Around 1995, Kool Keith’s path was unclear. After the demise of his legendary New York crew Ultramagnetic MCs, he spent many of his early solo years out in California. Rap had never paid him or his crew the recognition they deserved, and Keith’s place within it seemed unstable. Collaborator Kutmasta Kurt had been working with him on an album for Capitol called Sex Style—a porno-chic concept record that the label continually back-burnered. Keith needed something else to get his voice out there in the meantime.

Inspired by his West Coast relocation, Keith cut another track and sent the tape to hip-hop radio tastemakers like Stretch & Bobbito and Sway & King Tech. His name wasn’t on it; still, his voice was recognizable enough that people knew it was him. But the lyrics—with a space-doctor, scato-gyno-urological theme, and co-penned with an NYC cohort named Sir Menelik (as “Chewbacca Uncircumcised”)—were completely preposterous. “Wax in your inner ear, doodoo in your outer ear/Two cows a zebra will jump through your atmosphere,” goes the project’s titular cut. The DJs assumed it was more fitting to bill the track to the only name listed on the cassette: Dr. Octagon.

The positive reception for “Dr. Octagon” caught the attention of Dan Nakamura, aka Dan the Automator. A young producer who had been learning on the job, he mastered early Solesides Records by the likes of DJ Shadow and Latyrx in his studio The Glue Factory (or as his parents knew it, their basement). Keith and Automator wound up doing a couple albums’ worth of collaborations in ’95 and 1996—a host of their bicoastal boom-bap joints can be heard on the after-the-fact collection A (Much) Better Tomorrow—but it’s Dr. Octagonecologyst that really shook people up. Hip-hop could be weird, but how weird could it get? The level of oddity within Dr. Octagonecologyst had yet to be explored. And we wouldn’t be getting this nice deluxe reissue of the album if that weirdness hadn’t aged well.

At a time when 1980s vets were accustomed to fall-offs, Kool Keith’s second act was inspiring, and it came from a relentless willingness to redefine himself—even if it meant being someone else. On the album, he’s credited as Dr. Octagon throughout, even if his dissociative, Thelonious Monk-timing bars are consistent with his other guises. Few MCs have been as comfortable in their absurdity, their convention-trashing, or their absolute fearlessness in trying new things on the mic. Dr. Octagonecologyst is where Funkadelic at their most “Icka Prick”-pornographic is rerouted into intergalactic g-funk, a place too cold for drop-top Impalas. Cronenberg body horror dominates throat-clenching medical-procedure narratives, like “Waiting List” and “Blue Flowers.” Residual Sex Style fantasies drive “Girl Let Me Touch You,” and “I’m Destructive” pushes threats of cruelty to the point of total goofiness. But when Keith is on the mic, he never lets up for a breather. Even at their most meter-defying and non sequitur-prone, his lyrics are memorably pungent in pretty much every line.

As Automator produced with a singular defiance, all that strangeness found its ideal pairing. No slight to Ced Gee and the Ultramagnetics, but this is where one of the great unconventional MCs found his most adventurous co-experimentalist. Nakamura was a keen-eared cratedigger and a trained violinist—that’s him splitting the difference between reverie and nausea on the “Blue Flowers” loop. He paired obscure yet on-point samples with more recognizable classic drum loops (including a nod to Ultramagnetics-popularized “Synthetic Substitution” on “Wild and Crazy”) and raw, ugly keyboards. It gave Dr. Octagonecologyst the feeling of a traditional hip-hop record sent through a bath of acid—lysergic or corrosive, take your pick.

On the more accessible cuts, he takes familiar, contemporaneous concepts and scuzzes them up. “Earth People” pairs Whodini 808s and fizzing analog synth sounds, resulting in a horror-psych mutation of classic Dre. It also features DJ Q-Bert’s then-new idea of running his turntables through a wah-wah pedal for a mind-warping scratch outro. The album’s less conventional moments show how Automator could have a hard time thinking of this as a hip-hop album at all, despite it showcasing an all-time rapper’s-rapper. Coyote howls dropped like Bomb Squad Maceo horns during “On Production.” Headnod beats bumped skulls into musique concrete Moogs on “Biology 101,” ratcheting up the uncanny elements of Keith’s presence. But Keith and Automator linked up their sensibilities so well that even their jokey, free-associative skits became indelible. Say it with me now: “Oh shit, there’s a horse in the hospital!”

The additions to this reissue of Dr. Octagonecologyst don’t dilute that feeling, either. The three previously unreleased tracks are in keeping with the album’s space-perv aesthetic: “Astro Embalming Fluid” sews together headknock beats, silver-plated synth burbles, and manic mid-freakout astronaut lyrics. “Redeye” finds common ground with Roger Troutman and Master P before going into zoological player mode. And “I’ll Be There For You” posits the Doctor as some sort of extraterrestrial savoir in a track that would’ve made for a strangely uplifting respite. Apart from that, the two Automator remixes—a somewhat more “professional” sounding guitar on “I’m Destructive” and a lesser version of “Wild and Crazy” with a subtler synth bassline—hint at directions that Dan might’ve taken these tracks with a few more years of experience. In these cases, the happy accidents of amateurism win out over the older-and-wiser versions.

Dr. Octagonecologyst’s afterlife is nearly as weird as its conception and its essence. Seemingly destined for cult status, it instead spread like wildfire, becoming an indie-rap essential—even as both parties were en route to newer things. By 1997, when Dr. Octagonecologyst’s major-label push made it the single weirdest thing to ever have the DreamWorks name attached, both its MC and its producer were on to the next thing. Their respective careers would lead Automator to a string of alter-egos—Handsome Boy Modeling School with Prince Paul, Deltron 3030 with Del the Funky Homosapien, and most notably Gorillaz with Damon Albarn. Meanwhile, Keith would kill off Dr. Octagon for Dr. Dooom, only to resurrect him again for an inside-out, meta-alter-ego: Mr. Nogatco. Whether they’re inspired by its precedent or pushing back against it, both artists wound up permanently routed towards definitive careers by Dr. Octagon. And even considering its 1990s origins, Dr. Octagonecologyst still feels as much out of its time as it does out of its mind.