Kool Keith captured the hearts and minds of the public with his Dr. Octagon character but to better understand the man and his legacy we need to understand how his personality shaped his characters.

Kool Keith is a hard man to decipher. The man behind Dr. Octagon once told a reporter that he was sent to Bellevue Psychiatric Hospital after going mad and attempting to eat his own hand as a lark. But for those who know the landscape of the subterranean rap scene, Kool Keith, the original “weirdo rapper” has been a name to behold for decades.

His off-kilter and nebulous lyrics preceded the likes of MF Doom and Canibus. As part of the Ultramagnetic MC’s hip hop group, Kool Keith relished in providing audiences with references to science, an expansive vocabulary, and subversive rhymes.

However, Keith is perhaps most known for his Dr. Octagon persona. The character is to music what William S. Burroughs’ Dr. Benway was to literature. A character so hilariously sinister in his lack of conscience, with erratic raps about murder and sex that became a cult phenomenon.

The Absurd World of Dr. Octagon

While Kool Keith didn’t adopt his more futuristic raps until his solo career, his style was definitely still verbose as part of the hip hop group Ultramagnetic MCs. On “Ego Trippin”, he raps:

“They use the simple back and forth, the same old rhythm

That a baby can pick up, and join right with them

But their rhymes are pathetic, they think they copacetic

Using nursery terms, at least not poetic”

Keith was purposefully rapping long multisyllabic words and using assonance, proving he was years ahead of his time. Keith was not afraid to experiment, and on his solo debut he unveiled the character known as Dr. Octagon.

His debut effort Dr. Octagonecologist had Keith rapping from the perspective of an alien surgeon called Dr. Octagon from the year 3000. Lyrically, Keith developed a style of imposing red herrings where he essentially subverted the listener’s expectations and introduced non-rhymes in his bars. Adding to the mystique was the spacey production by Dan the Automator who helped Keith in his worldbuilding with an atmospheric soundtrack. Dr. Octagon helped usher in a new era of alternative rap as it experimented with song writing structure; introducing stream of consciousness rap lyrics, with ethereal sounding production. There was nothing else like it.

The first single, “Earth People,” immediately transports the listener into the mind of Dr. Octagon, and perfectly describes who he is for the listener; and helps establish the lore of the Dr. Octagon character. While the other standout track “Blue Flowers,” references Philip K. Dick’s A Scanner Darkly and alludes to recreational drug use. Its eerily psychedelic production backs up Dr. Octagon orating the story, and his philosophy regarding saving patients, while also dealing with the philosophical nature of transhumanism. On “Blue Flowers,” he raps:

“Cybernetic microscopes and metal antidotes

Two telescopes that magnify size of a roach

Three computers, the cup of coffee planted with my hand and

Astroplanet detached, turn on rear foggers

Cut the light on the kid, and turn the bright on

Supersonic waves combine and burn as brainwaves”

Dr. Octagonecologist is credited with opening up the genre to new sounds, previously unheard of in hip hop; mixing electronic, trip hop, psychedelic, horrorcore, and old school hip hop into a hodgepodge of an album. Dr. Octagonecologist presented an unorthodox approach to hip hop not seen since the days of Native Tongues. Its unusual and unsettling soundscape helped birth a fanbase for unconventional sounds. Using surrealist and absurdist lyrics, Keith paved a path for rappers to be more abstract rather than the gritty realism that the ‘90s era was known for. Acts like Deltron or MF Doom may never have found a home without Dr. Octagon.

Dr.Octagon - Blue Flowers

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While the album is praised by hip hop heads and critics alike, Keith has become a lot more critical of the album later in life for only appealing to white audiences, which turned him from an indie darling to contemptuous rabble-rouser in the eyes of various publications.

