19 Celebrity Odd Couples You Forgot All About

Celia San Miguel | Apr 10, 2016 Celebrities

Love is more unpredictable than the weather, and romantic attraction remains a mystery of human chemistry. These now-defunct and largely forgotten celebrity couples seemed like such unlikely pairings that their mere existence bewildered the masses. Some were tumultuous and short-lived, while others lasted years before going off the rails. 

From Emmy Rossum and Counting Crows' Adam Duritz to Drew Barrymore's mind-boggling marriage to comedian Tom Green, these romances prove that the heart wants what it wants — however odd it may seem to those on the outside looking in. 


Image via Walter McBride/Retna Ltd./Corbis

  • Drew Barrymore & Tom Green


    Image via Rune Hellestad/Corbis

    Apparently, a sense of humor does go a long way in winning a woman's heart. In 2001, Canadian funnyman Tom Green managed to get Hollywood darling Drew Barrymore to the altar. Behind closed doors, however, the giggles were apparently in short order: In December 2001, after nine month of marriage, Tom Green filed for divorce from Barrymore, citing irreconcilable differences. 

  • Halle Berry & Danny Wood


    Image via Larry Busacca/WireImage/Getty

    Once upon a time, Halle Berry thought New Kids on the Block's Danny Wood had "the right stuff." The two dated for a short period in 1989, when Berry was still a struggling actress hoping to make a name for herself in Hollywood.

  • Natalie Portman & Moby


    Image via Theo Wargo/WireImage/Getty

    How did self-professed nerd Moby manage to woo actress Natalie Portman? “I guess in some people’s eyes, [nerds] might be mildly sexy —and, as a nerd, I’m certainly happy to enjoy some of the effects of that," the musician told Spin magazine in reference to his fling with the Black Swan star in the early 2000s. According to Moby, he made some enemies while dating the face of Miss Dior. "It’s made me a target of a lot of nerd wrath — you don’t date Luke Skywalker’s mom and not have them hate your guts.” Poor baby!

  • Jennifer Love Hewitt & Jamie Kennedy


    Image via Frank Trapper/Corbis

    The Client List star Jennifer Love Hewitt has been linked to some of Hollywood's hunkiest men — from Antonio Sabato Jr. to Enrique Iglesias, John Mayer, and Wilmer Valderrama. But one of Love Hewitt's longer-lasting relationships involved an unlikely mate: comedian Jamie Kennedy, her Ghost Whisperer costar. From 2009 to 2010, they strolled down many a red carpet, hugging and smooching, fueling rumors of a possible engagement. By 2010, however, things fizzled. "People weren't rooting for a good relationship," Kennedy later told People magazine. "That was really hard to deal with." 

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  • Julia Roberts & Lyle Lovett


    Image via Frank Trapper/Sygma/Corbis

    Back in 1993, tabloids described newlyweds Julia Roberts and Lyle Lovett as "Beauty and the Beast."  But the Pretty Woman star clearly found her country singer hubby beautiful inside and out. According to reports at the time, the pair met only three weeks before getting hitched, and kept their impending nuptials under wraps, sending out invitations only 72 hours before the ceremony. On their wedding night, Roberts appeared on stage at a Lovett concert in Nobelsville, Indiana, and introduced her husband to the cheering crowd — all while wearing her white wedding dress. Busy schedules and long periods apart took a toll: They separated in 1995.

  • Whoopi Goldberg & Ted Danson


    Image via Mitchell Gerber/Corbis

    Cheers actor Ted Danson and Jumpin' Jack Flash comedienne Whoopi Goldberg shared much more than screen time while filming 1993's Made in America. When news of their unlikely dalliance surfaced, Ted Danson's marriage to producer Casey Coates ended in divorce. Their affair caused even more controversy in October 1993, when Danson appeared in blackface during a roast for Goldberg and proceeded to make a series of racist jokes as audiences cringed.

  • Ryan Reynolds & Alanis Morrissette


    Image via Frank Trapper/Corbis

    "We feel like we're already married," Ryan Reynolds said of fiancée Alanis Morrissette in 2005 (the couple started dating in 2002). The Deadpool star and the "You Oughta Know" singer never made it to the altar. The 2007 breakup was apparently a jagged little pill for Morrisette to swallow. Her 2008 album, Flavors of Entanglement, was reportedly inspired by the grieving process she underwent after the relationship came to an end.
  • January Jones & Josh Groban


    Image via Frank Trapper/Corbis

    As Betty Draper on AMC's Mad Men, January Jones was the first woman to captivate a young Don Draper. Off-screen, she's had a string of bewildering flings with the likes of Jim Carrey, Jeremy Piven, and Will Forte. But January Jones's nearly three-year-long relationship with singer Josh Groban, which ended in 2006, still figures among her most meaningful and long-lasting romantic entanglements. "We were madly in love," Groban told Details magazine in February 2013. "It was definitely my longest relationship."

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  • Flavor Flav & Brigitte Nielsen


    Image via Laura Farr/ZUMA/Corbis

    No one could have expected that sparks would fly between viking hat-loving Public Enemy hypeman Flavor Flav and Danish actress Brigitte Nielsen on the set of VH1's Surreal Life Season 3. And yet, their naughty hot tub moments and under-the-covers romps created such chatter that VH1 green lit a spin-off show centered on their relationship: 2005's Strange Love. Ultimately, Gita and Foofy Foofy said their goodbyes, as she chose her Italian boyfriend Mattia over Flav (shocker!). Was it all for the cameras? We may never know. 

