It’s Weird ’90s Week on Stereogum. All week long we’re looking at the strangest musical moments and trends of the decade. Check out more here.

The mere existence of Dr. Octagonecologyst would probably merit its inclusion in the Weird ’90s — if there’s a stronger work of art focused around an alien surgeon/gynecologist/halfsharkalligatorhalfman/sexual deviant, I have yet to hear it (I did give The Return Of Dr. Octagon a shot, for the record). This collaboration between Dan The Automator, DJ QBert, and Kool Keith was a culmination of the too-beautiful-to-last period where the music industry was in such robust health that turntablism and horrorcore were considered actual, commercially viable subgenres. But that was the weirdness before the Weirdness: Dr. Octagonecologyst was so popular and so revitalizing to underground hip-hop that Kool Keith had to spend the rest of the decade getting weird enough to undo it all.

Mind you, this was the ’90s — artists of all stripes were tasked with feeling conflicted about any kind of fame, even if they were complicit in seeking it out in the first place. Kool Keith was never a hip-hop purist and would spend a large chunk of the next 20 years criticizing the practices of major labels. Still, Weird ’90s powerhouse DreamWorks reissued Dr. Octagonecologyst, and Automator has lamented that it could’ve sold more copies had it been given better promotion in its initial stage (Keith estimated it moved around 200,000 units). Dr. Octagonecologyst was originally released on Automator’s own Bulk Records and distributed on James LaVelle’s Mo’ Wax, whose next title was DJ Shadow’s mindblowing …Endtroducing; LaVelle and Shadow would would eventually drop UNKLE’s Psyence Fiction, a fascinatingly overblown, star-studded monument/tombstone for electronica and trip-hop that’s mindblowing in an unintentionally humorous way (cue any of the fake endings for “Lonely Soul”).

The problem for Keith was the kind of listeners he attracted with Dr. Octagonecologyst; in short, people like me. In 1997, I was in 11th grade and, like most of my friends, the main if not sole outlets to hip-hop were MTV, BET, and rap radio. Being suburban white kids in Philadelphia, this was somehow considered inherently rebellious. At a certain point in high school, I started hanging out with the skaters because they were the ones who liked Harlem World and When Disaster Strikes as much as I did, but they also seemed more plugged in to what was happening beyond our typical Friday nights of playing GoldenEye and listening to Tool. They were the first people I knew who went to raves and later, the University Of Vermont, and not surprisingly, it was through them I first heard Aphex Twin and the Chemical Brothers and Dr. Octagon.

Before that, I had never heard of Kool Keith in my life. Keith was best known for his work in Ultramagnetic MCs, memorably described as one of the first “all-weirdo” rap duos in a review of their classic 1989 album Critical Beatdown before expanding to a quartet. Keith started writing Dr. Octagon material around 1993, when Ultramag released The Four Horsemen, a last gasp for a group that was overshadowed in their heyday by Native Tongues and Public Enemy, and later surpassed by not only gangsta rap and pop rap but the more streamlined East Coast groups like Gang Starr and EPMD. Even for someone who tried to maintain some kind of budding contrarian streak by favoring West Coast and Southern rap, the most underground stuff I came in contact with was, say, Too $hort or Geto Boys. But Dr. Octagonecologyst’s surrealist, scatalogical subject matter seemed like a failsafe way to make the other guys in my carpool flip out, which was very high on my list of priorities.

I bring this up because to hear Keith tell it, this was exactly the sort of person who was listening to Dr. Octagon, and he had a problem with that. “My three million new fans are white people,” he groused on “Keith Turbo,” from his Black Elvis/Lost In Space album. His enduring statement of this period was cancelling his run of dates for Lollapalooza in 1997, the last year before it went dormant; many assumed he did this out of principle. More likely, he was trying to strong-arm higher appearance fees. During the rest of ’90s, Keith leveraged his newfound visibility with the Sex Style, Black Elvis/Lost In Space, First Come, First Served trilogy, which was presumably meant to chase off Alternative Nation, yet at the same time, gave these new fans exactly what they wanted.

Sex Style was technically Kool Keith’s solo debut, sandwiched between the original and re-release of Dr. Octagonecologyst in early 1997. Judging from its content and release on Keith’s own Funky Ass Records, it was seemingly more along the lines of Beck’s post-Mellow Gold outlier One Foot In The Grave, a grubby, insular work meant to soften the impact of an unexpected hit. Here’s the hook on the first proper track: “Sex style! Niggas want it free, their dogs drink my piss (girls wanna see).” As far as “truth in advertising” introductory lines, it’s up there with “Bring the motherfucking ruckus.”

Now, there are other rap records that worked bluer, but 2 Live Crew or Too $hort or Poison Clan had a sort of aesthetic purity, a functionality that worked in strip clubs or high school locker rooms. Even Keith’s filthiest rhymes weren’t anywhere near as startling as those on Lil’ Kim’s Hard Core, which predated it by several months. While it still serves a powerful feminist retort to hip-hop misogyny, Hard Core had a glossy presentation and catered to fantasy, intended for commercial consumption the same way Boogie Nights or the Playboy Channel was.

