One of indie rap's most prolific and profoundly bugged-out artists, Kool Keith puts out albums with uncommercial, pointedly abstract original music with no samples, almost always creating an entirely new persona for himself from disc to disc. The MC born Keith Thornton came up as part of the Bronx crew Ultramagnetic MC's, the oddball star of their 1988 cult classic Critical Beatdown. He appeared on the cover of that album wearing a Budweiser painter's cap sideways while claiming "I swarm around with a thousand bees/Absorb earth and the honey from trees."

After some rocky years during which Keith spent time institutionalized in New York's Bellevue psychiatric hospital and the Ultramagnetic MC's released their excellent, but commercially unsuccessful second album, 1993's The Four Horsemen, Keith released his first notable solo single, "Earth People," in 1995, recorded under the name Dr. Octagon. Released by San Francisco–based Bulk Recordings, the record sent shock waves through the hip-hop independent-label underground, setting the stage for the Dr. Octagonecologyst. album, a slab of mondo bizzaro brilliance. With Dan the Automator making beats and DJ Q-Bert's sick scratching, Dr. Octagon was totally unlike anything else and totally right, sending kids, heads, and critics around dazed singing Twilight Zone–like tracks "Blue Flowers" and "Halfsharkalli-gotarhalfman," which drew equally from pulp science fiction and the darker reaches of Keith's noggin. He quickly followed with Sex Style, posing lasciviously on the cover in tight pink underwear. Kool Keith's other main mode is dissing other rappers and the record industry. Robbie Analog was an entire album swiping at the RZA's Bobby Digital identity; Kool Keith has also taken down OutKast's Andre 3000 for wearing wigs long after Keith went around wearing a rubber Elvis wig for all of 1999. As Keith succinctly put it: "Rappers take it personal/you're wack." On First Come, First Served Keith dished up "hamburgers infested with mice" and delivers the battle track "You Live at Home With Your Mom." In 1998 Keith teamed up with Tim Dogg as Ultra for the My Turn Records 12-inch "The Industry Is Wack." The uncompromising hardcore classic finds Keith claim-ing he "can't trust Little Richard -- Little Bitchard" and utilizes enjambment rhyme on the line "girls today slept with Rock Hudson/the NBA, your favorite ballplayer turned gay."

Under the guise of Dr. Doom, Keith even "killed off" the popular Dr. Octagon on record. Notably, Keith teamed up with Ice-T as the Analog Brothers for Pimp to Eat with "Bionic Oldsmobile" and "Permsbaldheadsafrosdreads," making the album another must of odd excellence. Thee Undatakerz features morgue stories from Keith's new persona Reverand [sic] Tom. Also worth hearing is Keith's freestyle insect rap on Jurassic 5's Power in Numbers -- as usual, Keith is dangerously ill.