Dr. Octagon: The Story Behind Hip Hop’s Masters Of The Surreal

Illustration by Dan Redding

Dr. Octagon are back this year with a new album and tour. In honor of the group’s return, let’s take a look back at the origins of the twisted trio and their debut album.

The surrealist hip hop masterpiece Dr. Octagonecologyst (released in the U.S. on May 7, 1996, on Bulk Recordings) is a milestone of hip-hop’s coming of age. The rap genre was less than two decades old in 1996, and it had matured from the relative innocence of its formative years to the politically-charged gansta rap era of the early nineties. Suddenly, hip-hop’s first truly surreal rap album arrived from visionary lyricist Kool Keith, ascending producer Dan the Automator, and legendary turntablist DJ QBert. Dr. Octagonecologyst was a boundary-skewing mindwarp so fresh and bizarre, it seemed as if it had been sent from Jupiter. Here’s the story of the groundbreaking album.

Kool Keith built his reputation as the breakout star of Queens hip hop crew Ultramagnetic MCs, known for their hits ‘Ego Trippin’ and ‘Poppa Large.’ By the time Ultra dissolved, Keith was ready to move on. What his fans didn’t know was that the young rapper had been harboring a pent-up tsunami of weirdness – and he was about to find the perfect project to unleash it on.

Keith moved to Los Angeles looking for a change. During an interview with The Combat Jack Show, Keith recalled thinking, “New York is dry right now, nothing’s happening.” California’s pimp culture and palm trees provided ample inspiration for Keith and producer KutMasta Kurt, who were at the beginning of a very long and prolific collaborative partnership. The two friends shared an apartment while they began work on the album that would become Sex Style.

According to Brian Coleman’s superb book Check the Technique: Volume 2: More Liner Notes for Hip-Hop Junkies, the Dr. Octagon concept emerged from demos created at this time, including early versions of the songs ‘Dr Octagon’ and ‘Technical Difficulties.’ When Kurt’s friend Dan the Automator heard the Octagon demos, he said, “Tell Keith I want to do a whole project with that stuff.”

Like Keith, Dan the Automator had also been feeling frustrated with the stagnant state of hip hop. “I loved hip hop in the mid-’80s,” Automator told the Chicago Tribune, “where you had all these different characters – one guy was doing electronic beats, somebody else was using really dirty samples, people were making party records, political records. Then you turn the clock to ’92, and suddenly everybody in L.A. is like `Check out my Lexus, count my money.’”

Keith and Automator made an agreement, and Keith soon began making trips Automator’s San Francisco studio – known as The Glue Factory – which was located in his parents’ basement. The pair worked together to push the boundaries of what hip hop could be. Keith described the experience of making the album during his appearance on the Combat Jack Show: “I went up there [to San Francisco], got some Yoo-Hoos and donuts, stayed up there for like seven days, and we came up with Octagon. Octagon was a gynecologist, crazy, combined with sex and everything mixed in the gumbo pot – doctor, medical. And the shit jumped off to every genre: the techno world, the rock world, the rap world, alternative.”

‘Dr Octagonecologyst’ cover art by Pushead

Kool Keith’s fractured, kaleidoscopic wordplay on Dr. Octagonecologyst represents an advance for the art of the hip hop lyricist. His hallucinogenic stream-of-consciousness verses were a left-field blast of fresh air during an era dominated by stark street realism (Nas’ untouchable Illmatic) and Wu-Tang’s hip hop eclipse (Raekwon, GZA, and Ol’ Dirty Bastard all released solo albums in 1995).

Consider this line from ‘Blue Flowers Revisited’: “Dr. Octagon, paramedic focus on the East / For priests, my anesthetics prescribe a certain fertilizer.” The content reveals the abstract medical themes of Dr. Octagon – but more importantly, this rhyme couplet reveals Keith’s experimentation with structure. Instead of placing a rhyme at the end of each line, Keith connects the end of the first line (‘East’) with ‘priests’ at the beginning of the next. The rest of the phrase doesn’t rhyme at all. Keith had transcended the rhyme styles of old-school hip hop and was experimenting with more advanced techniques.

Keith and Automator formed the nucleus of the Octagon team, but Dr. Octagonecologyst also bore the fingerprints of DJ QBert, cover artist Brian ‘Pushead’ Schroeder (best known for his iconic work with Metallica), and guest emcee Sir Menelik. This fleeting collaborative union was never to be reproduced. Dan told author Brian Coleman that he and Kool Keith never performed a single live date together as Dr. Octagon (although the group did manage to make one video, for ‘Blue Flowers,’ see above). Keith abruptly killed the Dr. Octagon character on his 1999 album First Come, First Served. The name Dr. Octagon was later revived on several Kool Keith releases of dubious quality or authorship (The 2006 release The Return of Dr. Octagon was released without Keith’s consent). Dr. Octagonecologyst is the only true Dr. Octagon album.

Dr. Octagonecologyst was the source of some discord between collaborators and friends Automator and KutMasta Kurt. While the Octagon album had been primarily produced by Automator, it had originated in demos produced by KutMasta Kurt, who retained production credits on two of the album’s songs. In 2008, Kurt told The A.V. Club that he had to sue Nakamura for his royalties. Kurt explained, “I got the whole [Dr. Octagon] thing started and really got nothing directly out of it. [Automator] ran with it, but he never gave credit to the person who threw the ball. At the end of the day, I actually had to sue the guy. They settled, but I actually had to file… Dan did well and good for him, but you meet the same people on the way up as you meet on way down.”

The album was released in several versions, first as Dr. Octagon in 1996, and again with added tracks as Dr. Octagonecologyst on Dreamworks in 1997. “This album turned me into a rock star,” Keith told Combat Jack. “I was no longer an average rapper.” Reviews were favorable but not the reception of an instant classic: the New York Times called it “one of the most progressive rap projects to be released in the past year” and The Source awarded it 3.5 mics out of 5.

The album’s influence is undeniable. Keith wasn’t hip hop’s first eccentric, but he pushed the doors open wider for experimentation and non-traditional subject matter. Human memes like Lil B and RiFF RAFF have thrived in contemporary rap in part because Kool Keith paved the way with his demented personas. But it’s the boundary-busting innovations of Dr. Octagonecologyst that matter most. Innovation of this caliber is a virtue in any genre, in any era.