Celebrity Odd Couples: The Most Mismatched Hollywood Pairs Over The Years

August 21, 2013  |  
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Celebrity Odd Couples

Paula Abdul made a very valid point in her hit 1989 song: opposites do attract. Here’s a look at some of the celebrity odd couples who have been paired up over the years.

"Woody Allen and Soon-Yi pf"


Woody Allen thought he’d found happiness with partner Mia Farrow back in the day. Although the pair never got married or lived under the same roof, they did adopt children together, which is why it was a shock to Hollywood and everyone else in 1992 when Allen split up with Farrow and started dating one of her adopted daughters, Soon-Yi, who was around 19 years old at the time — and 37 years his junior. After five years of dating, Allen made Soon-Yi his wife and they have been together ever since.

"Angelina Jolie and Billy Bob Thorton pf"


Like many other Hollywood couples, Angelina Jolie met her first husband Billy Bob Thorton while filming a movie together. After dating for a year, the two tied the knot in 2002. Despite the 19-year age difference, the married couple was known for their very, very public displays of affection. They even wore vials of each other’s blood around their necks. Too bad the marriage wasn’t meant to be. They divorced two years later.

celebrity odd couples


Back when Owen Wilson was an eligible bachelor, the Wedding Crashers star dated several people in the entertainment industry. One of the weirder hook-ups was with country singer Sheryl Crow. The two dated before going their separate ways in 2002. Wilson finally found love in Jade Duell, who gave birth to the couple’s son in 2011. Crow may still be single but she has her hands full with her two young adopted sons.

oprah roger ebert


Oprah Winfrey has been with her longtime beau Stedman Graham for over three decades. But before she set her sights on Graham, the talk show mogul went out on a few dates with fellow Chicagoan and budding film critic Roger Ebert. Even though the sparks didn’t fly, Ebert became Winfrey’s mentor. “Yes, it is true, I persuaded Oprah to become the most successful and famous woman in the world,” said Ebert.

"Brooke Shields and Andre Agassi pf"


Bad boy tennis star Andre Agassi was known for scoring aces on the court but off the court he scored with one of Hollywood’s leading ladies. Agassi started dating Brooke Shields in the early 90’s. By 1999, the two had tied the knot. Although opposites do attract, these two couldn’t make it last. They divorced two years later. Agassi is currently married to tennis great Steffi Graf while Shields and husband Chris Henchly have two children together.

"Matthew Broderick and Sarah Jessica Parker pf"


Matthew Broderick will always be the aloof teenager who played hooky from high school so it may seem out of place that he would hook up with one of the most influential and stylish women in Hollywood. In 1997, Broderick married Sarah Jessica Parker. The two met through her brother. Standing the test of time, the couple is still going strong and has three children together.



Who knew that late night talk show host Conan O’Brien used to date one of the “Friends” stars? Back when he was a writer for NBC’s “Saturday Night Live,” O’Brien dated Lisa Kudrow while she was still working as a comedian in Los Angeles. “He was really smart, really funny and he thought I was funny, but found we were better as friends,” Kudrow said of their brief romance.

"Robert Downey Jr pf"


Sarah Jessica Parker found love with her husband of 16 years Matthew Broderick but before she settled down with him, she was involved in another relationship that had people scratching their heads. From 1984 to 1991, Parker was in a serious relationship with Robert Downey, Jr., who was less than a perfect boyfriend to the “Sex and the City” star. “I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is,” Downey said.

"Alanis Morissette and Ryan Reynolds pf"


Alanis Morrisette may not seem like the type to date Hollywood actors but indie rocker dated one of the hottest guys in the entertainment industry and almost married him. In 2002, Morrisette began dating Ryan Reynolds. The Green Lantern star popped the question two years later. The couple split up briefly before giving it a go one more time. In 2007, Morrisette and Reynolds finally decided they weren’t meant to be and called it quits for good.

"Jennifer Love Hewitt and Joey Lawrence pf"


Even though she’s only 34, Jennifer Love Hewitt has had a long career in show business but she hasn’t had much luck in the love department. Back in the day as she was gaining attention from the hit show “Party of Five,” much to the chagrin of screaming teens everywhere, Hewitt dated heartthrob Joey Lawrence. The couple was together for a year in the mid 90’s. A congratulations is finally in order for Hewitt. Last month the “Ghost Whisperer” star announced she is expecting a child with her fiancé Brian Hallisay.

