Prince the Rapper, an Absurdly Detailed Investigation

Prince is known as a musical great for many things—rapper isn't one of them.
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Prince Rogers Nelson is known as one of music’s greatest guitarists, singers, songwriters, producers, and performers. He never made it as a rapper. But it wasn’t for lack of trying.

Around the late '80s, Prince began to work rap into his music. The results were, to put it kindly, mixed. But it’s a part of his body of work that shouldn’t be ignored.

So here it is, an absurdly detailed investigation of Prince’s trials and tribulations as a rapper.

The '80s: Prince dabbles in rap before writing off an entire genre

Prince started rapping—kind of—in 1982 on tracks like “Irresistible Bitch” and “All the Critics Love U in New York,” but it wasn’t until 1987 that he got serious. “Housequake” from Sign O' the Times is unmistakably a rap song, with pitch-shifted vocals, no less. Was Prince blazing the path for Auto-Tune rappers? Well, not exactly.

The song that best sums up Prince’s then-opinion of a burgeoning rap scene is “Dead On It,” from the canceled but widely bootlegged TheBlack Album, which saw a promo release that same year (and an official release wouldn't come until 1994). The song is essentially a diss track aimed at every single rapper, like Kendrick’s verse on “Control,” only instead of singling anyone out by name, Prince tried to ether the very concept of rapping.

Choice lyrics include: “See the rapper's problem usually stems from being tone deaf / Pack the house then try to sing / There won't be no one left.”

Clearly, Prince was not thrilled with this whole newfangled rap thing. But since he famously did everything in his power to cancel the release of The Black Album, perhaps he knew that this anti-rap stance was ill-advised. Either way, Prince changed his tune a few years later, taking steps to learn the ropes of rap, and to become more self-consciously “hard.”

The Early '90s: Prince starts to take rap seriously and hires a full-time MC

Though he had dissed the entire genre just a few years earlier, Prince knew hip-hop was here to stay by the early '90s, and he knew he had to address it in order to stay relevant. His solution was to a) start frequently rapping himself and b) add a full-time MC to his band. Neither of these things went particularly well.

Anthony Mosley, known by most as Tony M., was an extra in Purple Rain, who hung around long enough to join Prince’s post-Revolution ensemble, The New Power Generation, as a backing dancer. At some point, Tony showcased his rapping skills for Prince, who must have thought, “Hell yes, this is just what my music needs.” Most fans disagreed.

Nobody wants a Tony M. comeback more than me, but the truth is, he just wasn’t good enough to be so heavily involved in Prince’s music. Prince was Prince. He needed to work with musicians on or near his level of artistry, like Sheila E. or The Time. Prince could have called Rakim, Run-D.M.C., Chuck D, or any prolific early '90s rapper if he wanted to take his music in a hip-hop direction. Instead, nearly half of the tracks on 1991's Diamonds and Pearls featured Tony M.

Here are a few standouts:

“Gett Off” was actually a big hit, thanks largely to an incredibly addictive flute riff. Neither Prince nor Tony rap more than a few bars each, but the Purple One still finds time to drop this clanger: “Lay your pretty body against a parking meter / Strip your dress down / Like I was strippin' a Peter Paul's Almond Joy.”

One of the endless B-sides from “Gett Off,” “Gangster Glam” features forgettable verses from Tony M. with Prince as the hook man. The record is more notable for its video, which sees Prince wearing what can only be described as a mankini.

On “Jughead,” a record that is universally derided as one of Prince’s worst, Tony attempts to describe a new dance known as, wait for it, “the jughead,” which I assume nobody ever actually tried.

One year later, Prince and the NPG released the unpronounceable Love Symbol album. Again, Tony M. had a part to play here, though he was far less prominent than on Diamonds and Pearls. Prince continued to develop his own rapping, but with mixed results.

