A History of Weirdo Rappers

Image via Complex Original

Debut: Late '70s

At a time when hip-hop culture arose as a middle ground between downtown art scene oddballs and uptown latchkey kids, luminaries like Queens rap and graf legend Rammellzee, as well as eventual Yo! MTV Raps host Fab 5 Freddy, helped bridge two worlds with a sudden shared interest. Rammellzee was a purveyor of a quietly influential rhyme style documented early on in a performance in Wild Style as well as “Beat Bop,” a collaboration with rapper K-Rob showcased in the classic graffiti doc Style Wars. Distinguishing him from his peers, many of whom were unusual in their own right, was his philosophy of gothic futurism, most succinctly explained as his own personal brand of theoretical linguistics, and his intricate style of dress, which quite often resembled samurai armor fashioned out of unassuming household objects.

Rammellzee was an eccentric, but he was a visionary; next time you hear a rapper floss about a Basquiat, remember that “Beat Bop” tapped a living Basquiat for its artwork 30 years prior.

Debut: 1985

From contributions to Ultramagnetic MCs' groundbreaking golden era classic Critical Beatdown through enduring work in the burgeoning late ‘90s hip-hop underground, Kool Keith's rep as an experimental hip-hop pioneer is indisputable. His mid-'90s concept album tear is the stuff of legend: Dr. Octagonecologyst, the story of a demented alien doctor who claims to be “half shark, half alligator, half man,” Sex Style, a lustful pimp rap odyssey, First Come, First Served, a foray into slaughterhouse horrorcore, Black Elvis/Lost in Space, an intergalactic robot’s struggle to find its way home, and many more.

Keith's skittering stream-of-consciousness flows perused rap's outer limits armed with exacting wit and laser-focused humor.

Debut: 1986

Biz Markie was the clown prince of Marley Marl’s seminal Juice Crew collective, a garrulous and whimsical rhymer with formidable beatboxing skills to match. Biz was a natural, kicking braggadocio and topical story rhymes (everyone sounds great with a little help from Big Daddy Kane), but he was never afraid to veer left into sillier territories, as he did on his 1988 debut Goin’ Off, which daringly opens with “Pickin’ Boogers,” an ode to the taste, texture, and excavation of snot. Biz’s absurdist streak manifested itself most memorably on 1989’s “Just a Friend,” a earnest cuffing season anthem until you get to the loud, purposefully off-pitch chorus and the music video, which floats off Biz’s outsized physical comedy, suiting him up as a b-boy Liberace.

Debut: 1988

Nowadays Pos, Dave, and Maseo are grizzled hip-hop legends, but when they arrived on the scene in the late '80s sporting asymmetrical haircuts, eye-catchingly weird threads and a “Daisy Age” message of peace and love, they were immediately pigeonholed as hippies. The psychedelic patchwork quilt of De La Soul and Prince Paul's first masterpiece 3 Feet High and Rising abetted the image with a playful, wide-eyed wonder and druggy, disjointed expansiveness, but the group was already bristling at their image on cuts like the single “Me, Myself and I” and its b-side “Ain’t Hip to Be Labeled a Hippie.” De La's harder edged sophomore album, poignantly titled De La Soul Is Dead, would arrive with dying daisies in a cracked, overturned pot for cover art.

They killed the colorful outfits and the flower child philosophizing, but never the restless spirit of adventure, left-of-center songwriting, and innovative production choices.

Debut: 1988

Shock G enjoys a twin legacy as both co-founder of the Oakland rap collective Digital Underground, known as much nowadays for their loopy g-funk classics Sex Packets and Sons of the P as for their introduction of a young 2pac to the hip-hop world, and as Humpty Hump, the charming prankster he became when he slapped on the old nose and glasses disguise to act out a little. Shock is a student of Parliament, and you can see the appreciation both in the airy funk of his production as well as his lyrics, which strike the same balance of sex-crazed glee and sci-fi madness.

Shock wasn’t your average g-funk guy. Just look at the concept for Sex Packets: a government invented orgasm pill intended for use during space travel gets into the wrong hands, and suddenly unsuspecting citizens are turned out. It doesn’t get much weirder than that.