"Matt Dillon and Cameron Diaz pf"


There’s definitely something about Cameron Diaz. Actor Matt Dillon found that out when he started dating the blonde bombshell back in the mid 90’s. The couple dated for three years before calling it quits. The There’s Something About Mary co-stars actually split up just as the 1998 movie debuted on the big screen.

"Macaulay Culkin and Mila Kunis pf"


Who knew the cute, little scrappy kid from Home Alone would wind up with one of the most beautiful women in the world, according to People magazine. For almost a decade, Macaulay Culkin dated Mila Kunis. The couple almost made it down the aisle before breaking up in 2011. While Culkin has been spotted out in public looking frail recently, Kunis is currently involved with her “That 70’s Show” co-star Ashton Kutcher.

Dennis Rodman and Madonna


Madonna has always topped headlines. Whether it’s her outlandish outfits or controversial comments, the “Vogue” singer does what she wants so it really shouldn’t have been a huge shock when Madonna started dating NBA outcast Dennis Rodman back in the day. What is shocking is that she wanted to have his baby. The Chicago Bulls champion wrote in his I Should Be Dead By Now autobiography about his time with Madonna: “She just would do the weirdest things to make sure she was going to get impregnated by Dennis Rodman. It didn’t work. I’m pretty potent. I’m surprised.”

"Billy Corgan and Tila Tequila pf"


Musician Billy Corgan has been romantically linked with a few women that one could find shocking but none of them were quite as shocking as who he turned up with at the 2009 Bravo’s Second Annual “The A-List Awards:” Tila Tequila. Just as quickly as it began, the tryst with the one-time reality television show star ended. The Smashing Pumpkins member also dated Jessica Simpson and lived with Courtney Love for a couple years.

celebrity odd couples


Back in 1998, Meg Ryan’s relationship with Australian hunk Russell Crowe caused quite a stir. That’s because she was still married to fellow actor Dennis Quaid. Ryan met Crowe while on the set of the movie Proof of Life when her marriage was on the decline. “Dennis was not faithful to me for a very long time, and that was very painful,” Ryan told InStyle magazine. “I found out more about that after I was divorced. Russell didn’t break up the marriage.”

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  • Auri

    Wow, Eberts wife kind of look like a Oprah wanna be. I used to work at the rehabilitation institute where he was cared for. I didn’t like her very much. I saw her several times and she was so snobby!

  • MissOlivia

    As they say every moldy cheese have it moldy bread. We might find it odd but that moment it felt right for them.

  • mildredblack

    My last pay check
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  • enlightenment

    Are we going to ignore the fact that Woody Allen married his adopted daughter..?

  • Nene

    Singer Michel’le and Suge Knight.

  • Aaliyah Noelle

    How did macauglay pull mila? Omg shes beautiful
    Wow at first glance i thought that billy guy was pitbull hahahah

  • Lola

    u forgot about 50 cents and Chelsea Handler and Vivica Fox.. also Courtney Stodden and Doug Hutchinson, Ryan Gosling and Sandra Bullock, Nick Cannon and Mariah Carey, Eve and SStevie J..etc

    • Farrah

      How about Flava Flav and Bridget Neilson?

      • Lola

        it need to be flava flav and any body lol

        • enlightenment


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          • Lola


      • Nene

        They were my favorite couple.

  • Nicole Minor

    I guess they had nothing else to write about.

  • Alexis

    Madonna seem like the type to get obsessive just to try to have a baby by a black man.

  • Abbas BAKER

    There’s no such thing as odd couples. Where there is love, there is no oddity.

    • Nene

      Thank you. They may be odd to the world but to themselves they were/are perfect for each other.

  • Sebastion

    Angelina’s first husband was Johnny Miller not Billy Bob

    • Farrah

      Sherlock! Or Hackers, if you prefer 🙂

  • Momma Dee Tha Q.U.E.E.N

    Only i didnt kno about was Oprah & Ebert…

  • Madison

    “Odd couples” definitely describes this list!

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