The Oddest Celebrity Couples In Recent Memory  

Lisa Waugh
379.5k votes 28.8k voters 2M views 43 items

List Rules Only couples that were together in 1990 or later. Couples do not have to currently be an item.

When you’re a celebrity, the dating pool gets pretty small pretty quickly because celebrities sometimes find it difficult to date mere mortals. When your profile is high, one does not simply swipe right and hope for the best, unless you are Adam Duritz. Because the industry is closed off, young actors make some rash mistakes, or the beer goggles were on during that yacht party, and the world ends up with some odd celebrity couples.

There’s chemistry and then there’s weird science chemistry. There’s also publicity. One up-and-coming star may hitch their wagon to a popular shiny one. Sometimes both weird celebrity wagons hit the curb and roll off a cliff, selling clicks and magazines across the nation. Strange celebrity couples always make the headlines. Remember that time Moby dated Natalie Portman? Or when Rosario Dawson dated Danny Boyle?

There are youthful mistakes such as Drew Barrymore and Tom Green. But then there are the supernova weird Hollywood couples such as Edward Norton and Courtney Love or Billy Corgan and Tila Tequila. We may not know why these famous couples got together, but we do know that Duritz and David Spade were getting all the hottest ladies at one point in time. Like we said, that dating pool can get small and crowded. No wonder it’s stocked with the oddest celebrity couples.

Who’s your favorite strange celebrity couple? Are you new-school or old-school? Or does weird not pay attention to eras? Upvote the oddest of the odd celebrity couples and be thankful your own relationships aren't on display.

Jon Lovitz is listed (or ranked) 1 on the list The Oddest Celebrity Couples In Recent Memory
Photo:  Jon Lovitz/Twitter

When she was 27, 90210 actress Jessica Lowndes revealed that she was dating 58-year-old comedian and actor Jon Lovitz in the spring of 2016. Days later, however, she revealed it was all a hoax.

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Courtney Stodden And Doug Hutchison
Courtney Stodden And Doug Hutc... is listed (or ranked) 2 on the list The Oddest Celebrity Couples In Recent Memory
Photo:  Glenn Francis /Wikimedia Commons/CC BY-SA 4.0

Doug Hutchison wasn’t much of a celebrity until he married a 16-year-old virgin. The character actor met the highly ambitious Courtney Stodden, 35 years his junior, online. After a bit of a courtship, her parents gave the actor consent to marry their daughter. Stodden and Hutchison wed in 2011. They split up in 2013 due to their age gap, but it didn’t last long. They got engaged in 2014, with Stodden saying that she had given other men a try and missed her husband.

Besides the age thing, it was Stodden’s hilarious behavior during an ABC interview that went viral. Stodden’s dad is four years younger than Hutchison.

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Mary-Kate Olsen And Olivier Sarkozy
Mary-Kate Olsen And Olivier Sa... is listed (or ranked) 3 on the list The Oddest Celebrity Couples In Recent Memory
Photo:  Gareth Wong/David Shankbone

When former Full House darling Mary-Kate Olsen was seen cozying up to the brother of the former president of France, people balked. The two seemingly come from different worlds and the 17-year age difference made this odd celebrity couple even stranger.

The French banker and the actress-turned-fashion designer married in 2015.

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Jennifer Aniston And Adam Duritz
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Video: YouTube

This odd couple is even odder now. Jennifer Aniston was a hot star in 1995, thanks to Friends, and Counting Crows was a big-time band. Adam Duritz dated Aniston’s Friends costar and bestie Courteney Cox right after.

Duritz defended this move by saying, “[Aniston and I] never even slept together.”

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