(1991-1996) Hill was raised in North Memphis' Dixie Homes projects, where he lived with his grandfather. He also hung and stayed at Hurts Village, a neighborhood in North Memphis. He began rapping in 1985 while attending Humes Jr. High School. After graduating, he began making mixtapes with a local DJ from Orange Mound called Squeeky. A few years later, their relationship ended and Skinny Pimp began associating with DJ Paul and Juicy J of the Three 6 Mafia. His long time friend, 2-11, rapped with him very often, also hailing from Hurts Village.

Left because DJ Paul tricked him into signing over his rights to the album King of da Playaz Ball while he was going through a rough patch, Paul gave him $10,000 and told him to "buy a car and put some rims on it"; All the money made from the independent CD sales went to Paul, somewhere in the sum of $400,000.