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Dr. Octagon and the Surgical Perverseness of Kool Keith

Twenty-five years ago, the Ultramagnetic MCs rapper teamed up with Dan the Automator for a stone-cold classic and one of the wildest excursions in hip-hop history

Richard A Chance

No year in hip-hop history sticks out quite like 1996: It marked the height of the East Coast–West Coast feud, the debut of several artists who would rule the next few decades, and the last moment before battle lines between “mainstream” and “underground” were fully drawn. The 1996 Rap Yearbook, a recurring series from The Ringer, will explore the landmark releases and moments from a quarter-century ago that redefined how we think of the genre. Today, we’re looking back on Kool Keith’s first post–Ultramagnetic MCs record, his otherworldly team-up with Dan the Automator under the name Dr. Octagon, Dr. Octagonecologyst.


Though it feels like 8,000 or so, Kool Keith raps the word rectum only eight times over the course of Dr. Octagonecologyst, the mesmerizingly perverse underground hip-hop classic credited to Dr. Octagon (the most famous of the deified New York City rapper’s 50-odd aliases) and first released on May 7, 1996. Yes, on Friday, this eternally astounding record, in all its porno-surrealist glory, will be old enough to rent a car. Do not rent a car to Dr. Octagonecologyst, however, lest the good doctor perform any of his specialties (which per the album include “intestine surgery, rectal rebuilding, relocated saliva glands, and chimpanzee acne—and of course, moosebumps”) in the rental car’s back seat, thereby forfeiting the security deposit. (This is the same skit that lists Dr. Octagon’s office line as “1-800-PP5-1-Doodoo”; I have been old enough to rent a car for nearly 20 years, and each time I hear that phone number it’s still the funniest shit I’ve ever heard in my life.)

OK, so that one time, he says rectal, not rectum, and he’s not rapping there, technically; same deal on another skit when he gravely intones, “You have ptomaine poisoning on your tongue. Say Ahh. You have bees flying around your rectum.” Still, though: (only) eight instances of (usually) the word rectum (mostly) rapped across 20 tracks on the album’s canonical 1997 rerelease. “You beat it like Michael Jackson in my atmosphere / Gerbils for rectums, I break you off like Richard Gere,” raps Dr. Octagon. “I do much work on heavy stomachs like Levert / Put up some money, I bet my tools’ll make your rectum hurt,” raps Dr. Octagon. I don’t mean to fixate on this, but we all have our fixations when it comes to Dr. Octagonecologyst, which stands among the most beloved and dissected and perhaps misunderstood rap records of its era, an X-rated sci-fi odyssey of dazzling prurience and lurid imagination, and a solo debut so vivid and monolithic that Keith has spent the past quarter-century firing off 30-odd subsequent albums and concocting 50-odd other aliases lest you pigeonhole him solely as the “Oh, shit, there’s a horse in the hospital” guy. (That’s my favorite skit.)

And so we come here today to praise Dr. Octagonecologyst while also freeing Kool Keith from the monumental burden of being Dr. Octagon all the time. In the mid-’90s, the beyond-eccentric rapper—born Keith Matthew Thornton in the Bronx in 1963—was best known for his stint in the Golden Age crew Ultramagnetic MCs, whose 1988 debut, Critical Beatdown, is an all-timer (“Kool Keith Housing Things” is truth in song-titling) and whose full catalog deserves more respect than it gets. (“Light up your inner skull and burn up your rectum,” Keith boasts on a late-period throwaway called “Talkin’ Out Ya Ass,” which flaunts more raw personality than plenty of his opposition’s failed hit singles. “MCs are doo-doo, I never did respect ‘em.”) But this guy was destined for different planets, different galaxies, different schools of musical and medical and sexual thought. And with some help from San Francisco producer Dan the Automator, whose taste for eerie whimsy would soon light up records by the likes of Gorillaz and Handsome Boy Modeling School, Keith kicked off one of the wildest solo careers in rap history by reinventing himself as a sex-crazed, homicidal, space-age experimental surgeon named, yes, Dr. Octagon. So many rectums to burn up, so little time.

If Dr. Octagonecologyst—bolstered by extra production from longtime Keith cohort KutMasta Kurt and dizzying scratching from turntablist DJ Qbert—has anything resembling a breakout single, it’s “Blue Flowers,” a hypnotic 23rd-century earworm less memorable for anything Keith says (“Cybernetic microscopes and metal antidotes / Two telescopes that magnify size of a roach”) than for the absurdist swagger with which he says it. Kool Keith, anywhere and under any alias, doesn’t have to stay on beat if he doesn’t want to. His rhymes don’t have to rhyme if he doesn’t want them to. He doesn’t have to make one iota of goddamn sense if he doesn’t want to. He can turn nonsense declarations like “Half-shark-alligator, half-man!” or “Earth people, New York to California! / Earth people, I was born on Jupiter!” into infectious choruses. He can follow up a deviant sex jam called “Girl Let Me Touch You” with an even more aberrant barrage of goofy threats called “I’m Destructive.” (“Bash in your head with 10 full cans of Campbell’s soup / I’m on the roof and I let the pigeons out the chicken coop.”) This is a stupendously baffling record, a Neptunian porno mag that doubles as a Dadaist B-movie script, an outré masterpiece that threatened to turn Keith himself into a mainstream star.