Sex Style hit on something much more unnerving — whether it’s the cover or self-explanatory interludes like “Stuck On Pussy Drive,” “What’s He Like?,” “After The Club” and “Lick My Ass,” Keith gave you the sense that this was all taken from his actual life, someone alone in a squalid Sunset Blvd. motel watching blurry VHS tapes, or actually making them himself. And rumor has it that Keith spent all of his DreamWorks advance money on porn. (Side note: A coworker who continued collaborating with Keith in the late 2000s told me he took meetings at the IHOP on Sunset and Orange. I got to hear one side of a phone call with Keith about the possibility of scoring porno flicks.)

Later on the title track, Keith distances himself from horrorcore by calling Sex Style the sole document of “pornocore.” Still, it set the template for pretty much everything Kool Keith would release going forward — a loosely defined concept that he could flit in and out of (he’s a combination of a flasher, an S&M enthusiast, and a pimp — something between Goldie and the Phantom Of The Opera and Blankman), while dedicating most of his time to music industry references, obtuse invocation of athletes, his own catalog and, of course, his dominance over other MCs. Mind you, a lot of Sex Style is about Keith’s, unconventional sexual preferences — “Don’t Crush It,” “Regular Girl,” and the hook of “Make Up Your Mind” (“Who you want to pump the butt?”) are to be taken literally, though “In Your Face” was not.

If all of this was meant to shock the 17-year-old Dr. Octagon newbie, Keith either misunderstood his fanbase completely or understood them too well. Sure, there were cratediggers who’d tell you that Dan The Automator and DJ QBert were the real brains behind the Octagon operation and the relatively brisk sales of the instrumental Dr. Octagonecologyst are a testament to that. But for everyone else, I assume “hilarious skits,” “perverted sex raps,” and “bizarre battle raps” were very highly on the list of what Dr. Octagonecologyst such a bracing listen. Those three things are pretty much all you got on Sex Style.

Sex Style is actually a battle rap album in practice, albeit one where Keith’s lyrical dominance is expressed via anal sex metaphors about 90 percent of the time; the other 10 percent is split about equally between demanding his competitors suck his dick and/or exposing them as transvestites. For a time accused of being overly PC, alternative rap in the ’90s wasn’t exactly #woke.

While bonus track “Get Off My Elevator” ended up on the Office Space soundtrack, the weirdest song here is “Plastic World,” mostly because it has absolutely nothing at all to do with the Sex Style concept. It’s the first of the “Keith Thornton songs” that would pop up on his albums, ones that expressed his disappointment at being misunderstood by the very people listening to them. He expounds on leaving New York because he felt California was actually less fake and he was more interested in listening to E-40 than jiggy rap or jazz-sampling bohos. This was actually the single, and the video features Keith dissing what looks like the Firm in a cowboy hat and a cape. He raps in a project hallway wearing a Kangol and later, eats cereal with a Michael Jackson impersonator.

During the intro of “Plastic World,” Keith mutters, presumably in the voice of a Sex Style skeptic or a DreamWorks exec: “Kool Keith should keep it real, he should rap about space and Mars.” But that’s exactly what happened on Black Elvis/Lost in Space. Once again, Keith’s persona is, at best, loosely defined. He spends about half of it as a transformative black rock star touring with Rage Against The Machine and the like. But then there’s “The Girls Don’t Like The Job,” where he’s an industrial titan looking to move an NBA team to Baldwin Hills, but he’s also a genteel ladies man on “Supergalactic Lover.” And he’s also an astronaut. I mean, I guess his various exploits aren’t that much more incompatible than those of Lucious Lyon.

It’s by far the most approachable Keith album ever made, as there were glances at mainstream trends, particularly Southern hip-hop — a mention of Master P, very low-budget Timbaland interpolations, bounce tracks. “Maxi Curls” hinted at Keith’s disgust with being lumped into alternative rap (“My skin is black, BET”) and yet, Black Elvis does everything possible to establish itself as, well, as an alternative to whatever was happening on the radio at the time. The entire intro distances Keith from Hype Williams’ fisheye-lens fantasies and the most notable guest appearances are from Sadat X and Roger Troutman. As he explained in a 2012 Pitchfork interview, “I was a black rock star making black music, but people didn’t see a black rock star. It was urban, but urban didn’t know what it was because it was too new. I just naturally invaded into rock. All the magazines that covered rock and alternative covered me, but the urban magazines didn’t understand it.” This presented the central contradiction of Keith’s work — he’s correct in that hip-hop should always be a forward-thinking, integrative mode of pop music, though at this point, Kool Keith seemed only conversant with other Kool Keith music.

