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20 Weirdest Musical Duos

Billy Ray Cyrus & Lil Nas X

Country music star Billy Ray Cyrus and rapper Lil Nas X may seem like an unlikely duo, but they managed to produce one of the biggest hits of 2019--“Old Town Road”. 

This version, which is actually a remix of the original, got its start when Cyrus’ wife, Tish, played the song for him. Even though Cyrus may not have any history with rap, he loved the song immediately, and the rest is history! 

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Eminen & Elton John

You would be hard pressed to find two musicians that are more different than Eminem and Elton John. From their music to their personalities, the two are like oil and water. But when they got together for a Grammy performance in 2001, it was magic. 

The two performed Eminem’s then-recent hit, “Stan”, and to the shock of everyone listening, it was actually a great performance. It wasn’t what we were expecting, but it was clearly what we needed. 

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Bing Crosby & David Bowie

At his peak, Bing Crosby was known as a charming, family-friendly crooner. David Bowie? Not so much. But that’s only half of what makes their collaboration weird. 

What’s really strange about this pairing is the song they picked to sing--“The Little Drummer Boy.” Granted, it was for Crosby’s Christmas special, but we have a hard time imagining Bowie belting out holiday hits at any time of the year. 

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Lou Reed & Metallica

Taken separately, Lou Reed (of The Velvet Underground) and Metallica are obviously iconic. So a merging of these musical talents is sure to be out of this world, right? Not so fast. 

In 2011, Reed and Metallica teamed up to release Lulu--a concept album that saw Reed reciting spoken word bits over Metallica’s backing. Fans from all sides of this collaboration found the album to be perplexing and just downright bad. 

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Dolly Parton & Sylvester Stallone

Dolly Parton may objectively be the best musician to ever live, but even she couldn’t save this bizarre, terrible duet with...Sylvester Stallone? 

The two were both starring in the 1984 comedy, Rhinestone, and some producer clearly thought they needed a musical number--“Sweet Lovin’ Friends”. That producer thought wrong. In addition to the movie doing terribly, the song itself “won” a Razzie award in 1985. 

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Ozzy Osbourne & Miss Piggy

If there’s anyone in the world who knows how to keep the Prince of Darkness in check, it’s Miss Piggy. And when Osbourne appeared on The Muppet Show to sing a duet with her, it just worked. 

The two performed “Born to Be Wild”, and like every Muppet/Musician duo, it was immediately a charming hit. 

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Paul McCartney & Stevie Wonder

When Paul McCartney & Stevie Wonder got together to record a version of “Ebony & Ivory” in the 80s, they thought it was a match made in heaven. And so did listeners--it hit the top of the charts in 1982. Future listeners found it much more weird, however. 

These days, the duet is considered bizarrely cheerful and has frequently found itself on lists of the worst musical duos of all time. 

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Frank Sinatra & Bono

Frank Sinatra is one of America’s most iconic musicians, and in 1993 he released an album of duets with other singers. Many of his collaborators made sense--it included the likes of Barbra Streisand and Tony Bennett. However, one name on the list was highly strange: Bono. 

The two released a version of “I’ve Got You Under My Skin”, and things did not go well. Apparently Sinatra was not a fan of Bono’s earring--and we’re inclined to agree. 

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Gwyneth Paltrow & Huey Lewis

Huey Lewis is known for being a world-class singer and songwriter. Gwenyth Paltrow is best known for trying to sell us new age garbage. And when you put the two together, you get a duet that’s as bizarre and terrible as you think it is. 

The two did a cover of the Smokey Robinson song “Cruisin’” for the 2000 karaoke-themed movie “Duets.” Unsurprisingly, both the film and the cover were widely panned. 

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Tim McGraw & Nelly

Country and rap may seem like two genres that shouldn’t mix, but Tim McGraw and Nelly proved everyone wrong in 2004 with their hit single, “Over and Over.” 

The song was an international hit, so much so that the duo reunited for a Budweiser commercial in 2005. They may make different music, but they both speak the same language: money. 

