV and a living legend. Ebert recounted how he advised her on taking a deal with either ABC or King World. On their date at Hamburger Hamlet, Ebert did some simple math and showed Winfrey just how much a syndication deal with King World would make her.

    She made up her mind in 10 seconds: “I’m going with King World.” They may not have waltzed down the aisle, but we do have Ebert to thank, in part, for Oprah.

    Is this a weird couple?
  • Photo: Chelsea Lately / E!

    Chelsea Handler And 50 Cent

    This strange celebrity couple dated in 2010. Handler met the Queens native on her show Chelsea Lately. They immediately connected and flirted, even with her love for vodka and his famed sobriety.

    They continue to flirt on social media, so there seems to be a lot of healthy feelings still lingering.

    Is this a weird couple?