The 20 Most Awkward Music Collaborations

A cringeworthy look at artists who should've never worked together.

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Complex Original

Image via Complex Original

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LL Cool J and Brad Paisley sparked quite the controversy with their uncomfortable duet, "Accidental Racist," but when it comes to ill-advised collaborations, the country/rap hybrid is far from the worst. Over the years, we've seen everyone from Sting and Twista to Hilary Duff and Slim Thug link up in the name of music. We're all for taking risks and defying expectations, but mixing genres can definitely result in tragic consequences. Case in point: The 20 Most Awkward Music Collaborations. Read on and listen to what happens when people like Ja Rule and Metallica get on a track together. You're going to wish that these songs never happened.

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20. Willa Ford f/ Royce da 5'9" "I Wanna Be Bad" (2001)

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Prior to this remix, Royce was mostly known as a hardcore lyricist who, at times, delved into shock rap territory on songs with Eminem. But we were much more shocked when he showed up on this one-hit wonder's pop smash. Watch the video below for maximum effect.

19. Nelly f/ Tim McGraw "Over and Over" (2004)

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By 2004, Nelly was well established as a rapper who could switch hit as an R&B-type singer. Still, nobody expected the St. Louis spitter who gave us "Country Grammar" to scoop up country singer Tim McGraw for this slow jam. Even crazier? The song was a hit, making it to No. 3 on the Billboard Hot 100.

18. Eddie Murphy f/ Michael Jackson "Whatzupwitu" (1993)

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This is obviously a case of a friend calling in a big favor. Why else would The King of Pop get down on the woeful with a guy whose full-time hustle isn't music? Decades later, we're still wondering what was up with that. Murphy's OD tight wifebeater is all the awkward one video needs.

17. JYJ f/ Kanye West & Malik Yusef "Ayyy Girl" (2010)

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'Ye has ventured to the Far East before. His collab with the Teriyaki Boyz was exceedingly dope, but this one with K-pop group JYJ wasn't as tight. Maybe that's why Yeezy wasn't in the video.

16. Sugarland & Beyonce "Irreplaceable" (2007)

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The 2007 American Music Awards made this uncomfortable moment possible. Country effectively removes all of the soul from Beyonce's hit. Watch the performance in full below.

15. Bone Thugs-N-Harmony f/ Phil Collins "Home" (2002)

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Wow. Phil Collins has the least convincing head nod we've ever seen. And we know this video is supposed to be "deep", but PC blankly staring off into space had us laughing. Juxtapose that with four Ohio thugs draped in sports gear and you have one unintentionally awkward collaboration. Watch the video to see what we mean.

14. Big Pun f/ Incubus "Still Not a Player" (2000)

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When rock-rap was at its peak during the late '90s, Loud Records decided to capitalize and dropped a Loud Rocks compilation at the top of 2000. Letting Brandon Boyd anywhere near Pun's catalog was a mistake.

13. Rihanna f/ Chris Brown "Birthday Cake (Remix)" (2012)

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It's not that weird to see Rihanna and Chris Brown together now, but when her "Birthday Cake" remix dropped, it was borderline shocking, and certainly a bit uncomfortable. Hearing Breezy scream, "I wanna fuck you right now!" in the middle song will be jarring, no matter what history he has with the other singer.

12. Weezer f/ Lil Wayne "Can't Stop Partying" (2009)

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By the end of the Aughts, Weezer wasn't the same band we fell in love with in the '90s. The oddest decision of the latter part of their career has to be linking with Weezy for this awkward collab. Perhaps the similar spellings of Weezer and Weezy was too much to resist.

11. DMX f/ Marilyn Manson "The Omen" (1998)

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We know that DMX is a dark dude, so working with Marilyn Manson makes sense in theory, but they didn't mesh too well on this track. At least Manson didn't spit a verse, though.

10. Gucci Mane & V-Nasty "Let's Get Faded" (2012)

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For a moment, Gucci Mane and V-Nasty seemed like a great idea. Then it actually happened. This video serves as quick reminder for why BAYTL is better off forgotten. The 4,449 first-week units moved will also do that.

9. PSY f/ 2 Chainz & Tyga "Gangnam Style (Remix)" (2013)

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Why couldn't PSY be content with a billion YouTube views? Why did he have to get 2 Chainz and Tyga to rap over this track? At least there's no music video. No one's ready to see either of those guys do the gallop dance.

8. New Kids On The Block f/ Nice & Smooth "Dirty Dawg" (1993)

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This is what a desperate comeback looks like. NKOTB was well past their prime by the time this song debuted and its general lameness combined with corny raps from Nice & Smooth made sure they stayed there. After selling millions of records with prior releases, the Face The Music album that "Dirty Dawg" was featured on was a commercial failure. Shocker.

7. Jonas Brothers f/ Common "Don't Charge Me for the Crime" (2009)

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After releasing panned LP Universal Mind Control, Common really got on hip-hop's bad side by collaborating with the Jonas Brothers. He's redeemed himself since, but things were looking a little nervous for a moment there.

6. Taylor Swift f/ T-Pain "Thug Story" (2009)

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Taylor Swift and T-Pain's pre-taped performance of "Thug Story" at the 2009 CMT Awards was one of the most talked-about viral clips of that year, but we weren't really that impressed. It's not like we can't find the humor in T-Swizzle rapping about baking cookies, but the whole bit came across as more of a streetcchhhh than hilarious. Watch it below.

5. Korn f/ Nas "Play Me" (2003)

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Before Lil' Wayne was rocking with Korn in the video for "Prom Queen," Nas was collaborating with them and making really, really shitty songs. See? Doing something first isn't always a good thing.

4. Hilary Duff f/ Slim Thug "With Love (Remix)" (2007)

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Listening isn't necessary to realize how embarrassing this collab was for both parties. Slim Thug gained no pop appeal, and Duff gained no street cred. What a waste of time.

3. Sting f/ Twista "Stolen Car (Remix)" (2004)

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Diddy's award show duet with Sting was a classic moment in hip-hop history. Twista's music video with the same guy was just a classic fail. The '80s icon did look mighty comfortable with the groupies in the club scene though. Go 'head Sting!

2. Ja Rule, Swizz Beatz & Metallica "We Did It Again" (2003)

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Blame the Biker Boyz soundtrack for this travesty. No wonder this was the year Ja fell off. Metallica's collaboration with Lou Reed seems reasonable by comparison.

1. LFO f/ M.O.P. "Life Is Good" (2001)

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This is arguably the most bizarre collaboration ever, and we never even got to see the two groups being awkward together in a music video. Did the Mosh Out Posse like girls that wear Abercrombie & Fitch? Eh, probably not.

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