5. Kool Keith
From: Bronx, NY
Signature Song: Ultramagnetic MCs "Kool Keith Housing Things" (1988)
Kool Keith is an interesting case; in the wake of his 1996 album with Dan the Automator, Dr. Octagonecologyst, the rapper became something of a critical favorite. The combination of his disregard for hip-hop conventions, his lyrical eccentricities (see song titles like "Halfsharkalligatorhalfman"), sci-fi obsession ("Earth People") and general prurience ("Girl Let Me Touch You") were the perfect critic's cocktail. The record was a solid one, but the Kool Keith obsession in certain circles was a bit over the top, raising questions about whether that appreciation might be a bit condescending.
There's no denying the fact that Keith remains an incredibly distinctive, clever rapper, one who has long evaded the boxes the industry might try to stick him in. He got his start with the still-underrated Ultramagnetic MCs, arising during one of hip-hop's headiest years, 1988. Going up against a series of indisputable classics, the group's enormously creative debut slipped under the radar of many, but the record's enduring influence helped create a lane for rappers who weren't afraid to be the oddball in the room.