The 25 Strangest Rapper & Non-Rapper Collaborations

kanye katy perry

Hip-hop has worked its way to becoming arguably the most popular form of music in America, especially among young people. From President Obama to Miley Cyrus, everyone seems to listen to rap. As hip-hop has matured, plenty of artists within the culture have shown appreciation for other forms of music. Sometimes, mutual respect from both sides merge and birth musical collaborations that bend genres. Here, XXL looks at 25 of the strangest collaborations by rappers with non-rap artists. Rock on! —XXL Staff


Justin Bieber ft. Kanye West & Raekwon “Runaway Love (Remix)” (2010)
Why It Was Strange: Well, for starters, Justin Bieber was two-years-old when Raekwon's Only Built 4 Cuban Linx... came out.


Bone Thugs-N-Harmony ft. Phil Collins “Home,” Thug World Order (2002)
Why It Was Strange: The song itself, which sampled singer Phil Collins and featured him on the hook, turned out pretty dope, actually. But the video, where the British crooner was uncomfortably grilling the camera? Yeah, that was awkward.


DMX ft. Marilyn Manson “The Omen,” Flesh of My Flesh, Blood of My Blood (1998)
Why It Was Strange: Both artists were known for being dark men (it was also one of X's nicknames), but their collaboration still made for an unexpected pairing. To say Manson sounded creepy on this cut would be an understatement.


Limp Bizkit ft. Method Man “N 2 Gether Now,” Significant Other (1999)
Why It Was Strange: Meth, as part of Wu-Tang, was part of one of the most legendary groups in hip-hop. Meanwhile, Limp Bizkit, though popular, was a curious rock-hop band without much credibility in rock and hip-hop. DJ Premier adding his touch with an ill instrumental didn't make it any less strange.


Nelly ft. Tim McGraw “Over and Over,”Suit, (2004)
Why It Was Strange: Wonder if the guy who was riding down the block with a streetsweeper ready to go, spitting that country grammar, thought he'd be singing (yes, singing) on a track with a county sensation? Maybe.


New Kids on the Block ft. Nice & Smooth “Dirty Dawg” (1994)
Why It Was Strange: Something was a little off about the boy band that sang “Step By Step” and the golden age hip-hop duo that crafted cuts like “Sometimes I Rhyme Slow” sharing a track.

eminem elton john

Eminem ft. Elton John “Stan” (2001)
Why It Was Strange: This performance went down at the Grammys where Eminem was nominated for Album of the Year for The Marshall Mathers LP. GLAAD protested Em's nomination in Los Angeles, accusing the rapper of being homophobic. As a response, the Detroit native teamed with the openly gay Elton John for a literal and figurative “fuck you.”


LL Cool J & Elmo “Addition Expedition” (2008)
Why It Was Strange: The “Mama Said Knock You Out” rapper and that red furry guy. Dream team.

jay-z linkin park

Jay-Z and Linkin Park “Numb/Encore,” Collision Course (2004)
Why It Was Strange: These two put out an entire album together. But Jiggaman is one of the greatest of all-time, and Linkin Park is a bizarre rap/metal hybrid. It was also strange that the song came out so well.


Michael Jackson ft. The Notorious B.I.G. “This Time Around,” History: Past, Present and Future, Book 1 (1995)
Why It Was Strange: It was rare for Michael Jackson to collaborate with rappers, but when he did, why Biggie?

beach boys

Fat Boys ft. Beach Boys “Wipeout” (1987)
Why It Was Strange: Sure, this charted pretty high on Billboard, and both of these groups have the word “Boys” in their name. But other than that? Hmm. Strange!


LFO ft. M.O.P. “Life Is Good,” Life Is Good (2001)
Why It Was Strange: LFO was one of the softest boy bands around (that's saying something), and M.O.P. are the Brownsville, Brooklyn-bred Mash Out Posse—one of the hardest rap groups ever. Come on, son!


Jay-Z ft. Lenny Kravitz “Guns and Roses,” The Blueprint 2: The Gift and the Curse (2002)
Why It Was Strange: Jay-Z and Lenny Kravitz teaming up over an Heavy D track could have been incredible. It simply wasn't.


Wale ft. Lady Gaga “Chillin,” Attention Deficit (2009)

Why It Was Strange: The Interscope connection made sense. A label trying to give a new rap artist a pop hit made sense. Nothing about this felt organic, though. For what it's worth, these two collaborating would probably be stranger now than it was then.


Katy Perry ft. Kanye West “E.T.” (2010)
Why It Was Strange: Just because this song was popular (147 million hits on YouTube, and counting), doesn't make it alright.


Wyclef Jean ft. The Rock “It Doesn’t Matter,” The Ecleftic: 2 Sides II a Book (2000)

Why It Was Strange: The Rock was a pretty good football player. He's had a great wrestling career. His acting, well, it happened. But getting on wax? With Wyclef? It doesn't matter.

john cena

John Cena ft. Bumpy Knuckles “Flow Easy,” You Can’t See Me (WWE) (2005)
Why It Was Strange: John Cena and Bumpy Knuckles (also known as Freddie Foxxx) are both tough guys, but this track was tough on the ears.

paris hilton

Paris Hilton ft. Fat Joe & Jadakiss “Fightin’ Over Me,” Paris, 2006

Why It Was Strange: Paris Hilton is strange. Paris Hilton singing is strange. Paris Hilton working with rappers is strange. Paris Hilton working with two street savvy New York rappers is face-melting.

lil wayne

Enrique Iglesias ft. Lil Wayne “Push,"Insomniac, 2008

Why It Was Strange: Lil Wayne was near the pinnacle of his Internet-flooding, recording-frenzied pre-Tha Carter III run when he hopped on this one. Maybe he realized something was a little off, as he didn't appear in the official video.

willie nelson

Snoop Dogg ft. Willie Nelson “My Medicine” (2008)
Why It Was Strange: This makes sense because Snoop and Willie are both weed aficionados, and that's what this song is about. But who would have thought a near 80-year-old Texan and the Long Beach-bred Doggfather would actually get on wax together?


Puff Daddy ft. Jimmy Page “Come With Me,” Godzilla: The Album (1998)

Why It Was Strange: Diddy was mounting his mainstream takeover in the late 1990s, and this collaboration with the revered British guitarist Jimmy Page certainly didn't hurt. Puff was rock-rapping here, but still found a way to bop in the video.

clipse justin timberlake

Justin Timberlake ft. Clipse “Like I Love You,” Justified (2002)

Why It Was Strange:Since their early career success, the Thornton brothers have been known for their coke rap. JT has respect from plenty of artists in hip-hop now, when the song dropped a decade ago, he was fresh off of being the frontman of one of the most popular boy bands in history.


Busta Rhymes ft. Ozzy Osbourne “This Means War!!,” Extinction Level Event: The Final World Front (1998)

Why It Was Strange:Throughout his career, Busta has been an eccentric talent. But his collaboration with Ozzy was truly out of left field.

krs one

R.E.M. ft. KRS-One “Radio Song,” Out of Time (1991)

Why It Was Strange:It's not unbelievable that the teacher himself, KRS-One, would make a song about his issues with the radio. Why he did it with successful rock band R.E.M. is another story.