Debut: 1989

The first time I ever heard solo Busta Rhymes music I was informed beforehand that the guy from Leaders of the New School had spent time in an insane asylum after the group broke up before coming out deranged and ready to take his career back. After one look at the fisheye lensed, padded-room freakout in the “Woo-Ha!! I Got You All in Check” video, I bought it without a peep. The asylum bit was bullshit, obviously, but Busta’s studious madness both on record (where he could adopt and co-opt quite literally any cadence he pleased) and in videos (watch literally any one of them. My favorite is “Gimme Some More.”) wasn’t. They set him apart from the more mannered tough guys that populated rap radio at the time. He made them step their game up.

Debut: 1989

Hate 'em or love 'em, Insane Clown Posse and their Psychopathic Records crew deserve their props here. Across over 20 years of devilishly lowbrow records, extensive tours, and more, Violent J and Shaggy 2 Dope pieced together a language and iconography, a whole counterculture, really, where misfits join in solidarity to celebrate their uniqueness. Beyond that they’ve made a few of the most absurd movies of all time (Look up Big Money Hustlas on YouTube, and thank me later), and they curate an annual festival that quietly touts one of the better rap lineups out there these days. Earlier this year, they sued the FBI for defamation in “Juggalo” jerseys and clown makeup. That’s six different kinds of unheard of.

Debut: 1989

Never mind the mask, the seclusion, and the time he sent impostors out to gigs, it’s MF Doom’s discography that illuminates how singular of a figure he is in the scope of modern rap. He’s got an album where he plays the three-headed dragon Godzilla fought. He made an album of wall-to-wall food jokes. He made another one full of guest verses from Adult Swim cartoon characters. Then there’s the more (comparatively) straight-laced classics Operation: Doomsday and Madvillainy, volleys of never-ending referential humor, oddly specific observations, and occasionally inscrutable word combinations. (“At the Stop-N-Go Mart acting like the spirit host done it”?), cascading walls of images washing over your mind like a TV flipping through stations, or better yet, pages turned in a comic book.

Debut: 1992

Ever since the early ‘90s the Atlanta mystics in the venerable Dungeon Family have put on for their city with a cerebral brand of soulful country-fried rap excellence. They were always a touch left of center, in their musical output (pick any of that camp’s breakthrough records, from Soul Food to Aquemini to East Point’s Greatest Hits for proof of the genius) and in the coolly eccentric way they carried themselves in public (see: anything Andre 3000 wore outside from 1996 to 2006, Sleepy Brown’s swanky pimp extravagance, or any of Cee-Lo’s Elton John inspired costumed endeavors… Better yet, really study the cover to their 2001 crew album Even in Darkness). The Dungeon Family blueprint set the stage for years of hip-hop mavericks to come, and it’s hard to imagine, say, a Kanye West having the freedom to do what he did without Three Stacks and company pushing the envelope years ahead of him.

Debut: 1993

Set aside your notions of Dirt within the context of the Wu-Tang Clan for a minute if you can, and really think about all the amazingly off-the-wall shit he managed to pull off in his career. He rapped like three different people at the same time. He sang with the unpolished conviction of a church deacon. He did public appearances totally shithoused and still killed. He collected a welfare check in a limousine. He rushed the Grammy stage when he didn’t win (10 years before Kanye’s award show incidents.) He dropped an album called Nigga Please (10 years before Nas backed out of a similar endeavor), where he rapped about hard drugs and the baby Jesus over comically expensive beats.

He damn near snuck into Roc-A-Fella in its prime. It still sucks to see him gone. He would’ve liked 2014. He would’ve had a god level Vine account.

Debut: 1995

Ever since they got their start rhyming about blowjobs and blunt guts in adolescence, Juicy J, DJ Paul, and the rotating cast of characters that fleshed out their Three 6 Mafia collective have written their own rules. They landed on a macabre serial killer shtick for their debut album, 1995’s seminal Mystic Stylez, only to tip closer to the mainstream on a series of albums that refined their sound and cleaned up their production without straying far from the reckless streak that colored their high school recordings. They’d go on to make the premiere lean anthem (“Sippin’ on Some Syrup”) and re-emerge with new relevance during Southern rap’s mid-2000s takeover.

They’re presently one of only two rap acts to ever win an Academy Award. Even today Juicy J enjoys continued celebrity as the rap game’s crazy Bombay Sapphire-swilling uncle, and Paul is still out chopping up bodies on records with his Three 6 all-star revue, Da Mafia Six.

