Digital Underground's leader and mainstay was Greg "Shock G" Jacobs; Shock G formed the group in 1987 with Jimi "Chopmaster J" Dright of Berkeley, California, and Tampa hip-hop radio deejay Kenneth "Kenny-K" Waters.
Heavily influenced by the various funk bands of the 1970s, Digital Underground sampled such music frequently, which became a defining element of West Coast rap. As "Rackadelic", Jacobs designed album covers and cartoon-laced liner notes, in homage to Parliament-Funkadelic album designs. Digital Underground is also notable for launching the career of member Tupac Shakur, as well as spinning off side projects and solo acts including Raw Fusion, Saafir, and singer Mystic.
Following the release of their "Doowutchyalike" single and video in the summer of 1989, the band gained popularity with their song "The Humpty Dance" in 1990. Digital Underground toured nearly every year up until 2008; this consisted of live shows in Europe, Japan, Canada, Australia, and the U.S.
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