16 Celebrity Couples You Won't Believe Dated (PHOTOS)

16 Celebrity Couples You Won't Believe Dated (PHOTOS)

Some celeb couples seem to be a no-brainer, like the hotness that is Brangelina -- two people who have humanitarian causes in common as well as good looks. But some unions are a bit out there, whether they were rebound flings or straight-up strange marriages (Jolie and Billy Bob Thornton, anyone?).

Here are 16 weird celebrity couples that made us say, "Huh? What? With whom?" all at once! 


Image via © Chris Polk/FilmMagic for Us Weekly Magazine

  • Angelina Jolie & Billy Bob Thornton


    Image © Reuters/Corbis

    They wore vials of each other's blood on necklaces they wore around their necks. Yup, it was that kind of relationship. Though he was 20 years older than she, they were united in weirdness beyond blood. There was also a mutual love of knives. And PDA. Lots of that. 

  • Mariah Carey & Nick Cannon


    Image © Erik Pendzich/Demotix/Corbis

    It seems like people were laying bets on how long Mariah Carey and Nick Cannon would last as soon as the Couple-No-One-Saw-Coming got married. After all, Mariah Carey is the diva with a flair for drama and he is the uber-chipper host of America's Got Talent. Sure enough, twin babies and mutual tattoos notwithstanding, the pair separated in 2014 after six years of marriage.

  • Michael Jackson & Lisa Marie Presley


    Image ©Mark Cardwell/Reuters/Corbis

    The King of Pop and Elvis' daughter felt the need to kiss in public at the 1994 MTV Video Music Awards simply to prove that they were indeed a couple, however cringeworthy the moment was. Less than two years later, the pair divorced. Presley later told Oprah Winfrey that she felt she could save Jackson, who had recently been accused of child molestation and was in failing health, partly due to a drug addiction. 

  • Katy Perry & Russell Brand


    Image © Danny Moloshok/Reuters/Corbis

    Katy Perry and Russell Brand locked lips in a scene from Get Him to the Greek that was cut from the film. They rekindled their romance at the MTV Video Music Awards and married 10 months later, in 2010. But the former Christian singer and the bad boy comedian didn't last — partly because of the strain her busy touring schedule put on the new marriage. He famously texted her to tell her it was over. 

    More from The Stir: 10 Celebrity Couples Who Loved Each Other So Much, They Got Married Twice! (PHOTOS)

  • Jessica Simpson & John Mayer


    Image ©Jackson Lee/Splash News

    Nine months after splitting from husband Nick Lachey, Jessica Simpson, who once famously expressed confusion over whether canned tuna was in fact chicken, hooked up for 10 months with John Mayer, the brainy musician. Perhaps 'hooked up' is an understatement. Mayer later (tackily) talked to Playboy about being addicted to Simpson sexually, calling her 'crack cocaine' and 'sexual napalm.' 

  • Evan Rachel Wood & Marilyn Manson


    Image © Splash News

    Eyeliner. That's what actress Evan Rachel Wood once said attracted her to shock rocker Marilyn Manson. With a foundation like that, is it really any wonder that the off-and-on relationship (2006-2010) failed? Despite the then up-and-coming starlet's gushing about Manson's smarts and creativity, the pair both later described their relationship in one word: Mistake.

  • Tom Cruise & Cher


    Image © MCaulfield/WireImage

    They could have measure their age difference in decades, if they were interested, but Tom Cruise and Cher were probably too busy getting it on to focus on that. Their brief fling in the '80s, before his marriage to first wife Mimi Rodgers, was a secret until recently, when Cher called Cruise one of her top five lovers of all time. High praise indeed.

  • Justin Timberlake & Fergie


    Image © Chris Polk/FilmMagic for Us Weekly Magazine

    OK, they're both pop stars now, but what did Justin Timberlake and  Fergie have in common when they were in a relationship back before either was a household name? Not sure we want to know. After all, he was 16 and she 23. Eww.