Killin’ Your Darling: The Rise of Dr. Dooom

Dr. Octagon became a cult phenomenon. So Keith in his contrarian nature decided to kill him off, creating a character named Dr. Dooom on the album First Come, First Served for that exact purpose. The Dr. Dooom album took on a darker tone, and was meant to tether Keith back to reality. However, the album wasn’t based in realism, and instead served as an extension of Kool Keith’s alter egos.

Songs like, “Apt 223,” or “Neighbours Next Door,” help create a surreal dark atmosphere that eclipsed the morbidity of even Dr. Octagon. The Dr. Dooom character, turns out, is a cannibalistic serial killer living in the housing projects.

The album is filled with horror-movie imagery. “Apt 223,” starts with Dr. Dooom warning listeners not to ring the bell as “the spirits around will haunt you”; it’s believed that the name of the track is a reference to “Apt 213,” which was Jeffrey Dahmer’s Milwaukee apartment where Dahmer hid the bodies of his victims. The “I’m Hungry,” vocal sample heard throughout is from an old 1960’s radio show, Arch Oboler’s Drop Dead.

The Dr. Dooom character also went even further than the Dr. Octagon character in subverting listeners’ expectations as Keith would then rap in full non-sequiturs. On “Apt 223,” he raps:

“With the eighth body in my trunk my elbow bleeds with lumps

Walkin from the sanitation dump with rotten skulls

On my waterbed with Miller beer kegs

Blood in my cabinet, ears in my closet

Watchin the Raptors play the Houston Rockets

With your arms in the freezer I grab a icicle

Puttin fingerprints on my bicycle”

While Dr. Octagon was dead, Kool Keith had room to maneuver his off-beat style without the same expectations. Keith would continue on the tradition of building different personas on subsequent albums, most notably the Black Elvis/Lost in Space album; a reclamation of the sci-fi themes explored on Dr. Octagonecologist.

The (Unsanctioned?) Return of Dr. Octagon

10 years after creating one of the most iconic alternative rap albums, the Dr. Octagon character was brought back to life. In 2006, rap audiences were surprised to hear about an album reviving the Dr. Octagon character entitled The Return of Dr. Octagon. Though its place in canon is debatable.

An 8-part viral campaign entitled “The Decipher Series: Seeds to the Return of Dr. Octagon” with accompanying comic book storyline and music were posted to various message boards on the net. Several artists released songs as bread crumb trails hinting at the return of Dr. Octagon. Out of the eight dj mixes, the most notable was a song aptly titled “A Gorilla Driving a Pickup Truck,” mixed by Rob Sonic; which was exactly what the title promised. The ever-idiosyncratic rapper seemed to continue with the tradition of putting out wacky concepts.

Dr. Octagon - A Gorilla Driving a Pickup Truck (Rob Sonic Mix)

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The album had a buzz going for it, but it was plagued by behind-the-scenes politics. The original producer slated for the project, Fanatik J, decided to drop out of the project after failed negotiations with record company, CMH, and a falling out with Keith. Part of the problem was that the label had taken over ownership rights. So instead of Fanatik J, the production was handed over to Berlin production team, One-Watt-Sun, created by the label.

Apparently, the production team gave Keith loose topics to rap about. These songs became what is generally considered the best of the project, namely; “Trees,” “Ants,” and “Aliens.” These three individual songs definitely stand as a testament to the creative genius of Kool Keith. “Trees,” sounds like an electro-pop record that promoted concern for the environment long before environmentalism became vogue. “Ants,” is a play on the idea of worker bees, and instead describes the plight of the workers and anthropomorphizes ants as workers and speaks on the plight of the common man with witty wordplay. While “Aliens,” revisits the sci-fi concept explored on the original Dr.Octagon, as the beat incorporates elements of ska as it progresses.

Afterwards, Keith himself got entangled with contract negotiations. Keith then earmarked old vocals he recorded two years before to get out of his contractual obligation.

None of Fanatik J’s production made it to the final release. Keith ultimately gave his blessing for the album but it remains a contentious album within hip hop circles. Keith himself has mixed feelings as he liked the production but felt it hurt his reputation as an artist.