But outright acceptance, even within ostensibly flamboyant underground-rap circles, was never Keith’s goal; he has never stood still long enough, physically or stylistically, to risk mass culture’s stultifying embrace. Dr. Octagonecologyst landed him a coveted slot on the 1997 Lollapalooza tour, but he never showed, as noted in an admiring if unsettled 2001 New York Times piece that hailed him as “part George Clinton, part Marquis de Sade.” By 2001, of course, Keith had already put out approximately nine more albums. Some were likewise beloved: 1999’s self-explanatory Black Elvis / Lost in Space was a riotous barrage of near-pop songs from “Livin’ Astro” to the corporate-America sendup “The Girls Don’t Like the Job.” (“I want you to fax yourself to China, OK?” he murmurs, almost as an aside. “Do this now.”) But other records were cultier fusillades of shit-talk like 1996’s Big Time (which reunited Keith with his Ultramagnetic MCs pal Tim Dog and called out “all you motherfuckers bitin’ my space shit”) or thornier fan favorites like 2000’s Matthew. (The increasingly loopy “I Don’t Believe You” makes it clear that so far as other rappers go, he doesn’t believe anybody.)

Keith is so reliably prolific and eccentric that it’s easy to assume his work is effortless, in the sense that he doesn’t put much effort into it. But he is fearsomely dedicated to his craft, and hellbent on rarely, if ever, repeating himself. Rather than cravenly build off Dr. Octagonecologyst’s success, he instead invented yet another alias, Dr. Dooom, and kicked off that character’s first album, 1999’s First Come, First Served, with a song called “Who Killed Dr. Octagon?” In 2006, a sequel called The Return of Dr. Octagon emerged with only tentative involvement from Keith himself (it’s complicated); Keith and Dan the Automator reunited for real for 2018’s far better Moosebumps: An Exploration Into Modern Day Horripilation. But with a cult rapper this singular, you are far better off not getting what you want, and far closer to grasping Keith’s whole deal if you consider the possibility that grasping his whole deal has never been the point.


“People get locked into Octagon and I’ll go change—they don’t understand that,” Keith observed in a 2020 chat with The Creative Independent that is legitimately one of the most illuminating rapper interviews I’ve read in ages. “But I’m not here to stay in one thing too long. Some people, they’ll do a gangster album for the rest of their life. Some people will rap fast, like 100 miles an hour, for the rest of they life. I can’t do it all the time. I can’t take antioxidant and just rhyme with that shit every hour. There’s other words to use, you know?” (He’s got a whole riff in that interview about pill-obsessed rappers whose only trick is rhyming antioxidant with apocalypse. Just roll with it.)

The other vexing thing about Kool Keith is that he’s so imaginative, so provocative, so magnificently out there that people assume he really is, say, a murderous alien gynecologist. “It’s just escape for me,” he told The Creative Independent. “But in people’s minds, it’s the opposite: They think I’m in outer space or something. I’m the George Jetson of rap. But I’m in the streets, the hoods, when I write. I write sci-fi things that drive me away from normal daily life. My life is real, but my mind is surreal.”

All of these presumptions and patronizing misconceptions were in the air the one time I saw Kool Keith live, at New York City’s Bowery Ballroom in 2006. I remember three things about this show, in ascending order of importance:

3. When he played “Halfsharkalligatorhalfman.”

2. When I was hanging out at the bar in the Bowery Ballroom basement before Keith hit the stage, and a group of four jovial bearded white dudes standing nearby suddenly started belting out the chorus to the 1972 soft-rock smash “Brandy (You’re a Fine Girl)” a capella, which sure says something about this guy’s core audience, though I’d rather not think about what, exactly.

1. When Kool Keith himself, in the midst of one of his many lengthy and delightful bouts of stage banter, described his writing process this way: “I get me a Yoo-Hoo, I get a motherfuckin’ donut, and I get in they asses.”

What made that image so funny to me at the time was the thought of supernatural oddball Kool Keith doing anything as pedestrian as drinking a Yoo-Hoo and eating a donut, but upon reflection, the real triumph of Dr. Octagonecologyst, as with every Kool Keith album that came after it, is that it’s so bizarre and obscene and sensational that only a real-life human being could’ve thought it all up. What makes this guy truly great is that he thought up the phone number “1-800-PP5-1-Doodoo.” What makes him legendary is that when you call up that number, you never know what, or who, you’re gonna get.

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