One of Prince’s best forays into rap is “Sexy MF.” His bars are hilariously cheesy in the best way, but in all honesty, he sounded like a badass at the time. Tony M. doesn’t suit this beat as well as Prince, but his verse does lend some vocal variety to the song.

“The Flow” may be titled like a Seinfeld episode, but this is not Mixtape About Nothing material. Prince was better suited to ride a track with the smoothness of “Sexy MF,” but here his flow is too choppy. Tony also references “The Jughead,” which is unforgivable.

“Love 2 the 9’s” is a great soul song, that is, until Tony M. bursts in at the last minute like the Kool-Aid Man.

The entire Tony M. era of the New Power Generation saw Prince court rap fans with his style as well as his music. Tony M.’s dance group, The Game Boyz, brought street dancing to NPG stage shows, and Prince began to sing into a microphone shaped like a gun. (If you take this symbolism too literally, Prince was shooting himself in the face by trying his hand at rap.)

Tony M. only had three features on 1992’s Love Symbol, but that doesn’t mean Prince was starting to lose interest in his rapping services. In 1993, under the New Power Generation banner, Prince released one of the least known albums in his insane discography, with Tony M. providing lead vocals on almost every track. It was called—and I am not making this up—Goldnigga.

Goldnigga was credited solely to The New Power Generation, but it was Prince who produced all 16 tracks on the LP. Prince had been trying to become more “gangsta” for years, but Goldnigga was created all in good fun, a mixture of blaxploitation and of-the-times hip-hop. Unfortunately, it just wasn’t very good.

Recording an entire album as a lead artist should have given Tony M. the motivation to improve as an MC, but despite mixing up his flow and cadence on a handful of tracks, the results were mostly uninspired.

The album reaches its high point on track number seven, “Black M.F. in the House,” where Tony takes on the role of an incensed black patron being denied service by racist proprietors. The highlight, however, is Prince’s guest verse, delivered in the guise of a racist, white Southerner. It’s hilarious and satirical. At this point, it’s clear Prince realized that he could have fun with rap, and use it to spread an important anti-racist message.

Sadly, Prince decided to take a step back from rap after the release, going as far as to fire Tony M. from the band.

The Late '90s and Beyond: Prince waves goodbye to rap but stays in touch

Goldnigga was Prince getting rap out of his system—almost. He had one more full-on rap cut in him: the opening track on 1995's The Gold Experience, “P Control.” Prince’s flow is actually great; it’s like “Sexy MF,” but smoother. Dubious lyrics aside (the “P” stands for pussy), the song is a good listen if you don’t take it too seriously.

As the years went by, Prince would use rap the same way a drummer uses a cowbell: it was at his disposal but he didn’t feel the need to always employ it. In 1999, he finally worked with a professional rapper, Chuck D of Public Enemy. Then he featured on a Common track. Then Q-Tip featured on one of his tracks. But by this time, Prince was already years removed from rapping himself.

Despite Prince’s strange relationship with rap, it’s not surprising that he would become such a huge influence on so many of hip-hop’s biggest players. Prince’s otherworldly imagery was famously important to OutKast, and André 3000 in particular. Questlove is one of Prince’s biggest fans. Prince’s androgynous style and outlandish fashion sense have inspired swathes of rappers, particularly Young Thug. And finally, Prince’s willingness to challenge his record label has inspired countless rappers turned businessmen, most notably JAY-Z, to take control of their careers.

Prince may never have made it as a rapper but his mostly under-the-radar contributions to hip-hop have undeniably shaped careers and influenced sounds. Most importantly, though, we were blessed with these immortal lines: "From the heart of Minnesota / Here come the Purple Yoda."

For that alone, we should be thankful.

Editor's Note: In the interest of keeping things absurdly detailed, we also must mention "Pope," which was released in 1993 around the same time as Goldnigga—aka, the period Prince began to come into his own as a rapper. And it showed. I have no idea what "a loop is a loop is a loop" really means, but it sounds deep.

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