relationships The Oddest Celebrity Couples in Recent Memory  

11.5k votes 1.3k voters 263.3k 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.
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Benji Madden & Cameron Diaz

Benji Madden & Cameron Dia... is listed (or ranked) 1 on the list The Oddest Celebrity Couples in Recent Memory
Photo: via Tumblr
Billboard and many other media outlets thought this was an odd pairing. There are only six years in age difference,  but many bookies wouldn’t have put these two together. Guess who did? Nicole Richie. Richie is married to Madden’s twin brother Joel and wanted her brother-in-law to be as happy as his brother was, so she set Diaz and Madden up on a date.

Photo: Pop Sugar
Sources: BillboardFashion Times
342 185

David Spade & Julie Bowen

David Spade & Julie Bowen is listed (or ranked) 2 on the list The Oddest Celebrity Couples in Recent Memory
Photo: via Tumblr
Apparently, David Spade has serious game. He’s dated Heather Locklear, Nicolette Sheridan, Lara Flynn Boyle, Pamela Anderson, and has a child with former Playboy playmate Jillian Grace. But it’s the Spade/Julie Bowen pairing that caused E! Online to use the words “surprising.”

Source: E! Online
273 145

Michelle Rodriguez & Zac Efron

Michelle Rodriguez & Zac Efron is listed (or ranked) 3 on the list The Oddest Celebrity Couples in Recent Memory
Photo: via Tumblr
M-Rod’s sexual experimentation was not the surprise when she rolled up with Zac Efron. Her relationship with Cara Delevingne was quite public. But when Efron and Rodriguez appeared to be an item, the world had a meltdown with every major media outlet doing a collective double take. And then, there was a huge wave of support, where media and fans alike were rooting for the couple. But it didn’t last. Rodriguez has never committed to being gay and has said, “I’ve gone both ways. I do as I please. I am too curious to sit here and not try when I can. Men are intriguing. So are chicks.”

Photo: Pop Sugar
Source: Radar
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Ryan Reynolds & Alanis Morissette

Ryan Reynolds & Alanis Mor... is listed (or ranked) 4 on the list The Oddest Celebrity Couples in Recent Memory
Photo: via Tumblr
Isn’t it ironic? Doncha think? Reynolds seems to have a type and Morissette refreshingly didn’t fit his later Scarlett Johansson/Blake Lively profile. Fans and media outlets couldn’t quite wrap their heads around the A-list actor and the more-popular-in-the-'90s singer getting engaged in 2004. This was no fly-by-night celebrity couple, though. They stayed together for five years. Morissette’s album Flavors of Entanglement was said to have been inspired by the break-up.

Photo: vh1