Celebrity Couples The Oddest Celebrity Couples In Recent Memory  

Lisa Waugh
377.9k votes 28.6k voters 2M views 42 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 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 or Rachel Even Wood and Marilyn Manson. 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: @realjonlovitz/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.

Also Ranked

#82 on The Funniest People of All Time

#21 on The Best SNL Cast Members of All Time

#30 on The Most Successful Saturday Night Live Alumni

#6 on The Best SNL Cast Members of the '80s

More Jon Lovitz

The Best Jon Lovitz Movies
12,048 1,928
Is this a weird couple?
2 13,026 VOTES

Courtney Stodden And Doug Hutchison

Ranker Video
Video: YouTube

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.

11,071 1,955
Is this a weird couple?
3 14,160 VOTES

Mary-Kate Olsen And Olivier Sarkozy

Ranker Video
Video: YouTube

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.

10,473 3,687
Is this a weird couple?
4 13,201 VOTES

Jennifer Aniston And Adam Duritz

Jennifer Aniston And Adam Duri... is listed (or ranked) 4 on the list The Oddest Celebrity Couples In Recent Memory
Photo:  Pimkie/Flickr/Taylor Spaulding/Flickr/CC BY-SA 2.0

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 his seemingly shady move by saying, “[Aniston and I] never even slept together.”

9,756 3,445
Is this a weird couple?