Debut: 2000

Aesop Rock’s got a way with words, but we as listeners don’t always know what they all mean. As the man-at-arms in El-P’s ragtag Definitive Jux label and crew (and more recently, Slug of Atmosphere’s storied Rhymesayers imprint), Aes has cultivated a discography full of dark, dystopic songs fashioned out of thickets of imagery that don’t always come together in the deliberate, linear fashion the average rap fan expects of an MC. As he said on the Labor Days classic “Daylight,” “All I ever wanted was to pick apart the day, put the pieces back together my way.”

Debut: 2001

Anticon Records has always been a haven for hip-hop acts possessed of a vision too pure and unrestrained to concern itself with the machinations of the mainstream. From Why?, Sole, and Sage Francis on through Serengeti and Young Fathers the label has carved an identity out of refusing to be pinned down. A few different members of their ranks could’ve fit here, but Why?, Doseone, and Odd Nosdam’s first cLOUDDEAD project (though it technically didn’t come out on the label they all founded) typifies the fearlessly inventive subversion of hip-hop convention the Anticon army staked its reputation on, with its spectral beats, impressionistic lyrics, and off-kilter flows.

Debut: 2006

Where to begin with the legendary Based God? The affable, always-on internet presence? The ceaseless stream of mixtapes whose based vibes and ambient sounds have slowly trickled down into money-making mainstream records? The songs that make you wanna dance? The ones that make you wanna cry? The times he went after Joe Budden, Kevin Durant, David Banner, and Joey Bada$$? The night he popped out of the darkness to squash an A$AP Mob/Raider Klan beef, only to vanish without a trace like Batman? The devotional reverence of fans? The befuddled grumbles of naysayers? There are so many levels to Based World. Words don’t do it justice.

Debut: 2008

Das Racist got a raw deal. It was apparent to a few of us that what they represented was a witty but loving deconstruction of hip-hop culture and stardom spiced with added dashes of humor and social commentary. But for some reason the group drew a crowd that didn’t quite seem to grasp their depth, that treasured the silliness of the songs but not their fire about being brown in post-9/11 America, and a perplexing indifference from hip-hop audiences perturbed because they couldn’t sniff out the motives. It’s unfortunate. While the union lasted, the trio of Heems, Dapwell, and Kool A.D. crafted a vibrant mutation of New York rap that straddled genre lines, touching on dance music and indie rock without reaching or pandering.

Debut: 2009

In not much more than five years Odd Future has parlayed a youthful taste for the macabre into international stardom, starting out with a string of mixtapes that crossed an admiration for Slim Shady at his most deranged with the quirky, adventurous production of prime Neptunes and ended up with Billboard chart successes and a TV show in the process. Camp Flog Gnaw, their annual Los Angeles festival/carnival, has seen performances by everyone from Kanye West to Flying Lotus. Tyler, the Creator, Earl Sweatshirt, Frank Ocean, and the rich array of friends and affiliates in and around the OF enterprise took the rap game by siege largely as a self-contained unit, too, free from the feature-hungry glad-handing that homogenizes too much of rap’s mainstream.

They work with who they want on what they want, and there aren’t many charting rap entities out there for whom the same could be said of in 2014.

Debut: 2009

The enigmatic butterscotch boss is unpredictable. He might pull up with Mulan in a candy painted swan, or he might be in Ralph Lauren, promethazine steady pouring. RiFF RAFF’s boasts sound like a kid trying to describe scenes from a cartoon he’s watching in real time, and his clothes are brighter than '90s Nickelodeon game show set designs. They don’t call him the Neon Icon for nothing. RiFF is weird enough to throw traditional rap fans for a loop without very much effort, but he’s also very, very Texas, one of the few rap acts able to boast work with a casually rangy list of collaborators from Chief Keef to Action Bronson to Paul Wall and Slim Thug to Diplo. James Franco played a version of him in a movie. James Franco!

Debut: 2011

Young Thug pisses off a lot of rap fans, and you get the sense he could care less. His diction perplexes all but the most attentive listeners at one point or another in a song, and his personal style and slang have tripped off a host of lunkheads to lob homophobic slurs at a guy who isn’t even gay. Thugger has touched a number of the hottest records of the year (“Danny Glover,” “Stoner,” “About the Money,” “Lifestyle,” “Old English,” etc.), and it doesn’t matter what he looks like doing it. He paints his nails and wears a gaggle of pink, and condolences if that’s a problem for you. He’s doing more audacious things with words than half his peers and in better clothes, too. Deal.