15. Poppa Large (with Ultramagnetic MCs) (1992)

“Poppa Large,” from Ultramagnetic MCs’ 1992 album Funk Your Head Up, is Kool Keith at his most iconic, though the remix steals the show. The album version, produced by Ced Gee, drags with a dull beat and Keith’s oddly flat delivery, a lackluster cut that hints at untapped potential. The remix, released as a single, transforms it into a banger—crisp drums, funky bass, and a vibrant loop unleash Keith’s manic energy. His wild, boast-heavy rhymes, delivered with unhinged flair, paint him as Hip Hop’s mad genius, backed by a video showing him in a straightjacket, caged like Hannibal Lecter.

This remix became a cult hit, its infectious groove and Keith’s chaotic flow making it a standout in his catalog. Frustratingly, Funk Your Head Up omitted the remix, even as a bonus, leaving fans who bought the album shortchanged. Still, the single’s frenetic vibe captures Keith’s Ultramagnetic peak, a must-hear for its bold, unfiltered swagger.

14. Freaks (2003)

“Freaks,” from Kool Keith’s 2003 The Lost Masters, is a quirky gem buried in a patchy collection. Pulled from the first of three Lost Masters releases, the track emerges from Keith’s prolific, often inconsistent output, where quality control takes a backseat. Like Ultramagnetic MCs’ obscure B-sides, these “lost” cuts—studio experiments and rough sketches—rarely justify daylight. The beat feels half-baked, with a repetitive loop and thin drums that don’t quite land. Yet, Keith’s charm saves it. His bizarre, sex-drenched rhymes, delivered in that slippery, off-kilter flow, spin tales of oddball desire, while the sticky hook lodges in your brain.

Not a polished banger, “Freaks” thrives on its raw weirdness, a highlight alongside “Girls Want You” in the strongest Lost Masters set. It’s not for casual listeners—Keith’s freaky imagery demands a taste for the absurd. Still, this track’s infectious oddity proves why diehards like us keep digging through his chaotic catalog. We know we probably shouldn’t, but we love this song.

13. Happy New Year (1996/2016)

“Happy New Year,” from Kool Keith’s 2016 release Your Mom Is My Wife (recorded around 1996–1997), is a chaotic snapshot of his unhinged genius, guided by KutMasta Kurt’s deft production. Kurt, alongside Dan the Automator, is one of the few producers who can harness Keith’s wild fetishes and multiple personas into cohesive tracks. Here, over a lean 23-minute project, Kurt’s gritty boom bap—punchy drums, warped synths—grounds Keith’s bizarre rhymes. This track’s hook, a strange earworm, pairs with lyrics diving into his obsessions: pornography, rectums, animals, and disses to wack MCs, all delivered in his slippery, provocative flow.

Keith’s output often swings from brilliant to unlistenable, but Kurt keeps “Happy New Year” tight, avoiding the excess that bogs down Keith’s self-produced work. Not a chart hit, it’s a cult cut for fans who relish his vulgar, trampling disregard for taste. Part of the Your Mom archives, it captures Keith’s ‘90s peak—weird, lewd, and magnetic, a freaky gem that thrives in its Kool Keith’s bizarness.

12. Diesel Truckin' (2004)

“Diesel Truckin’” featuring MC Dopestyle from Kool Keith’s 2004 album Diesel Truckers with KutMasta Kurt, is a vibrant return to form. After divisive releases like Matthew and Spankmaster, where Keith’s self-produced tracks veered into repetitive fetishism and anti-rapper rants, this collaborative album reignites his spark. Kurt’s production on “Diesel Truckin’”—booming bass, crisp drums, and funky loops—drives the track, crafting an earworm hook around trucking imagery. Keith’s flow, loose yet sharp, paints vivid scenes, blending quirky brags with his signature oddball charm, while Dopestyle’s gritty bars add muscle.

The track shines as a centerpiece of Diesel Truckers, a 53-minute ride that feels fresh, not forced. Keith sounds engaged, trading dour tirades for playful energy, a nod to his Ultramagnetic roots and Dr. Octagon flair. We like it for its fun vibe and tight chemistry, proving Keith thrives with a producer like Kurt steering the wheel.

