Photos

 

Can You Believe They Dated?

Oprah and Roger Ebert, Dennis Rodman and Madonna & other odd exes

  •  
    Last week's confirmation of Gwen Stefani and Blake Shelton's totally unexpected relationship has rocked our world to the core -- and inspired us to take a look back at other random relationships in recent Hollywood history. These genre-defying loveships will have your jaw on the floor.

    Pop-punk princess from SoCal meets good ol' boy from Oklahoma. If it weren't for their work together on "The Voice," this would be the most out-of-left-field pairing we could ever humanly fathom.

  •  
    Because he's so committed to keeping his personal life private, we always imagined The Weeknd with an ordinary, non-famous gal... which is why it came as such a surprise when Abel first stepped out hand-in-hand with high profile model girlfriend Bella Hadid back in September.

    Photo: Getty Images

  •  
    When news broke in 2014 that our cute lil baby-faced Nickelodeon alum was dating a "Big" bad rapper, we could hardly believe our ears. Then we listened to their collab, "Best Mistake," and it all made sense. The duo called it quits in April 2015 after eight months together.

    Photo: Getty Images

  •  
    It's not that Taylor Kinney isn't fully deserving of Mother Monster -- we're sure he's a great guy. It's just that we always envisioned Gaga ending up with someone as... eccentric as she is. Taylor just seems so NORMAL! Guess it goes back opposites attract...
  •  
    This three year relationship-turned-engagement was a modern variation of Beauty and the Beast. We can safely assume there was a collective jaw-drop when Evan Rachel Wood and Marilyn Manson confirmed their love back in '07 -- and a subsequent sigh of relief when it was dunzo in 2010.
  •  
    Ordinarily, two rappers dating sounds like a match made in hip-hop heaven. But we always kind of thought hoped Nicki would end up with Drake (#PowerCouple!!!) when she broke up with her ex boyfriend, Safaree Samuels. Also, with all of Meek's beefs, this relationship has been nothing but dramz for Onika!
  •  
    The former JoBro was living life under the radar for the past few years until he burst back onto the scene in September with his new band, DNCE, and mega model galpal, Gigi Hadid. Despite their six-year age difference, and three inch height difference (she's taller), something about this twosome just felt -- off. Joe and Gigi must have felt it too, as they called it quits in early November.
  •  
    Curb Your Enthusiasm star Ted Danson had an affair with Whoopi Goldberg in 1993. Danson was still married to Casey Coates at the time and the affair resulted in one of Hollywood's most epensive divorce settlements costing $30 million.

    Photo: Getty Images

  •  
    Childhood friends, Michael Jackson and Brooke Shields decided to give a relationship a try in the early 1990s. Despite never confirming details of the relationship, Shields gave a tearful speech at Jackson's memorial service.

    Photo: Getty Images

  •  
    Married from 1992 to 1996, the odd-ball couple of Lisa Marie Presley and Michael Jackson met for the first time when Presley was only 7 years old. They got married within 4 months of starting to date and continued dating on and off for the four years following their divorce.

    Photo: Getty Images

  •  
    Seal clearly has a thing for supermodels. Before the "Kiss From A Rose" singer's nin-year marriage to Heidi Klum, Seal dated another Victoria's Secret angel -- Tyra Banks. The couple kept their romance under wraps, only ever showing up to one public event together -- the Essence Awards together in 1996 (pictured above).

    Photo: WireImage

  •  
    Actress Halle Berry had some boy band fever in the late '80s. She and singer Danny Wood of New Kids On The Block became an item in 1989.

    Photo: Getty Images

  •  
    Oprah and Roger Ebert went out on a few dates in 1986. Although the relationship never lasted, we can all thank Roger for encouraging Oprah to syndicate her show!

    Photo: Getty Images

  •  
    Sifting through Chelsea Handler's sarcasm is a Herculean task. The comedienne is well-known for her love of poking fun at pop culture phenomena, people, and events. So when rumors started swirling that the comedienne was dating ultimate gangsta 50 Cent, it felt a little too spoof-able to be true. But nevertheless, the unlikely pair was spotted canoodling at a club in New Orleans in the fall of 2010. Whether Chelsea and Fiddy were ever actually a thing is still a mystery. Either way -- random AF.

    Photo: Getty Images

  •  
    After meeting on the set of the movie Brick, Meagan Good and Joseph Gordon-Levitt briefly dated for about six months during 2005.

