Mike Tyson’s Top Ten Rap Cameos

Reggie Rock Bythewood’s One Night in Vegas, airing on ESPN tonight as part of the network’s “30 for 30” documentary series, shines a light on the little known friendship and many parallels between tortured souls Mike Tyson and Tupac Shakur. The title of Bythewood’s documentary is a reference to Sept. 7, 1996, when Shakur was fatally wounded on the Las Vegas Strip after taking in what would be Tyson’s last successful title defense, against Bruce Seldon. ‘Pac, who’d recorded music specifically for Tyson to use during his entrance that night (something he’d done previously for Tyson’s rematch against Frank Bruno earlier that year), wasn’t the only rapper to take inspiration from the champ. The most feared and virile black athlete of his day, Tyson’s name has been an ubiquitous lyrical reference point for more than 20 years (see ’99’s Ego Trip’s Book of Rap Lists for a rundown of classic Tyson-centric one-liners), and the subject of more than a few full-on tributes. The respect was mutual: a longtime rap fan, Mike was a regular presence at NYC nightspots like the Latin Quarter during rap’s golden era, hobnobbing with the likes of Eric B. and Rakim and LL Cool J, and turning up in numerous videos over the years. Here’s a look at some of his more notable cameos, both literal and in spirit, in chronological order of appearance.

Spoonie Gee, “Mighty Mike Tyson” (1987)

The pioneering Harlem MC (of “Love Rap” fame) was probably the first rapper to pay tribute to the then-rising star, on this Marley Marl-produced track from his ’87 comeback LP, The Godfather of Rap.

DJ Jazzy Jeff and the Fresh Prince, “I Think I Can Beat Mike Tyson” (1989)

The lead single from Jeff and Will’s lackluster third LP, …And In This Corner, is probably the best-known lyrical testament to Tyson-induced fear. With its Don King and Alfonso Ribeiro cameos, and the pricless victory dance Iron Mike does after KOing the future box-office king, the video is as entertaining today as it was back then.

Breeze, “T.Y.S.O.N” (1989)

Dubbing himself “The young son of no one,” L.A. rapper Breeze (not to be confused with Philly’s MC Breeze) named his first and only LP T.Y.S.O.N.. The title track, which attempts to make a case for the comparison with lines like “Ain’t nobody hitting like Tyson/I’m going the length/I’m the young son of no one in rap/Like the man I mentioned two lines back,” confusingly samples lines from Muhammad Ali, not Mike.

Ice-T, “New Jack Hustler (Nino’s Theme)” (1991)

Probably the earliest example of what you might call the “Mike-as-street-cred-accessory” genre, the clip for Ice’s contribution to the New Jack City soundtrack finds Mike chatting on a bulky carphone and politicking with members of the Rhyme Syndicate.

2Pac, “Road to Glory” and “Let’s Get It On” (1996)

Considering the mountain of bastardized, unfinished 2Pac recordings that continue to emerge year after year, it’s somewhat shocking that studio versions of these tracks, recorded as entrance music for Tyson’s fights with Frank Bruno (“Put your hands up, Mr. Bruno/Why? Cause Mike Tyson about to violate that ass tonight”) and Bruce Seldon, have never turned up. Currently, the only way to hear them is through the prohibitive din of the audio from the actual fight broadcasts. Not to be confused with the “Let’s Get It On” 2Pac recorded years earlier with Biggie (as well as Heavy D and Grand Puba), this one was apparently recorded in 20 minutes just days before the Seldon fight, as producer Robert Gutierrez explains in One Night in Vegas. A clear, studio recording played in the film reveals an eerie reference to Club 662, site of the afterparty ‘Pac was en route to when he was gunned down on the Strip.

Fraze, “Ruff Ride” (1997)

Well-established artists weren’t the only ones to benefit from the substantial weight of a Tyson cameo. Filming was already in progress on shooting the Miami Beach-set video for this little-known 69 Boyz-produced single by South Florida rapper Fraze when Mike, who appeared in the video gratis (2 Live Crew’s Fresh Kid Ice, Fraze’s manager at the time, is a Tyson friend), just happened to roll by in his Lamborghini. (Disclosure: my fiance’s brother, Wayne Williams, worked with Fraze and appears in the video.)

Eric B. appears with Mike Tyson on “Monday Night Raw” (1998)

Rakim’s former DJ is said to have overseen Tyson’s security detail in the years following his split with the God MC in the mid ’90s. One thing’s certain: the former presidential nominee was in the ring with Mike when he tussled with Stone Cold Steve Austin during a brief foray into the WWE.

Canibus, “Second Round K.O.” (1998)

It’s hard to believe now but Canibus’s (and Wyclef’s) battle with LL Cool J was one of the biggest, if not the biggest, rap feuds of its day. These days, Canibus is probably remembered just as well for the memorable pep talk Mike gave him (“Your main objective out here is to do nothing but eat, eat, eat ,eat MCs for lunch, breakfast…”) — and the now-comical video where the champ coaches him through all sorts of training stuff (sweating out pushups, running on the beach) — as for his impressive lyrical dexterity.

Diddy, “Bad Boy 4 Life” (2001)

It’s easy to miss Mike’s appearance in this cameo-heavy (Ben Stiller, Shaq, Ice Cube, Dave Navarro, Pat O’Brien) video for Diddy’s post-Club New York incident comeback, but freeze your video player at 3:48 to catch the ex-champ riding by on a multi-hued motorcycle.

Nas, “Legendary (Mike Tyson)” (2008)

Like ‘Pac (in 2003’s remarkably coherent Tupac: Resurrection), Tyson has already been contextualized in a much more insightful documentary than One Night in Vegas: James Toback’s Tyson. Nas, whose longtime associate Salaam Remi scored the film, contributed this song (previously released to mixtapes) to the closing credits, employing a bullet-point approach similar to his 2004 God-MC tribute “U.B.R. (Unauthorized Biography of Rakim).”

Bonus: Lil Wayne “Mike Tyson Flow” (2008)

Sometimes identified as “American Dream” and tagged “featuring Mike Tyson,” this mixtape track (which originally appeared on 2008’s Louisianimal), begins with a grab of Mike’s infamous “I’m the best ever” rant.