11. Bay-Bronx Bridge (with Masters Of Illusion) (2000)

“Bay-Bronx Bridge,” from the 2000 album KutMasta Kurt Presents Masters of Illusion, is a nostalgic banger uniting Kool Keith, Motion Man, and producer KutMasta Kurt. Kurt’s beat—crisp old-school drums, funky bass, and subtle scratches—evokes Ultramagnetic MCs’ raw Bronx energy, grounding the track in Keith’s roots. Keith’s flow, sharp and unhinged, delivers vivid brags and surreal jabs, each verse a playful yet lethal dart at wack MCs, wrapped in Kurt’s head-nodding production.

A standout on the cult classic Masters of Illusion, this track never hit mainstream radar but thrives in underground circles, the 60-minute album one of Kool Keith’s best albums. “Bay-Bronx Bridge” is a bridge between coasts and eras, a tight dose of Hip Hop’s oddball charm, demanding replays for its infectious vibe.

10. Kool Keith Housing Things (with Ultramagnetic MCs) (1988)

“Kool Keith Housing Things,” from Ultramagnetic MCs’ 1988 debut Critical Beatdown, is a sharp showcase of Keith’s early brilliance. While any track from this landmark album could fit this list, we chose this cut because it features Kool Keith solo. Produced by Ced Gee, the beat hits hard—chunky drums, funky bass loops, and scratched samples create a quintessential ‘80s boom bap vibe. Keith’s flow, confident and playful, weaves braggadocio with quirky wordplay, laying the groundwork for his future eccentricities, spitting lines that flex his mic dominance with a sly grin.

Not even the album’s standout—tracks like “Ego Trippin’,” “Break North,” “Ease Back,” “Watch Me Now,” or “Give the Drummer Some” compete fiercely—it still captures Keith’s foundational role in Ultramagnetic’s game-changing sound. Critical Beatdown is a Hip Hop cornerstone, and this cut, though less heralded, pulses with the group’s innovative energy. For fans tracing Keith’s roots, it’s a potent dose of his nascent genius, brimming with Bronx swagger.

9. Apartment 223 (as Dr Dooom) (1999)

From Kool Keith’s 1999 album First Come, First Served, “Apartment 223” unleashes his Dr. Dooom persona in a grim, horrorcore masterpiece. KutMasta Kurt’s production—haunting keys, stark drums—crafts a suffocating backdrop, amplifying Keith’s deranged narrative. As the cannibalistic landlord, Keith paints a grotesque routine of body bags and blood-stained fridges with eerie nonchalance, his flow weaving precise chaos. The track’s dark humor, a hallmark of Keith’s absurdity, twists horror into satire, sidestepping gimmicks for raw menace. Unlike the sci-fi gloss of Dr. Octagonecologyst, this cut embraces gritty, unpolished dread, a bold middle finger to mainstream expectations.

“Apartment 223” pulses with unhinged creativity, its vivid imagery lingering like a bad dream. Kurt’s claustrophobic beats mesh perfectly with Keith’s unfiltered vision, carving a niche for underground devotees.

8. Keep It Real... Represent '96 (1997)

“Keep It Real… Represent ‘96,” from Kool Keith’s 1997 album Sex Style, is a wickedly sharp diss track aimed at wack rappers cloaked in his signature perversion. KutMasta Kurt’s production—a gritty blend of funky bass and minimalist synths—evokes a sleazy, ‘70s adult-film vibe, perfectly framing Keith’s unhinged delivery. Keith transforms standard rap bravado into a twisted assault, spitting sexually charged barbs like “I heard you quit rap, your wife went back to porno flicks / You turned drag queen, a call girl doing tricks.” His deadpan sneer and intricate wordplay elevate the crude humor, making each insult land with unsettling precision. Far from a throwaway, the track reveals Keith’s lyrical dexterity, turning grotesque metaphors into dark comedy.

Part of Sex Style’s bold “pornocore” vision, this song thrives in its audacious weirdness, a testament to Keith’s refusal to bow to mainstream norms. Its biting satire and provocative edge make it a standout, though our love for its twisted brilliance might hint at an unhealthy fascination with Keith’s chaotic mind.

