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!

Vanity Fair

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

Wikipedia / IMDB 

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

American Songwriter / NME 

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

The Guardian

This one puts a smile on our faces.

Insider

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

AV Club / Youtube 

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

Fact Mag / Youtube 

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