The Weirdest MC's Everyone Should Know About

The Weirdest MC's Everyone Should Know About

Published Mon, June 28, 2021 at 2:12 PM EDT

Tyler, The Creator's evolution has been something to behold.

He's one of the most outside-the-box creatives of his generation; able to shift from his early over-the-top scatological shock raps to much more introspective, personalized storytelling. He's traveled that course while carving a niche for himself as an artist that refuses to be boxed in, and he's maintained that ever-present uniquely off-kilter sense of humor that has endeared him to legions of fans. 

Tyler, The Creator is one of the latest in a long line of unapologetic rap weirdos; and here, the term "weirdo" is one of endearment. For a genre that has consistently been criticized for hyper-commercialization, Hip-Hop has a deep well of outside-the-box creatives. Those emcees and producers who have pushed their quirks to the forefront, and in doing so, helped blaze a trail for rap game oddballs. Whether or not you like the term "alternative Hip-Hop," there are definitely a school of artists who have pushed the genre to wonderfully strange and idiosyncratic places. 

From the moment De La Soul walked into that Hip-Hop 101 class in their video for "Me, Myself and I," there's been a need for rap nerds to be represented in the game. The early Native Tongues wore their quirkiness with pride, with songs about everything from talking fish to body odor to breakfast; acts like the Jungle Brothers, De La and A Tribe Called Quest wrapped their Afrocentricity in loveably oddball clothes. The Native Tongues collective did a lot to establish a space for left-leaning Hip-Hop artists in the music industry; but even De La and (especially) Tribe would tone down some of that early quirkiness as the 1990s progressed, trading in rap traditionalism for unapologetic whimsy. 

But the seeds had already been planted. 

Bay Area rap band Digital Underground dropped their debut album just as the Native Tongues were gaining steam; but D.U.. wasn't necessarily jazzy and explicitly Afrocentric; the Underground was a lot more party-friendly, but a penchant for wild costumes and funny alter egos, just as unapologetically weird.  In 1991, West Coast legend Del The Funky Homosapien dropped his debut album, I Wish My Brother George Was Here, a project that was about as left-field as Hip-Hop had seen from a West Coast artist, and the fact that Del was former N.W.A. member Ice Cube's cousin only added to the intrigue. 

Del's early singles focused on strange characters like Dr. Bombay and Mistadobalina, his raps were freewheeling and sometimes stream-of-conscious; and he was heavily marketed as the antithesis to the gangsta rap popular out of California in the early 1990s.

But one thing about rap distinctions; they can often be oversimplifications for a genre that crosses into a lot of styles. Del's songs could be just as dark and violent as the average gangsta rappers, but his persona was what was different; and that led to him approaching the subject matter from a different perspective. As opposed to braggadocios and confrontational, Del often seemed weary and resigned to reality of his surroundings. 

With West Coast artists like Del and Digital Underground repping for the quirky nerds of rap; New York City was still innovating with its own set of oddball creatives. Prince Paul helped invent the idea of rap nerdery with his work as producer of De La Soul's first three albums, and his own love of random pop culture, science fiction and comic books. Following his work with De La (and horrorcore act Gravediggaz), Paul launched his solo career and a seemingly-endless list of side projects with collaborators like Dan The Automator and Del. 

One of Paul's most notable projects is Handsome Boy Modeling School, his side project with Dan The Automator. Paul and Dan "star" as Chest Rockwell (Paul) and Nathaniel Merriweather (Dan); and they dropped their first album So...How's Your Girl? in 1999.


White People, the second album from Handsome Boy Modeling School, dropped in 2004, before Paul announced his split from Dan The Automater in 2006. 

If anyone could be considered the godfather of rap weirdness, it's Kool Keith. He made his debut with the Ultramagnetic MCs via a string of classic singles and 1988's masterwork Critical Beatdown. That album announced Keith as an emcee with his own distinct style of wordplay and a knack for strange, stream-of-consciousness references. After leaving the Ultramags, Keith moved to Los Angeles and moved into an apartment with DJ Kutmasta Kurt. It was there that the seeds were sown for Dr. Octagonecologyst, one of rap's strangest classic albums. 

The Dr. Octagon persona first appeared on the Ultramagnetic MC's demo "Smoking Dust," and after recording two tracks ("Technical Difficulties" and "Dr. Octagon") with Kutmasta Kurt, the bizarre wordplay and surrealist approach of Dr. Octagon came into full form as Dan the Automator came onboard to produce a full-fledged album.

The acclaim and notoriety that Keith gained from Dr. Octagon was something the iconoclast eventually rebelled against, refusing to be boxed in by his most famous alter-ego. So he crafted another one: Black Elvis. 

Black Elvis made his debut on Kool Keith's 1999 album Black Elvis/Lost In Space.

"It didn't really get where I predicted it to go; I was a Black rock star making Black music, but people didn't see a Black rock star," Keith told Pitchfork in 2012. "It was urban, but urban didn't know what it was because it was too new. I just naturally invaded into rock. All the magazines that covered rock and alternative covered me, but the urban magazines didn't understand it. They were too behind."

Artists like Prince Paul, Del The Funky Homosapien, Kool Keith and even the Beastie Boys have built names on following their own, stranger-than-most muse.

It's made Hip-Hop richer and broader; in the same way that you can point to Public Enemy's It Takes A Nation of Millions To Hold Us Back as a touchstone for political rap; or how you recognize the gangsta legacy of N.W.A.'s Straight Outta Compton; you can similarly point to the Jungle Brothers' Straight Out the Jungle as a pivotal landmark for "alternative Hip-Hop" or nerd rap, however you see fit to describe. 

Rap's weirdos have been around for more than 30 years. Tyler The Creator carries the banner for a younger generation that refuses to be stifled by any industry machinations or media stereotypes. Hip-Hop has been weird, fam. And we should all thank God for that. 



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