8 of the Most Unexpected Collabs in Music History

Did they work to perfection or fail miserably?

Collaboration is at the heart of the music industry. Whether forced by music executives and managers or authentically driven by mutual respect, music collaboration allows artists to share ideas, tap into different skills, and expand their reach. Over the course of music history, we’ve seen plenty of mind-blowing collabs that we didn’t know we needed. In contrast, we’ve also suffered through mind-numbing collabs we desperately wish to forget. In no particular order, here are some of the more unexpected collaborations in music history. 

Top 50 Rap Albums of the Decade

Jay-Z & Linkin Park – Collision Course

Originally put together for an MTV show, HOV teamed up with one of the world’s biggest rock bands on the Grammy-winning EP, Collision Course. The six-track project featured mashups of songs from each artist, most notably with “Numb/Encore.” Both Jay-Z and Linkin Park were very open about the mutual respect they had for one another. That’s a huge reason why this rock/rap crossover worked to near-perfection.

Mariah Carey & Ol’ Dirty Bastard – “Fantasy (Remix)”

It’s hard to picture the de facto Queen of Christmas Music linking with someone as brash and gritty as Wu Tang’s Ol’ Dirty Bastard. The two worlds collided on the remix to Carey’s hit single “Fantasy” in 1995.  However, something about this streets-meets-chic collab just doesn’t feel right. This one left me thankful that the “hey let’s get a rapper on this random pop song” strategy is far less popular nowadays than it was twenty years ago. 

Tyler, The Creator’s Best Two-Part Songs, Ranked

Run DMC & Aerosmith – “Walk This Way”

Attempting to bridge hip-hop’s first mainstream superstars with seemingly past-their-prime rock legends is an interesting idea. What’s the worst that could happen? Initially, neither group was excited about this collaboration, with each apathetically scoffing at the other. The brainchild of legendary producer Rick Rubin took Aerosmith’s 1975 megahit and repurposed it a decade later through the lens of Run-DMC. The remixed song was a smash hit. “Walk This Way” launched Run-DMC into stadiums that hip-hop acts had previously never been invited to. Additionally, the track injected new life into Aerosmith’s career that led to multiple hits in the 90s. 

Ozzy Osbourne & Jessica Simpson – “Winter Wonderland”

At the turn of the century, Jessica Simpson was the golden child of pop music in white America. The former childhood choir singer and near-Mickey Mouse Club member embraced an “anti-sex appeal” image to contrast Britney Spears and Christina Aguilera. A collaboration with Black Sabbath frontman Ozzy Osbourne, aka the Prince of Darkness, was the last thing anyone expected – on a Christmas song nonetheless! “Winter Wonderland” has been covered over 200 times, and this rendition will leave you wishing it wasn’t.

God Bless The Trap

Kanye West & Paul McCartney – “Only One,” “FourFiveSeconds,” & “All Day”

The 2010s saw a rollercoaster of highs and lows surrounding Kanye West. His work with Beatles legend Paul McCartney was most definitely a high.  Collaborating on three tracks in 2014 and 2015, West and McCartney meshed extremely well as one of the more unexpected collaborative duos. Most notably, many of West’s younger fans proclaimed on social media that this McCartney guy was set to have a huge career thanks to the Kanye cosign.

Justin Bieber & Busta Rhymes – “Drummer Boy”

Coming off his mega-hit debut album My World, teenage heartthrob Justin Bieber attempted to write the next classic Christmas album with his Under the Mistletoe project. The Drumline-type breakdown coupled with Busta’s gruff style and ferocious bars harshly counter Bieber’s pre-pubescent melodies. This is one of the more anticlimactic and downright cringe-worthy collaborations in recent memory.

Kids See Ghosts – KIDS SEE GHOSTS, Album Review

Snoop Dogg & Banda MS – “Qué Maldición”

It’s no secret that Los Angeles native Snoop Dogg loves banda music. In April of 2020, his dream of creating his own banda song was realized in the form of “Qué Maldición.” The track fuses Snoop’s signature brand of G-funk hip-hop with the swinging brass sections of Mazatlan-based group Banda MS. Snoop delivers his verse in Spanglish, creating a cross-cultural mashup perfect for a top-down ride through the streets of LA.

Jonas Brothers & Common – “Don’t Charge Me for the Crime”

Rounding out the list, we’ve got another regrettable teen-idol meets legitimate rapper collab. With this track, however, Common doesn’t just drop a verse and cash a check. He shows up at several points in the song, offering various quick one-liners and ad-libs. What makes this song truly unforgettable is the narrative. The track tells a story about Common and the Jonas Brothers teaming up to commit a bank robbery. The real robbery here is that we never got a music video for this unexpected collab and all its cringeworthy glory.

We hope you enjoyed this list compiling the eight most unexpected collabs in music history. Click any of the above song titles to hear the tracks in their entirety. Lastly, for more editorials, 9 of the Most Unbreakable Records in Sports History.

My Cart Close (×)

Your cart is empty
Browse Shop