couples The Oddest Celebrity Couples in Recent Memory  

Lisa Waugh
70.9k votes 5.3k voters 510.9k views 40 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 find it difficult to date mere mortals. When you’re high profile, 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 catch on fire 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 or Rachel Even Wood and Marilyn Manson. But then there are the super nova weird Hollywood couples such as Edward Norton and Courtney Love, and Billy Corgan and Tila Tequila. We may not know the reasons why these famous couples got together, but we do know that Adam Duritz and David Spade were getting all of 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/via Twitter
27-year-old 90210 actress Jessica Lowndes revealed that she was dating 57-year-old comedian and actor Jon Lovitz in the spring of 2016. Lovitz is 31 years older than Lowndes. What's more surprising: Their age difference or the fact that Lovitz can still land hot, young, and relatively successful chicks?

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Courtney Stodden & Doug Hutchison

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Video: YouTube

Hutchison wasn’t a celebrity until he married a 16-year-old virgin. The 51-year-old character actor met the highly-ambitious Stodden online. After a bit of a courtship, her parents gave the actor consent to marry their daughter. Stodden and Hutchison split up three years later due to their 35-year 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. It’s the look at 2:39. Stodden’s dad is four years younger than Hutchison.

Source: Huffington Post
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Mary-Kate Olsen & Olivier Sarkozy

Mary-Kate Olsen & Olivier ... is listed (or ranked) 3 on the list The Oddest Celebrity Couples in Recent Memory
Photo: via Reddit

When fashion designer and former Full House darling Mary-Kate Olsen was seen cozying up to the brother of the former president of France, people balked. They seemingly come from two 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.

Photo: Hello Magazine
Source: Mirror
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Jennifer Aniston & Adam Duritz

Jennifer Aniston & Adam Du... is listed (or ranked) 4 on the list The Oddest Celebrity Couples in Recent Memory
Photo: via Twitter

This odd couple is even odder now. Aniston was a hot star in 1995, thanks to Friends, and Counting Crows was a big time band. Duritz dated Aniston’s Friends costar and bestie Courteney Cox just before pairing up with her. Duritz defended his seemingly shady move by saying, “We never even slept together.”

Source: US Magazine
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