7. Blue Flowers (as Dr Octagon) (1996)

“Blue Flowers,” from Kool Keith’s 1996 masterpiece Dr. Octagonecologyst, is a haunting episode of his Dr. Octagon persona, a time-traveling, hypersexual gynecologist from another dimension. Dan the Automator’s production weaves an eerie tapestry—creeping violins, wah guitar, and sparse drums—creating a cinematic, alien soundscape. Keith’s vocals, introduced with “Dr. Octagon, paramedic fetus of the East,” are a surreal cascade of medical jargon and cosmic absurdity, delivered with a menacing calm. DJ Q-Bert’s frenetic scratches, twisting a human scream into cartoonish chaos, amplify the track’s unsettling edge. The chilling chorus, paired with Keith’s vivid, disjointed imagery, pulls listeners into a warped operating room where horror meets dark comedy.

“Blue Flowers” blends experimental finesse with underground grit, redefining Hip Hop’s boundaries. Its hypnotic strangeness, a bold counterpoint to ‘90s mainstream gloss, cements its status as a genre-defining gem.

6. Sex Style (1997)

“Sex Style,” the title and opening track from Kool Keith’s 1997 album Sex Style, is a bold plunge into his self-coined “pornocore” realm, brimming with raw audacity. KutMasta Kurt’s production—grimy basslines and ominous synths—channels a lo-fi ‘70s adult-film grit, setting a sleazy stage for Keith’s unfiltered chaos. His flow, erratic yet razor-sharp, unleashes surreal, graphic lines like “N***** want it free / Their dogs drink my piss,” blending perverse imagery with twisted humor. Unlike the diss-heavy “Keep It Real… Represent ‘96,” this cut dives deeper into Keith’s obsessive fantasies, his voice a sneering guide through a feverish mind.

This track, a centerpiece of Keith’s most daring solo work, thrives on its unrelenting weirdness, rejecting mainstream polish for provocative originality. Kurt’s sparse beats amplify Keith’s eccentric bars, creating a hypnotic, unsettling vibe. Its dark, playful edge captures Keith at his most untamed, a polarizing gem for those who revel in his taboo-busting vision.

5. Bizarre (with Ultra) (1994)

“Bizarre,” from Kool Keith and Tim Dog’s 1994 album Big Time, is a raw plunge into Keith’s deviant mind, a cornerstone of his eccentric path. The production—grimy drums, throbbing bass, eerie synths—builds a dark ‘90s boom bap vibe. Keith’s verses, wild and provocative, revel in absurdity, from praising a giraffe’s “pretty ass” to grotesque fantasies about bombs, ammonia, and Sugar Smacks, perhaps intended as slyly mocking Hip Hop’s shallow bravado. His slippery flow dances over Tim Dog’s gruff complaints about being dragged to a zoo in the intro, their banter framing Keith’s fetishes—giraffes, baboons, alligators—in vivid, unsettling detail. Tim’s straight-man role anchors the chaos, letting Keith’s unhinged charm shine.

“Bizarre” and the rest of Big Time thrive as a cult gem, capturing Keith as a rap provocateur dismantling the industry’s “fake and plastic” veneer. Released just after his Ultramagnetic MCs-affiliated years, it hints at future personas like Dr. Octagon, blending satire with shock. Its raw energy and bizarre imagery reward fans who crave Keith’s fearless oddity.

For those tracing his roots, this track marks a shift toward the boundary-defying weirdness that defines his legacy, delivered with Bronx grit and a twisted grin. It’s a concise dose of Keith’s provocative genius, a moment where his pen skewers convention with audacious flair. That “Bizarre” ranks among our favorite Kool Keith tracks might raise concern—its unapologetic deviance and animal-fixated rhymes might suggest we’re too deep in his warped world, a sign we’ve embraced the chaos a bit too eagerly.

4. Plastic World (1997)

“Plastic World” is a scathing detour from the Sex Style’s “pornocore” obsession, unleashing a razor-sharp critique of the music industry’s artificiality. KutMasta Kurt’s production—a relentless snare-and-piano combo with a funky, minimalist groove—sets a stark stage for Keith’s venomous flow. He dismantles “clone” rappers and their “perpetrate mobster crap,” spitting lines like, “A million rappers, some clones trying to sound like me / Biting my space styles, biting my horror-core.” His delivery, a mix of disdain and razor wit, slices through the façade of urban beats and payola scams, exposing a city “buried in dreams” of plastic illusions. Unlike the perverse swagger of “Sex Style,” this track channels Keith’s Ultramagnetic MCs roots, grounding his eccentricity in biting social commentary.