    Photo: WireImage

  •  
    Tiger Woods reportedly went out a few times with country star LeeAnn Rimes before she wed Dean Sheremet in 2002. LeeAnn clearly found a way to "live without" him.

    Photo: Getty Images

  •  
    Common and Taraji Henson kept a pretty tight lid on their relationship, but Taraji did admit to Wendy Williams in 2011 that she and Common did, in fact, date!

    Photo: WireImage

  •  
    Minka Kelly and Donald Faison surprisingly dated for about a year before they broke up in 2005.

    Photo: FilmMagic

  •  
    Actors Brad Pitt and Robin Givens met on the set of TV show 'Head of the Class' and began dating in the midst of Robin's divorce from Mike Tyson. The couple dated for around 6 months before they eventually called it quits.

    Photo: Getty Images

  •  
    Back in the summer of 2007, rumors circulated that Shia LaBeouf and Rihanna were dating after the duo was spotted eating together in Beverly Hills. The Transformers star later admitted to going on one date with the "B**** Better Have My Money" singer, but it didn't work out after that. Not everybody can keep up with Bad Gal RiRi.

    Photo: Getty Images

  •  
    In 1988 after speparating from her then-husband make-up artist Ron Snyder-Britton, Kim Basinger dated Prince!

    Photo: Getty Images

  •  
    Rosario Dawson and director Danny Boyle began dating in 2012 after she was cast in his movie Trance. The couple, who was very private about their relationship, went their separate ways in 2013.

    Photo: Getty Images

  •  
    Jermaine Dupri and Janet Jackson split after almost 7 years together in 2009. Apparently the duo couldn't balance work and play and cited Jermaine producing some of Janet's tracks as a point of tension in their relationship.

    Photo: Getty Images

  •  
    Jennifer Lopez and actor Wesley Snipes dated briefly in 1994. They met during filming of the movie Money Train.

    Photo: Getty Images

  •  
    While working on "Diary of a Mad Black Woman" together Shemar Moore and Kimberly Elise were rumored to have been dating. They were spotted getting close multiple times, but their relationship was short-lived.

    Photo: Getty Images

  •  
    Brigitte Nielsen and Flavor Flav, reality TV's craziest celebrity couple met while appearing on VH1's The Surreal Life. The match then starred in their own reality show Strange Love which focused on their relationship and its demise.

    Photo: WireImage

  •  
    It's one of the most iconic couples in hip-hop history -- J-Lo and Diddy. The two icons dated for two and a half years until 2000. Their relationship was at the center of some serious dramz in 1999 after gunfire broke out between Diddy's entourage and another party at a New York nightclub.

    Photo: Getty Images

  •  
    Strange celebrity duo, political pundit Al Sharpton and actress turned fashion designed LisaRaye were paired in 2009.

    Photo: FilmMagic

  •  
    Karrine Steffans, author of Confessions of a Video Vixen, unexpectedly started dating late night host Bill Maher in 2005.

    Photo: WireImage

  •  
    Ray J and Whitney Houston, were spotted getting close in a night club in November 2010 after allegedly breaking off their relationship a year earlier. Houston, who was 17 years older than Ray J, began dating him after her divorce from Bobby Brown.

    Photo: Getty Images

  •  
    Dennis Rodman and Vivica A. Fox were rumored to have briefly dated in 1997. Their relationship was never confirmed but she did take him as her date to the Academy Awards!

    Photo: Getty Images

  •  
    In an unexpected move, Carmen Electra and Dennis Rodman were hitched in a quickie Vegas wedding in 1998. The marriage didn't last very long, and they split after less than a year.

    Photo: Getty Images

  •  
    Madonna had also dated Dennis Rodman in 1994. She wanted to have his baby!

    Photo: Splash News

  •  
    Ray J has a thing for the name Kim. He and rapper Lil Kim were rumored to have been an item in 2007, after they showed up to a party together holding hands.

    Photo: Getty Images

  •  
    Pre-Jay Z, Beyoncé and Mos Def were rumored to be an item in the early 2000s. We don't have anything against Mos Def, but how can you argue a couple whose names rhyme? #JayBey

    Photo: FilmMagic

  •  
    In early 2007, Sienna Miller and P Diddy were spotted looking cozy in Park City. This sparked rumors that the pair were dating. They were photographed a few more times afterwards but were never confirmed as a couple.

    Photo: WireImage

 
 

1070 WDIA is an iHeartRadio Station

© 2016 iHeartMedia, Inc.

*