  • David Spade & Julie Bowen


    Image via Branimir Kvartuc/ZUMA/Corbis

    Comedian David Spade, who played pervy office trickster Dennis Finch on Just Shoot Me!, must have some serious game! Over the years, David Spade has romanced such beauties as Heather Locklear, Nicollette Sheridan, and Modern Family star Julie Bowen. The two began dating in 2002 but parted ways after a year. Bowen wound up wedding her current husband Scott Phillips in 2004, and they have three children together. 

  • Emmy Rossum & Adam Duritz


    Image via Walter McBride/Retna Ltd./Corbis

    You can thank Twitter for bringing together Counting Crows frontman Adam Duritz and Shameless actress Emmy Rossum.  In July 2009, Rossum urged her Twitter users to follow "the incredible poet and singer Adam Duritz @countingcrows.” Flattered, Duritz — who was once linked to Jennifer Aniston — invited her to join the Crows on stage and perform a song, a dare she eagerly met. In November 2010, Rossum announced they had amicably split.

  • Nicolas Cage & Lisa Marie Presley


    Image via Phil Ramey/RameyPix/Corbis

    Elvis Presley super fan Nicolas Cage spoke about using The King as inspiration for his character in David Lynch's Wild at Heart, played an Elvis impersonator in the 1992 rom-com Honeymoon in Vegas, and bought The King's 1959 Cadillac Eldorado for his expansive car collection. So, when Cage married Lisa Marie Presley on August 16, 2002, some wondered whether he just wanted to feel closer to his idol. Whatever his or her motivations, Cage and Presley checked into the Heartbreak Hotel shortly after sharing vows, divorcing 108 days later.

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  • Rose McGowan & Marilyn Manson


    Image via Frank Trapper/Sygma/Corbis

    When Charmed star Rose McGowan strolled down the red carpet at the 1998 MTV Video Music Awards with ghoulish-looking Marilyn Manson, many scratched their heads in confusion. McGowan, however, was completely besotted with the shock rocker, accepting the Pale Emperor's marriage proposal in February 1999. The two never had their big metal wedding: In 2001, they split, with McGowan issuing a statement citing "lifestyle differences."

  • Lara Flynn Boyle & Jack Nicholson


    Image via 2000 Phil Ramey AGENCY/RameyPix/Corbis

    According to SNL alum David Spade, back in the late '90s, Jack Nicholson stole his then-girlfriend Lara Flynn Boyle, known for her work in The Practice. In fact, Spade says the Oscar-winning actor asked Boyle out right in front of him! However brazen, Nicholson's charm offensive was successful: By November 1999, he was spotted with Boyle, who was 33 years his junior, at industry events and LA Lakers games. By 2001, however, Boyle had decided dating Nicholson was not "as good as it gets."

  • Mila Kunis & Macaulay Culkin


    Image via Ethan Miller/Getty Images

    Before marrying her former That '70s Show costar Ashton Kutcher and giving birth to their first child, Wyatt Isabelle, Mila Kunis spent eight years in a low-profile relationship with Home Alone star Macaulay Culkin. The two broke up in late 2010 but kept the news quiet for months as Kunis promoted her film Black Swan, finally confirming the split in January 2011.

  • Brad Pitt & Juliette Lewis


    Image via  Frank Trapper/Sygma/Corbis

    Before Angelina, before ex-wife Jennifer Aniston, before his girlfriend of two years Gwyneth Paltrow, Hollywood leading man Brad Pitt dated actress Juliette Lewis. They began dating in 1990, when Pitt was an unknown, 27-year-old actor (his career-changing cameo in Thelma & Louise happened a year later), and Lewis was a 17-year-old ingenue with roles in The Wonder Years and National Lampoon's Christmas Vacation. "I was in my high school years, and it was a wonderful, loving relationship with a fun, smart guy," Lewis has said of her three-year romance with Pitt. "Then it was over, and he went on to become incredibly famous."

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  • Renee Zellweger & Jack White


    Image via Ronald Asadorian / Splash News

    Renee Zellweger sure likes musicians! The Bridget Jones star, who is currently dating singer-songwriter Doyle Bramhall II, was married to country crooner Kenny Chesney for four months in 2005. Zellweger's marriage to Chesney, however, may have been a rebound from her doomed relationship with White Stripes rocker Jack White. The two met on the set of Cold Mountain (White was writing music for the film, which landed Zellweger a Best Supporting Actress Oscar) and embarked upon a torrid and often turbulent romance that lasted from 2002 to 2004.  

  • Carmen Electra & Dennis Rodman


    Image via SGranitz/WireImage/Getty

    "People couldn't understand why I loved him because he had a reputation for being a bad boy," former Baywatch star Carmen Electra said about ex-husband Dennis Rodman, who she married in a Las Vegas Chapel in November 1998. "What I saw in the beginning was this gentle giant who was in a lot of pain so, in a way, we understood each other." The gentleness was short-lived: In 1999, both parties were arrested for allegedly assaulting each other during a domestic dispute. In March 1999, only six months into the marriage, Electra filed for divorce.

  • Ashley Judd & Michael Bolton


    Image via Tom Wargacki/WireImage/Getty

    Back in 1996, Ashley Judd and wavy-haired singer Michael Bolton were completely infatuated with one another. She even starred in his "The Best of Love" music video. Unlike in the song, however, their love did not grow stronger, nor did the best keep getting better — in fact, by 1997, they'd gone their separate ways. So much for life imitating art!

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