Less celebrated than Dr. Octagonecologyst’s sci-fi epics, “Plastic World” is one of our favorites for its unapologetic honesty. Kurt’s sparse beats amplify Keith’s lyrical precision, creating a raw, hypnotic indictment of a homogenized rap scene. The track’s gritty realism, a bold pivot from Sex Style’s taboo themes, showcases Keith’s versatility, blending humor with a middle finger to industry fakes. Its vivid imagery—graffiti playgrounds, wack DJ mixtapes—paints a disillusioned New York, making it a standout in Keith’s catalog and a testament to his refusal to conform.

3. Girl Let Me Touch You (as Dr Octagon) (1996)

“Girl Let Me Touch You,” from Dr. Octagonecologyst, leans into the perverse side of his Dr. Octagon persona, a time-traveling gynecologist with a sinister edge. Dan the Automator’s production—sultry piano keys, smooth bass, and a soulful bop—creates a deceptively seductive vibe, contrasting the unsettling lyrics. Keith’s delivery, sly and leering, drips with crude innuendo as he coaxes, “Girl, what’s wrong? Come here let me take a look,” weaving medical metaphors with graphic lust. DJ Q-Bert’s subtle scratches add a gritty texture, grounding the track’s eerie charm. Unlike the cinematic sprawl of “Blue Flowers,” this song is more direct, its vulgarity tempered by Keith’s playful absurdity, foreshadowing the “pornocore” of Sex Style.

Though not as celebrated as other Dr. Octagonecologyst tracks, it’s one of our favorites for its bold, creepy catchiness. The hook, both infectious and unnerving, captures Keith’s knack for blending humor with discomfort. This track’s raw, provocative energy, paired with Dan the Automator’s sleek beats, makes it a standout in Keith’s warped universe, proof of his fearless dive into Hip Hop’s fringes.

2. I Run Rap (as Dr Dooom) (1999)

“I Run Rap,” from First Come, First Served as Dr. Dooom, is a ferocious declaration of dominance, dripping with venom and dark humor. KutMasta Kurt’s production—grimy snares, skeletal bass, and eerie loops—builds a menacing vibe, echoing the raw edge of Keith’s Ultramagnetic MCs days. As Dr. Dooom, fresh from solitary, Keith unleashes a torrent of vicious disses, targeting “fake” rappers with perverse, razor-sharp metaphors: “Rappers with panty-liners, rent cars, with no recliners.” His flow, a hypnotic blend of controlled rage and unhinged wit, paints him as rap’s ruthless overlord, mocking MCs relentlessly.

Unlike the horrorcore theatrics of “Apartment 223,” this track grounds its chaos in street-level bravado, reviving Keith’s late-’80s topical sting. A gritty standout, “I Run Rap” captures Keith’s rejection of industry gloss, channeling his Dr. Dooom persona’s malevolence with unrelenting force. Its biting satire and unapologetic swagger make it a gem, and one of our favorite Kool Keith joints, another one with a hook that’ll stick in your head for days.

1. Earth People (as Dr Octagon) (1996)

“Earth People” thrusts listeners into the chaotic orbit of his Dr. Octagon persona, an alien surgeon with a penchant for the absurd. Dan the Automator’s production—moody synths, crisp drums, and orgasmic key flourishes—builds a shadowy, proto-trap soundscape that feels like a transmission from Jupiter. Keith’s flow is a wild, unpredictable surge, weaving sci-fi gibberish with dark humor: “Supersonic bionic robot voodoo power / Equator ex my chance to flex skills on Ampex / With power meters and heaters gauge anti-freeze / Octagon oxygen aluminum intoxicants.” These lines, dense with bizarre references, defy logic yet feel oddly cohesive, each verse a disorienting leap. DJ Q-Bert’s frenetic scratches deepen the track’s unhinged vibe, tying the chaos together.

Less celebrated than “Blue Flowers,” “Earth People” is our favorite for its raw, experimental daring. Its shifting rhythms and layered production reject ‘90s commercial sheen, embracing a nerdy, horror-tinged vision. Keith and Dan the Automator make the outlandish plausible, crafting a sonic fever dream that challenges listeners to keep pace. This track’s relentless oddity, a bold middle finger to convention, cements its place as a pivotal moment in underground Hip Hop, demonstrating Keith’s genius for turning absurdity into art.