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Top 10 Unlikely Celebrity Couples

VO: Rebecca Brayton
Script Written by Matthew Thomas Sometimes opposites truly do attract. Join WatchMojo.com as we count down our picks for the top 10 unlikely celebrity couples. For this list, we’ll be looking at couples where both members are famous, but who don’t seem to go together based on a discrepancy in their ages or seemingly clashing public personas. Special thanks to our users Javontay Mcelroy, toddlerss, Temika Singletary, Avvi Guitar and PowerCosmic901 for submitting the idea through our Suggest Tool at WatchMojo.comSuggest
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Script Written by Matthew Thomas

Top 10 Unlikely Celebrity Couples


Sometimes opposites truly do attract. Welcome to WatchMojo.com, and today we’re counting down our picks for the top 10 unlikely celebrity couples.

For this list, we’ll be looking at couples where both members are famous, but who don’t seem to go together based on a discrepancy in their ages or seemingly clashing public personas.

#10: Flavor Flav & Brigitte Nielsen

When these celebrity oddballs met in 2005 during “The Surreal Life’s third season, the connection they shared epitomized the show’s title. Flav was known best as a member of the politically active hip hop group Public Enemy, and Brigitte’s major claim to fame was her onetime marriage to Hollywood heavyweight Sylvester Stallone. Aside from their very different backgrounds, the height difference between the 6’2” Nielson and 5’5” Flav – along with the outrageous fashion sense they shared – gave the couple quite the visual flair, as seen on their reality show “Strange Love.” You got that right.

#9: Sandra Bullock & Jesse James

One of two women on this list known as America’s Sweetheart, Sandra’s sweet demeanor and traditional beauty are the opposite of the man who became her husband. James, known mostly for his West Coast Choppers brand and heavily tattooed, intense persona, seemed to be trading up when he replaced his previous porn-star wife with the A-lister in 2005. But, that didn’t stop him from cheating, and the couple split amid a scandal in 2010. This was not the first surprising coupling for Bullock, who’d previously dated her much-younger co-star Ryan Gosling.

#8: Julia Roberts & Lyle Lovett

America’s other Sweetheart; Julia Roberts was one of the most recognizable stars in the world – even in the early-‘90s – and she’d been in a string of relationships with Hollywood leading men like Liam Neeson, Jason Patric and Kiefer Sutherland. Then seemingly out of nowhere, in 1993 she was married to the awkward looking country star Lyle Lovett. Despite being cruelly dubbed by the press as “beauty and the beast,” Roberts stood by her husband. That is, until career commitments split to two up less than 2 years after they wed.

#7: Russell Brand & Katy Perry

Describing himself as an “S&M Willy Wonka,” Brand was the British bad boy. Admitting publically that he was a sex and substance abuse addict and that he masturbated a stranger in a public bathroom for research, it was odd to picture him in a committed relationship at all. The fact that, in 2010, he actually married pop star Katy Perry, whose image wasn’t squeaky clean but didn’t seem to have any connection to the world he lived in, was all the more shocking. Unfortunately, this odd couple didn’t last, and their divorce was finalized in 2012.

#6: Madonna & Dennis Rodman

By the mid-‘90s, Madonna had taken her already-edgy persona to new extremes. She’d released a book that featured images of the singer in a variety of sexual situations, a movie that featured S&M and bondage, and she’d gone off on an explicit tirade on a late-night talk show. All of this fed the public sentiment that she’d gone too far and that her career may be over because of it. Enter Mr. Rodman. The undisputed controversy lightning rod of basketball at the time, Rodman’s extreme fashion choices and outrageous behavior were crazy enough that people were shocked to see Madonna with him in 1994. The relationship didn’t last.

#5: Demi Moore & Ashton Kutcher

At one time the highest paid woman in the entire movie industry, Demi Moore built a reputation as a force to be reckoned with, which made it all the more unexpected that she’d date and marry a doofus 15-years her junior. Even before they wed in 2005, the couple was everywhere – especially on twitter – where they’d routinely post images of their lives like a couple of high schoolers, not movie stars and business people. Despite Demi’s kids and ex-husband Bruce Willis embracing Kutcher and melding their lives together, this relationship came to an end in 2011 amid rumors he’d been unfaithful.

#4: Tom Cruise & Cher

The fact these two were ever a thing has been all but forgotten. He moved on to marry Mimi Rogers, Nicole Kidman and Katie Holmes, and she went on to date a number of men but never did quite find the right one to settle down with. Aside from the 16-year age difference, Cher’s notoriously extreme style and persona while they were together was the opposite of Cruise’s jocky, pretty boy image. Though the two have rarely spoken about their time together, we’d still love to know how these two became intertwined in the mid-‘80s.

#3: Lance Armstrong & Ashley Olsen

Born 15-years apart, there is nobody who could’ve predicted this celebrity pairing – especially since it predated sister Mary-Kate’s relationship with the also much older Olivier Sarkozy by several years. The controversial seven-time Tour de France winner and the squeaky clean former child star were seen kissing and flirting on several occasions in 2007 before they publicists and friends convinced the two to distance themselves from each other. In fact, a 2014 book called “Cycle of Lies” claimed that Armstrong ended the fling because he feared his image would be tarnished.

#2: Gene Simmons & Diana Ross

When a man whose stage persona is called The Demon becomes romantically entwined with a woman who was considered one of the most refined and elegant women in the world, it was bound to surprise many. When that man also happens to be known as a shameless womanizer who claims to have bedded 4,600 women, it becomes absolutely shocking. We assume the couple parted ways when Simmons’ eye started to wander again, but we won’t forget about their time together in the early-‘80s anytime soon.

Before we unveil our top pick, here are a few honorable mentions:
- Roger Ebert & Oprah Winfrey
- Drew Barrymore & Tom Green
- Mila Kunis & Macaulay Culkin
- Marilyn Manson & Evan Rachel Wood
- Seal & Heidi Klum
- Zac Efron & Michelle Rodriguez

#1: Michael Jackson & Lisa Marie Presley

The King of Pop and the King of Rock’s daughter getting married may make sense on paper. In reality, these two could not have seemed more different and less connected to outsiders. She was the recently divorced daughter of a legend who had never fully embraced the attention her parentage had brought her. He was an amazing musician whose odd behavior, ever-changing face and legal troubles ensured he was the most photographed star in the world. When they chose to appear publically for the first time at the 1994 MTV Video Music Awards to share an awkward kiss that lacked both chemistry and passion, people’s perception of the pair as the ultimate odd couple was cemented.

Do you agree with our list? Who do you think is the least likely celebrity couple? For more pop culture Top 10s published daily, be sure to subscribe to WatchMojo.com.
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