12 of the Most Unlikely Duos in Entertainment History

12 of the Most Unlikely Duos in Entertainment History

The proverb “oil and vinegar don't mix” is a way of saying that certain people or things don't go together, but they must clearly mean they don’t physically fuse together, because every Italian restaurant’s appetizer will tell you, they definitely mix taste-wise. So you can see how confusing it is. So, whether these unlikely partnerships “tasted good” or not is up to you. All we know is… They were straight up strange. 

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We’re not ones to knock creative experimentation, but what in the good god damn was Sylvester Stallone doing singing country with Dolly Parton?! Some sort of line was crossed on that one for sure! Man, the ‘80s were a weird time. The “odd couple” trope in comedies and buddy cop movies can be pretty awesome. We get all those sweet “fish out of water” jokes from both characters who can’t even comprehend the others’ background and point of view. They’re not all gems, but it seems to work overall. Music though… Those “odd couple” collabs can go out on a literal bad note, like a whole bunch of these 12 unlikely duos in entertainment history.

And we all just thought he was the party anthem guy!

CRACKED ANDREW W.K.'S RADIO SHOW ON GLENN BECK'S NETWORK. In 2015, he hosted a free-form radio show called America W.K. on Glenn Beck's conservative-leaning network, The Blaze. Не covered topics like depression, the human spirit, and his experience almost becoming U.S. cultural ambassador to Bahrain.

Vanity Fair

Not just one song, an entire movie and the soundtrack!

CRACKED DOLLY PARTON AND SYLVESTER STALLONE The 1984 film Rhinestone was written by Stallone and stars himself and Dolly Parton. Even stranger, Stallone sings country music with Parton on 4 tracks of the soundtrack. Listen to his country accent. Please. It's mind-boggling.

Wikipedia / IMDB 

Yeardley Smith got deep into the true-crime realm.

CRACKED LISA SIMPSON AND THE GUY WHO CAUGHT THE GOLDEN STATE KILLER. Paul Holes, an investigator best known for his Golden State Killer-catching, joined Yeardley Smith's hit true-crime podcast Small Town Dicks as a co-host.

Nerds and Beyond

We’re pretty sure Dido never once thought Eminem would help launch her music career.

CRACKED EMINEM & DIDO Eminem's Stan uses English singer Dido's single Thank You as the chorus between his dark verses. The 8-minute video featured Dido as Stan's girlfriend, and it helped her album No Angel sell 21 million copies worldwide. KORG

American Songwriter / NME 

Quick… What do Method Man and a Scottish soft rock band have in common?

CRACKED TEXAS AND THE WU-TANG CLAN Not the state, the Scottish soft rock band said We were massive fans of the Wu. The RZA said Sharleen Spiteri's vocals were like a sample that worked well with my dark, grainy production. Method Man and Texas recorded the song Say What You Want.

The Guardian

This one puts a smile on our faces.

CRACKED SNOOP DOGG & MARTHA STEWART Snoop was a guest on her show in 2008, and their chemistry was a hit. It sparked a friendship and appearances like the Justin Bieber roast, the game show $100,000 Pyramid, and their joint cooking show on VH1, Martha & Snoop's Potluck Dinner Party.


Bizzy, Wish, Layzie, Krayzie, and Flesh-n-Bone added some Chrome!

CRACKED PHIL COLLINS AND BONE THUGS-N-HARMONY When Bone Thugs sampled Phil Collins' track Take Me Home for their 2003 song Home, Collins appeared in the group's video and they made him an honorary member, with the moniker Chrome Bone.

AV Club / Youtube 

Why, damnit? Why?!

CRACKED OZZY OSBOURNE AND JESSICA SIMPSON They performed Winter Wonderland for The Osbourne Family Christmas Special on MTV in 2003. A Christmas song by Ozzy is weird enough, but his vocals alongside Jessica Simpson's are downright un-listenable.


And, as you guessed it, the songs are incredibly strange.

CRACKED YOKO ONO & THE RZA In 2010, they performed duets on Seed of Joy/Life is a Struggle and Greenfield Morning I Pushed An Empty Baby Carriage All Over The City from the album Yoko Ono/Plastic Ono Band. EAR

Fact Mag / Youtube 

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