    More from The Stir: 10 Celebrity Couples Who Called Off Their Engagement & Never Made It To the Altar (PHOTOS)


  • Flavor Flav & Brigitte Nielsen


    Image © Anna Pocaro/London Entertainment/Splash News

    Left field doesn't begin to describe the source of the relationship between rap-pioneer-turned-reality-TV-clown Flavor Flav and amazon woman Brigitte Nielsen, former actress and wife of Sylvester Stallone. They met on VH1's The Surreal Life and got their own spinoff show, Strange Love. It lasted about as long as their relationship, which was riddled with jealousy and yelling. 

  • Mary-Kate Olsen & Olivier Sarkozy


    Image © Johns PKi/Splash News

    Never mind that Mary-Kate Olsen still looks like she's 12. There is an actual 17-year difference between her and husband Olivier Sarkozy. That's not the only difference. He was a famous womanizer; she is famously private. But they have at least two things in common: money and status. She was wealthy before hitting adulthood, thanks to kid videos as one-half of the Olsen twin money machine, and he is a banker and brother to former French president Nicholas Sarkozy. At least she knows he's not in it for cash and fame.

  • Sandra Bullock & Jesse James


    Image © Danny Moloshok/Reuters/Corbis

    America's sweetheart apparently wanted to be part of something a bit less wholesome, or so many thought, when she married Jesse James, motorcycle builder and host of Monster Garage. Then he cheated on her and became the most hated man in America while she filed for divorce.

  • Julia Roberts & Lyle Lovett


    Image © Frank Trapper/Sygma/Corbis

    Predictably, the press called them beauty and the beast. Julia Roberts was the glamorous redhead with the big smile who wed the quirky country singer with hair like a bird's nest just three weeks after meeting. But it was another difference that reportedly broke them apart: Their wildly different schedules (Lovett once said he never spent an uninterrupted week with his wife) and her rumored infidelities while away.

    More from The Stir: 21 Female Hollywood Stars Who Married Regular People (PHOTOS)

  • Hayden Panettiere & Wladimir Klitschko


    Image © infgebe-05/INFphoto.com/Corbis

    She's 5'1 and he's 6'6. Now you know how they met and why they fell in love. "I said, 'You're huge' and he said, 'You're tiny," And that was it," Panettiere told Ellen De Generes. Well, not quite. The unlikely duo, she the star of Nashville and he the Ukranian boxer and Olympic champion, dated for two years and broke it off due to their differing schedules. Then they rekindled their love, got pregnant and married.  

  • Madonna & Warren Beatty


    Image © Sunset Boulevard/Corbis

    If you want to know what a singer in her prime (Madonna) would find appealing about a much older man (Warren Beatty), let her say it herself: "He was an incredible lover," the Material Girl told Howard Stern recently. She also liked the challenge. He had slept with "all of Hollywood," she said, including Brigitte Bardot, Elle McPherson, and Julie Christie, and "I have confidence in my skills." Their dalliance lasted 15 months.

  • Tila Tequila & Billy Corgan


    Image © Kiley Bishop/London Ent/Splash News

    Epically eccentric frontman Billy Corgan's dating history is all over the place. The Smashing Pumpkins' frontman has dated Jessica Simpson, who once said he "braids my prayers," Courtney Love, with whom he later had a public feud, and supermodel Helena Christensen. His weirdest connection, though, may have been with MTV's Tila Tequila. The two attended Bravo's A-List Awards in 2009, made a weird home video together, then apparently went their separate ways.

  • Christina Hendricks & Geoffrey Arend


    Image © Lucy Nicholson/Reuters/Corbis

    On the surface, they seem like the second coming of buxom bombshell Marilyn Monroe and nerdy playwright Arthur Miller. But when Mad Men actress Christina Hendricks and theater actor Geoffrey Arend met at a party, she just saw a cute guy with disheveled hair and geeky glasses. Then she married him, period. 

    More from The Stir: 20 Male Hollywood Stars Who Married Regular People (PHOTOS)

celeb couples

More Slideshows