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Amy Winehouse & Tony Bennett

Amy Winehouse was a music icon in her own right, but the idea of her performing a duet with Tony Bennett just sounded weird. And that’s because it was weird. 

The two sang “Body and Soul” on Bennett’s 2011 album of duets, and judging from the video, the late Winehouse was struggling to keep it together. It would be her last recording before dying by alcohol poisoning. 

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Snoop Dogg & Tupac

This is a memorable (and weird) collaboration because it’s quite possibly the only duet to ever be performed from beyond the grave. 

In 2012, Tupac Shakur, who had died 16 years earlier, took the stage at Coachella as a hologram with still-alive musician Snoop Dogg. This is definitely one of the weirder duets out there, but it’s also incredibly impressive, considering the technology involved. 

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Boy George & Luther Vandross

Luther Vandross was an R&B legend. Boy George is gender-bending pop icon. It might not seem like the two have much in common, but when the two got together, the results were surprisingly good. 

Vandross and George famously performed the 60s ballad “What Becomes of the Brokenhearted” at the Apollo Theater in 1985. Despite a little alleged backstage drama, the two managed to pull off an impressive performance of this hit. 

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Tina Turner & Bruce Willis

Normally when you pair a singer (even a great like Tina Turner) with an actor, the results are dreadful. But she wasn’t paired with just any actor, she was paired with Bruce Willis--who is a decent musician in his own right. 

Much to the surprise of everyone there, Turner brought out Willis and his band, The Accelerators, for a performance of “Unfinished Sympathy” during her 1996 Wildest Dreams tour. It was by no means the best performance ever, but it was neat seeing such an unlikely duo have so much fun on stage. 

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David Bowie & Mick Jagger

At first glance, rock icons David Bowie and Mick Jagger seem like a perfectly reasonable pairing. And that’s because they are. The weird part about their collaboration was the song itself. 

In 1985, the two released a cover of “Dancing in the Street”, complete with a music video--and boy was it bizarre. It features the two singing and dancing in the most unnatural, high-energy way you can imagine. But regardless of its weirdness, the duet it still considered one of the best to this day. 

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Eddie Murphy & Michael Jackson

Even though it sounds ridiculous, Eddie Murphy tried to make it as a musician at one point. While he was by no means good, he was at least famous enough to get Michael Jackson on board for a song on his third album. 

To nobody’s surprise, the singe--“Whatzupwitu”-- was a flop, and the accompanying music video is still considered one of the worst of all time. It may not have been Michael Jackson’s worst life choice, but it was definitely a terrible musical choice. 

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Busta Rhymes & Ozzy Osbourne

Ozzy Osbourne is not afraid to step out of his musical comfort zone--as evidenced by the fact that he makes multiple appearances on this list. So when rapper Busta Rhymes gave him a call to work on a new track, he definitely said yes. 

The song was “This Means War”, and it featured the iconic “Iron Man” riff. Rhymes brought in Osbourne to sing on the chorus, and while Ozzy had never done rap before, he said that he loved it and wanted to try more. 

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Cher & Beavis & Butthead

We’re not quite sure what would make Cher want to collaborate with Beavis and Butthead, but she clearly wasn’t in a good place when she agreed to cover “I Got You Babe” with them. 

There probably isn’t much crossover between Cher fans and Beavis and Butthead fans, but this rendition surely delighted someone out there. For the rest of us, it left us scratching our heads. 

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Pet Shop Boys & Dusty Springfield

The Pet Shop Boys lived and breathed synth pop. Dusty Springfield was a soulful singer. Could this unlikely British pairing make it work? Absolutely!

The group recorded “What Have I Done to Deserve This?” in 1987, and it flew up the charts in both the UK and the United States.

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Cat Stevens & Ozzy Osbourne

Despite not having much in common musically, Ozzy Osbourne and Cat Stevens do both have hit songs with “train” in the title. This was apparently enough to warrant a duet between the two. 

This unlikely pair performed their “Peace Train”/”Crazy Train” rendition at Jon Stewart’s Rally to Restore Sanity and/or Fear, which is a relief because laughter is the only correct response to this silly mash-up. 

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