Born Derrick Dewayne Hill and raised in the rough Dixie Homes area of North Memphis by his grandfather, Kingpin Skinny Pimp began rapping in 1985 while attending Herman Junior High School. Several years later, he began making waves throughout the Memphis region - first alongside DJ Squeeky and his crew, then alongside the rival Three 6 Mafia camp after defecting.
Throughout the early '90s, the Memphis underground peddled mix tapes, but that changed in 1995 when Three 6 Mafia formed its own record label, Prophet Entertainment, and issued its debut album, Mystic Stylez, on which Skinny Pimp performed. A year later he made his own album debut, King Of Da Playaz Ball, which DJ Paul and Juicy J of Three 6 Mafia produced and released on Prophet Entertainment.
That same year, Basix Records released Skinny But Dangerous, a collection of his older underground recordings also produced by DJ Paul and Juicy J. Skinny Pimp's partnership with Three 6 Mafia didn't last long, and he was soon out on his own while his former affiliates went on to substantial underground success. Regardless, Skinny Pimp stayed on the grind and kept recording one album after another throughout the remainder of the decade and into the next.