Dr. Dooom 2: The Killing of Dr.Octagon, Revisited

Following The Return of Dr. Octagon was Dr. Dooom 2. The album is less fleshed out than First Come, First Served but is a highlight into Kool Keith’s brand of musical insanity that includes the track “Run for Your Life,”. The album contains more homages to horror with lines like:

“I put the Wolfman on the guestlist for one of my shows

Watch the Invisible Man pluck boogers out his nose

The mummy get out his Fleetwood and smack all his hoes”

These cartoonish raps also paved the way for quirky future rappers like Action Bronson or MF DOOM. While the Dr. Dooom character wasn’t firmly developed, it certainly showcased the potential for rap to think outside the box. Dr. Dooom wasn’t pigeonholed to be a sci-fi caricature but was able to develop his own lore.

Kool Keith - R.I.P. Doctor Octagon - 2/26/2009 - Mezzanine

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Being a Dr. Dooom album, there is of course a track where he kills Dr. Octagon. Again. “RIP Dr. Octagon,” has Dr. Dooom explain how Dr. Octagon was killed and revived and killed once more. Picture Dr. Dooom trying to hold Dr. Octagon head’s underwater but Dr. Octagon continues to struggle and fight. Dr. Dooom tries over and over again mentioning various execution attempts but Dr. Octagon is propped up by people with a respirator and major labels. Keith as Dr. Dooom sounds fed up, saying that he has beaten that character to death and was forced to be more commercialized. The hook declares, “no wack remixes”, a nod to record label CMH’s remixing of his vocals.

Moosebumps: An Exploration into Modern Day Horrorpilation

Finally, in 2018 Keith decided to revive the Dr. Octagon character once more and brought back original producer Dan the Automator and DJ Qbert to make a true sequel. Moosebumps opens up with “Octagon Octagon” which states Octagon is back and is making headlines. The track also samples part of “Earth People,” which is featured on the original Dr. Octagonecologist.

Kool Keith also acknowledges the influence of George Clinton, referencing him on the track, “Operation Zero”. As this album is likely a look back on his career, these parallels make sense. Like Clinton, Keith developed alter egos of himself to better negotiate record contracts, much like how Clinton used Parliament and Funkadelic split as two different acts for business leverage.

Moosebumps: An Exploration into Modern Day Horrorpilation feels like a true spiritual successor to the first Dr. Octagon album. The true return of Dr. Octagon is a triumph for a career that has been beleaguered by mediocre releases in the 2000’s. Moosebumps works as a creative challenge for Keith, who strived to balance the perversion of his Dr. Octagon character in the wake of the #Metoo era. The Dr. Octagon on Moosebumps sounds revitalized, paying tribute to his earlier work while modernizing the concept for a new age. Moosebumps is truly a return to form.

Keith had spent a large part of his career moving away from the Dr. Octagon character only to embrace it later in life. He kept experimenting, molting like a snake, shedding the layers of himself with various incarnations. Each incarnation renewing his creative spirit.

Without a doubt, there is more to Kool Keith than just Dr. Octagon. Unpacking that is unfortunately beyond the scope of this article. What can be said, however, is that without Dr. Octagon, audiences would not see Kool Keith’s full personality.

Using Dr. Octagon as a lens for better understanding Kool Keith, we see an innovative artist who was years ahead of his time, imbuing traits of his personality in various personas with a deft hand. His humour and wit, helped to establish that hip hop could be non-serious, if not downright quirky. The New York Times has aptly described him as a cross between Marquis de Sade and George Clinton.

Keith as Dr. Octagon detonated explosive works of art into the structural foundation of hip hop. Dr. Octagon reformed and reshaped what could be considered hip hop and demonstrated how abstract it could go. Dr. Octagon was postmodern, post-structuralist, and above all original. Kool Keith’s legacy is perhaps best summed up with one of the original Dr. Octagon skits:

“Oh shit — there’s a horse in the hospital!”