A History of Rappers Performing on WWE
Wiz Khalifa wasn't the only rapper to grace the squared circle.
Image via Complex Original
Last week on Monday Night Raw, Wiz Khalifa—apparently blazed out of his mind—showed up as the musical guest for the evening. It’s not entirely unprecedented—after all, Khalifa collaborated with John Cena on the soundtrack to WWE 2K15—but it was certainly an odd, awkward sight. There was that dodgy musical performance to the tragically white crowd. There was that Mizdow freestyle sketch backstage. And, of course, there was that really awkward handshake between Khalifa and Vince McMahon. Vince seemed nervous, like a freed animal that’s looking to bolt at the first window of opportunity.
The WWE rarely collaborates with rappers, unless you count the numerous rapper gimmicks over the years. But, really, they ought to collaborate more, because the few rapper guest spots have been reliable crowd pleasers. Here, for your viewing and listening pleasure, is a History of Rappers Performing on WWE. Let’s break it down.
Wrestlemania Rap
Rapper: Run-DMC
Event: Wrestlemania V
City: Atlantic City
Date: 1989
Wrestlemania V’s card was loaded down with iconic names. The Rockers. Mr. Perfect. Jake the Snake. Andre the Giant. And, of course, the Main Event showdown between the Hulkster and the Macho Man. But, despite all this starpower, the show lacked the grandeur that Wrestlemania is associated with — two matches ended via DQ, and nearly all of the matches ended in under 10 minutes.
Still, we’ll always have the Run-DMC performance of “Wrestlemania Rap,” which they wrote specifically for the event. The trio were riding high on their cover of “Walk This Way,” and it makes sense that they would cross over again, by introducing rap onto the grandest stage of them all.
Makes Me Wanna Shoop
Rapper: Salt-N-Pepa
Event: Wrestlemania XI
City: Hartford
Date: 1995
Salt-N-Pepa exuded sex. I still remember the promos, where the ladies made eyes at the camera, pursed their kissy lips, and purred that they were going to “add some Salt-and-Pepa” to Wrestlemania XI. Between them, Pamela Anderson, and Jenny McCarthy, Wrestlemania XI had us sweating. Prior to the main event between Lawrence Taylor(??) and Bam Bam Bigelow, Salt-N-Pepa performed “Whatta Man.” And as far as we’re concerned, the PPV ended right there. We’ve blocked out the rest of it, and for good reason.
Woo Hah!!
Rapper: Busta Rhymes
Event: Smackdown!
City: Atlantic City
Date: 2002
Coming at the tail end of the Attitude Era, this guest appearance is a classic moment. It features The Rock and Busta Rhymes, singing a perfect, hilarious duet of The Drifters’ “Under The Boardwalk.” What really makes this clip is how damn happy Busta looks. He’s laughing and marking out the entire time. Obviously, the guy’s a fan, probably since childhood, and he’s savoring every moment on the mic.
It's the D-O-DOUBLE-G!
Rapper: Snoop Dogg
Event: Monday Night Raw
City: Jacksonville
Date: 2009
When it comes to guest spots, the WWE usually tries to play it safe. It’s difficult to imagine that they would have invited Snoop years ago—1993 Snoop is a hell of a lot different than 2009 Snoop. But still, the Doggfather is one of the only people on this list who actually got physical in the ring. Snoop rushes out to save Hornswoggle from Chavo Guerrero, and he handles himself convincingly, for a guy who’s never laced up a pair of boots. Snoop delivers a hard clothesline followed by a spear/spinebuster, and Chavo, fake gangster that he is, is down for the count.
You Know What Time It Is...
Rapper: Flavor Flav
Event: Monday Night Raw
City: Pittsburgh
Date: 2010
The greatest sideman to ever do it had a career revival in the mid-'00s, when he became the breakout star on a slew of VH1 reality TV shows. First, there was The Surreal Life. Then, there was Strange Love, where he struck up a romance with Ivan Drago’s wife. Then, there were two seasons of Flavor of Love which were both funny and depressing as hell (remember when that girl took a shit on the floor?).
On this Monday Night Raw guest spot, Flav gets into the ring and gets the crowd hyped. But our favorite bit has to be this backstage segment, where William Regal tries to rap, and Flav gives him the smackdown he deserves. Yeaaahh Boooyyyy!!
Happy Birthday, Rock!
Rapper: Pitbull
Event: Monday Night Raw
City: Miami
Date: 2011
You know you’re a big deal when the WWE dedicates an entire show to your birthday. The Rock was celebrating 39 years of jabroni-beating and pie-eating in his hometown of Miami, Florida, when native son Pitbull came out to amp up the festivities. But of course, it wasn’t just him. Flanking Pitbull was the Miami Heat Dance Team, and if anyone knows how to work their hips, it’s Miami girls. Sounds like a party to us.
Iron Mike Flash Mob
Rapper: Timbaland
Event: Wrestlemania XXVIII Axxess
City: Miami
Date: 2012
There’s something about Miami that brings out the best in the WWE, and this Timbaland bit is no exception. Layla and Eve surprised the multi-talented producer with a flash mob performance, but Timbaland is secondary to the whole spectacle. It’s actually "Iron" Mike Tyson who manages to steal the show. There’s something both hilarious and terrifying about seeing the baddest man on the planet get down, and we’re all probably lucky that the song ended when it did.
Are You a Wild One?
Rapper: Flo Rida
Event: Wrestlemania XXVIII
City: Miami
Date: 2012
This was the first Wrestlemania rap performance in years (Limp Bizkit doesn’t count, and Kid Rock barely counts). There’s not much to be said about this, other than to appreciate the grandeur and the spectacle of the whole thing. The fireworks. The massive sets. We’ve heard of arena rock, but this is arena rap, at its very finest.
NCIS Is Looking for Recruits
Rapper: LL Cool J
Event: Monday Night Raw
City: Memphis
Date: 2014
This guest spot is sort of strange. When you get the GOAT to appear on your show, shouldn’t you feature him in the center of the ring? But instead, Renee Young interviews him and Chris O’Donnell at ringside, where they promote NCIS and proclaim their love for the Bella Twins (who doesn’t love Twin Magic?). Hopefully, the WWE can bring LL Cool J back as a guest host sometime (hosting is all he seems to do these days anyway!), and give him something more substantial to partake in.
Honorable Mention: Shaq-Fu
Rapper: Shaquille O’Neal
Event: Monday Night Raw
City: Washington, D.C.
Date: 2009
Yeah, okay. Maybe we’re stretching the "rapper" label a bit thin, but it counts, dammit. And whenever we get the chance to highlight a celebrity cameo this awesome, we’re going to take it. This may be one of the only times in his life that The Big Show has to look up to someone, and that, by itself, makes this bit exciting. You find yourself thinking of two giant monsters, like Godzilla and Ghidorah, trampling a city together under their size 22’s.