How Did They Even Meet? 15 of Hollywood’s Oddest Couples and Strangest Hookups!

Anything can happen in Hollyweird. For example, celebrities who don’t even walk in the same circles can meet, hookup, and fall in love. The celebrities on this list formed some of Hollywood’s oddest couples and strangest hookups. Check it out!

1. Rihanna and Josh Hartnett

The two met while she was hosting an episode of TRL on which he was the guest in 2007. Rihanna reportedly gushed about him saying, “He is so hot and he is really sweet to me…when we hang out it feels right – even though it’s pretty new. I would be lying if I told you we were not more than just friends… I have so fallen for him, he’s lovely.”

2.Vanilla Ice and Madonna

Vanilla Ice and Madonna dated for 8 months back  in the 90’s, but Ice, whose real name is Robert Van Winkle, broke it off when Madge published her coffee table book SEX which features the two in sexual pictures as well as photos of Madonna with other men. “It was disgusting and cheap,” Vanilla Ice said in an interview, “We were in a relationship yet it looked like she was screwing all these other people.” Though, he also said she was a “great lover.”

3. Melissa George and Russell Simmons

 Photo (L): Rob Rich/, (R):  Lia Toby/

Okay, this is a pair that’s got us wondering “how did you two even meet?” The hip-hop mogul and the Australian actress were spotted kissing in July 2011. They dated until Feb. 2012 when they called it quits due to the strains of a long distance relationship.  Melissa George has remarked that their relationship was “absolutely lovely.”

4. Britney Spears and Colin Farrell


Photos: Getty

Britney and potty mouth, Irish actor Colin Farrell met when she visited the set of his movie S.W.A.T. back in 2003.  The next week the two were strolling down the red carpet hand-in-hand during the premiere of his movie The Recruit. The pair was seen hugging and kissing on two occasions at different nightclubs. It was short-lived and Colin claimed Britney was “just a mate.”

5. 50 cent and Chelsea Handler

Another head scratcher, 50 Cent and Chelsea Handler began dating after Fiddy was a guest on her show Chelsea After Dark in 2011. The rapper pursued her, which led to a several month long romance that abruptly ended later that year over an issue involving his ex, singer Ciara.

6. Tom Cruise and Katie Holmes

Photo: Sean Thorton/

Okay, everybody thought this was weird, right? All of a sudden a 44-year old Tom Cruise was jumping on couches telling the world how much he loved 26-year old Katie Holmes. Just weird, and it only got weirder. After 5 years of Scientology marriage the couple divorced in summer 2012.

7. Madonna and  Dennis Rodman

Photo: Andrew D. Bernstein/NBAE via Getty Images

This relationship is definitely strange, but it would be a lot stranger if Madonna wasn’t such a weird cookie herself. Dennis and Madonna dated for 2 months in 1994. Weirder still, Rodman was once married to Carmen Electra.

8. Tom Cruise and Cher

Photo: MCaulfield/WireImage

That’s right, kids, long before there was a Tom and Katie there was Tom and Cher. The two had a brief romance in 1985 when she was 39 and he was just 23.

9. Macaulay Culkin and Mila Kunis

Photo: WENN

Who knows how these two ended up together but they were in a long-term relationship for 9 years! The couple was reportedly engaged but split in 2011.

10. Michael Jackson and Lisa Marie Presley

Photo: Nikki Nelson/

The King of Pop marries the daughter of the The King. Makes sense, yet this was still an odd pairing to many people. The two were married from 1994-1996.

11. P. Diddy and Cameron Diaz

Photo: Getty Images

Life and Style magazine reported that the two were seen “making out and acting romantic” back in December 2011. The rumor of their relationship continued into the next year.

12. Justin Timberlake and Fergie

Photo: Getty Images

Yeah, we didn’t know either! The two urban hit makers dated back in 1997 when Justin was just 16 and Fergie was 23. She reportedly admits to the relationship, though, she regrets it now due the age difference. Her friends used to call her “Stella” (as in How Stella Got Her Groove Back).

13.  Flava Flav and Brigitte Nielson


Photos: Getty

Flav and Brigitte, who was once married to Sylvester Stallone and admitted to having an affair with Arnold Schwarzenegger, met on the reality show The Surreal Life in 2004. The pair began an odd and volatile relationship that lasted for almost 2 years.

14. Ryan Gosling and Sandra Bullock

Photo: Getty

It might be an odd pairing, but we can’t blame Sandra for wanting her some Ryan Gosling. They started dating during filming of the 2002 movie Murder By Numbers. They dated for a year. Bullock’s friend, and fellow actor Hugh Grant used to refer to Ryan as “The Child.” Gosling is 16 years her junior! And get this, he says til this day that she and former flame Rachel McAdams were the “best girlfriends ever.”

15. Mariah Carey and Nick Cannon

Photo: WENN

What is there to be said about these two? Mariah wanted her a boy toy; Nick filled the role. We all thought we were getting punk’d but then they got married in 2008 and had twins in 2011. Ten year age gap between these two, in case you were wondering.

  • ivvie


  • Kitty La Rue

    I would have never guessed Mila Kunis dated M.Kulkin.

  • Sally

    I hate that half this list is interracial couples…It definitely feels like they’re being singled out, and there’s nothing so “weird” about Puff Daddy/Diaz or Rihanna/Josh Harnett. People who think that are just purely reacting to race.

    • MadHatter89

      Yup, I noticed that too! There have definitely MUCH weirder couples than these, but this writer seems to want to make it look like interracial dating is weird.

    • toutedelafruit

      It’s not “weird” because she’s black and he’s white, it’s “weird” because (from the publics point of view…of not knowing anything real about them) they, seemingly, have absolutely nothing in common.

      On an unrelated note: this website reads as if it was run by a middle-schooler.

    • Jimmy

      Yes it Is weird. These white chicks with these filthy kneegrows!

  • MadHatter89

    What’s so weird about Rhianna and Josh Hartnett? It seems like they actually liked one another, and he didn’t seem to be abusive to her like Brown. I was hoping that they would stay together.

  • JokersGirl

    It really does not matter weather the public knows anything about them or that they do not have anything in common. It has nothing to do with that so you just made yourself sound not right at all for saying, typing, and even posting that comment.

  • james

    Seriously, how come no one has mentioned Taylor Kinney and Lady GaGa? Now that is a truly bizarre match. It makes you wonder what is wrong with a guy like that for him to date an attention seeking mess? This is not anything about her music, talent etc.

    • lilith

      maybe she has a great personality

StyleBlazer is a fashion and beauty website dedicated to edgy, progressive, chic and globally-minded women. Topics covered on StyleBlazer include street style, trends, expert beauty advice, and industry news.