We’re obsessed with celebrity couples. Can you blame us? Imagine being rich, famous, and having your pick of attractive partners. We like to think we know who our favorite entertainers would pair best with, but time and time again, reality has proven us wrong…or has it? There have been more than a few bad matches, odd couples, and unholy matrimonies over the past two decades, and we’ve been witness to them all. These are our 20 least favorite celebrity couples of the past 20 years, ranked!
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Least Favorite Celebrity Couples
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20. Ryan Reynolds and Alanis Morissette
Being Canadian and famous were the only things these two seemed to have in common.
Photo: Jeff Kravitz/FilmMagic (Getty Images)
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19. Ben Affleck and Jennifer Lopez
Mostly we’re still mad that Bennifer made – and made us watch – Gigli.
Photo: Kevin Winter (Getty Images)
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18. Gwyneth Paltrow and Chris Martin
Truthfully, we didn't mind these two so much when they were together. It was their holier-than-thou "conscious uncoupling" that made us lose our cookies.
Photo: Kevin Mazur (Getty Images)
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17. Taylor Swift and Tom Hiddleston
He's such a classy Brit and she's such a loudmouth American. These opposites attracted, though, for a while.
Photo: starzfly/Bauer-Griffin/GC Images (Getty Images)
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16. John Mayer and Jessica Simpson
The idea of Mayer being with any woman (and serenading her with “Your Body Is a Wonderland”) is enough to make us lose our lunch, but this pairing with another subpar singer was particularly awful.
Photo: Kevin Mazur/WireImage (Getty Images)
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15. Blake Shelton and Gwen Stefani
These two are so into each other it makes us want to puke in a 10-gallon hat.
Photo: Patrick McMullan/Patrick McMullan (Getty Images)
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14. Tom Cruise and Nicole Kidman
We know now that she was way too good for him. Did she know then?
Photo: Vinnie Zuffante (Getty Images)
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13. Lena Dunham and Jack Antonoff
Could there be a more obnoxious pair on the planet? We think not.
Photo: Jeff Kravitz/FilmMagic (Getty Images)
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12. Michael Douglas and Catherine Zeta-Jones
The only solace we take in this coupling is that he will certainly die first and then she can marry someone her own age.
Photo: Earl Gibson III (Getty Images)
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11. Ashton Kutcher and Demi Moore
Mommy issues much?
Photo: Chris Polk/FilmMagic (Getty Images)
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10. Britney Spears and Justin Timberlake
No, we don't want to know what happened with Britney Spears' virginity while you two were together. Thanks.
Photo: Kevin Mazur/WireImage (Getty Images)
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9. Pete Davidson and Ariana Grande
It's clear that Davidson has no idea what to do with her. And we don't blame him.
Photo: Jamie McCarthy (Getty Images)
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8. Selena Gomez and Justin Bieber
These two looked like a couple of kids pretending to be adults and their relationship was just as immature as you'd think it was.
Photo: JB Lacroix / Contributor (Getty Images)
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7. Tyga and Kylie Jenner
Beauty and the beast?
Photo: Craig Barritt (Getty Images)
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6. Katy Perry and Russell Brand
We all saw this train wreck coming a million miles away, right, guys?
Photo: Charley Gallay/WireImage (Getty Images)
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5. Angelina Jolie and Billy Bob Thornton
This PDA-loving couple made us gag in more ways than one on many a red carpet during their courtship and marriage.
Photo: Gareth Davies (Getty Images)
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4. Pamela Anderson and Kid Rock
Apparently, Anderson didn’t learn her lesson about musicians making for bad husbands because she picked up this piece of white trash less than a decade after divorcing rocker Tommy Lee.
Photo: ERIC ESTRADE/AFP (Getty Images)
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3. Marilyn Manson and Evan Rachel Wood
Anyone who hooks up with a 19-year-old while still married to another woman is too creepy to live, much less love.
Photo: John Shearer/WireImage (Getty Images)
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2. Mary-Kate Olsen and Olivier Sarkozy
See that terrified look in her eyes? We feel exactly the same way about their 17-year age difference.
Photo: James Devaney/WireImage (Getty Images)
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1. Woody Allen and Soon Yi Previn
When a man marries his partner's adopted daughter, he really should be banned from Earth for life.
Photo: Venturelli/WireImage (Getty Images)