Enjoyable as it is, Black Elvis isn’t always easy to distinguish from Dr. Dooom, under which First Come, First Served was released. The cover art would appear to be a parody of the legendary Pen & Pixel works that graced most No Limit CDs at the time; as much as I would love to believe Wikipedia here, I doubt that Pen & Pixel themselves had anything to do with it. Dooom kills Dr. Octagon in the first skit, and then the next track, “No Chorus,” is a longform subliminal at Nas for some reason. For the most part, it’s a return to Octagon’s cartoonish horrorcore roots; the sample from “Apartment 223″ was taken from Peter Lorre, and Doom is a cannibal with a taste for Flintstones vitamins and the Staples Singers. It’s hard to tell whether he’s making fun of horrorcore or trying to revive it.

It’s your typical jumble of Kool Keith ideas — in additional to a serial killer, Dooom is also a weirdly benevolent boyfriend (“Welfare Love”), an unreliable landlord (“Housing Authority”), and of course, insult tracks like “You Live At Home With Your Mom” and “I Run Rap” could’ve popped up on basically anything Keith made in the post-Octagon decade. While this preceded Black Elvis, it seemed more intent on ending whatever notion people had of Keith as a marketable entity.

It’s damn near impossible to get through in one sitting, though First Come, First Served closes with “Leave Me Alone,” the most resonant of the Keith Thornton tracks expressing his disillusion with the music industry (if he ever had any illusions to begin with). It’s a consolidation of every aspect from Keith’s overground weirdo phase; you get irresponsible race-baiting (“a white A&R runs the head of black music with a Japanese assistant, what does a Chinese kid know about the rap game?”) and explanations for his erratic behavior (“I cancelled the big tour because I was prepared,” “never got dropped/put my lyrics away and stopped”). More importantly, he reveals the indignities of being branded an “alternative rapper”: dumbass video treatments, having underground rappers insult him with offers to rap on wack jazz loops for a grand and, most pointedly, “I don’t wanna meet Insane Clown Posse and collaborate.” A presumably more practical, and perhaps less principled, Kool Keith appeared at the 2012 Gathering of the Juggalos.

Conveniently enough for the purposes of this feature, there’s a clear cutoff point between “Leave Me Alone” Keith and “get the fuck away from me” Keith, which is the first album he released in the 21st century. 2000’s Matthew has its moments — the totally fucking hilarious “I Don’t Believe You” repeats its title 58 times as the lies become increasingly inane (“You say your pops is cool,” “You own a Dodge truck,” “You selling Knicks tickets”) and “Extravagant Traveler” is a funny enough ripoff of “No Chorus,” and hey, that’s actually Kool Keith outside of his apartment in North Hollywood on the cover. But otherwise, Keith raps in the sort of tone you only hear from people when they’re dealing with their cable provider or find out they got a parking ticket. He’s pissed about the state of the music industry, but this time he names names…unfortunately, most of it is leveled at the universally accepted OutKast, specifically Andre, for presumably stealing his wigs, co-opting “3000,” and trying to be Jamaican (?). I swear, I’ve seen it theorized that Andre was clapping back at Keith with the “What’s cooler than being cool?” line from “Hey Ya,” as if Andre 3000 was even remotely aware of Keith’s ire, let alone willing to put his debut solo single in jeopardy to settle a beyond-minor beef. But then again, that was more or less how you had to operate as a Keith fan going forward — you had to share his sense of persecution. Every now and again, he’d pop up and offer specious accusations about him being ahead of his time.

The weirdest part? He was kinda right. It just took about a decade for any of the bullshit he spouted to be backed up by any legitimate evidence. In the meantime, he spent most of the 2000s rehashing his past work — Spankmaster is Sex Style 2, albeit with actual horrorcore guy Esham, “Big Trucks” birthed the Diesel Truckers concept, 2007 saw a new and roundly ignored Ultramagnetic MCs album and he eventually made both The Return Of Dr. Octagon and Dr. Dooom 2, which I’m pretty sure I reviewed but have no recollection of ever hearing.

Starting around that time, many of the biggest rappers were starting to operate in a Keith-like manner, even if it was more a matter of correlation than causation — Lil Wayne and Future have presented themselves as both aliens and astronauts, though that concept dates back far beyond Keith to Sun Ra, Funkadelic, or any number of formative Afrofuturists. It’s infinitely more likely that drugs were responsible for Lil Wayne’s Martian phase than Black Elvis (as well as his rock star turn on Rebirth), but it did provide a means for re-appreciating Keith when his credibility was at its lowest point. Likewise, it was easier to engage with Lil B’s data dumps when Keith was basically releasing based albums and expecting people to pay $17 for them. There are points on Dr. Octagonecologyst where you can hear embryonic Odd Future and SpaceGhostPurrrp, while Father’s Who’s Gonna Get Fucked First? sure feels like the progeny of Sex Style, if not direct homage. And these days, iLoveMakonnen sounds a hell of a lot like Keith.

Weirder yet? Keith hasn’t really used this opportunity to gloat. When he spoke to me back in 2012, Keith mused, “I put another extra 20 years on rap. Some people take what I do and run with that only, so they can’t go further,” and it sounded like someone in acceptance rather than defiance. After two decades of berating any rapper, real or imagined, who sounded even remotely like him, he realized that might actually be the way rap moves on to the year 3000.