Digital Underground was founded in Oakland in 1987 by Gregory “Shock G” Jacobs together with Kenneth “Kenny-K” Waters and Jimi “Chopmaster J” Dright. The group blended rap with the funk of George Clinton and Parliament, with humour, costumes and a rotating cast of alter egos. From 1989 their records came out on Tommy Boy Records, starting with the single Doowutchyalike; in 1990 The Humpty Dance, from the album Sex Packets, became a nationwide hit.
How Tupac joined
Tupac’s manager at the time, Leila Steinberg, introduced him to Atron Gregory, Digital Underground’s manager. In spring 1990 Tupac went on his first tour with the group, on the road with Big Daddy Kane, Heavy D and MC Lyte, as a roadie, dancer and hype man. By his own account, Atron Gregory had first signed Tupac’s group Strictly Dope, not Tupac alone. Life on the road was a tough school: he saw how a successful band worked and learned the stage before he got his own microphone.
It is often said that Tupac “officially” became a member on August 2, 1989, and was already one of seven members when the group signed with Tommy Boy. Neither could be confirmed: the Tommy Boy deal predates Tupac, and what is documented is that he came aboard in 1990.
“Same Song”
On January 15, 1991, the EP This Is an EP Release came out; it went gold as early as March 1991. Two of its songs were used in the film Nothing But Trouble with Dan Aykroyd and Chevy Chase, among them Same Song. This is where Tupac raps his first verse on record; in the video he plays an African king carried in a litter. The group also makes a brief appearance in the film, Tupac included.
Also in 1991, Tupac appeared on Digital Underground’s album Sons of the P (The DFLO Shuttle). His last appearance with the group came in 1993, in the song and video Wussup Wit the Luv, a track against racism.
Still family
The bond stayed close after Tupac went solo. Shock G co-produced 2Pacalypse Now (1991) and in 1993 produced I Get Around, on which he and Money-B rap and appear in the video. Money-B also rapped with Tupac on Above the Law’s Call It What U Want. The Digital Underground circle also gave rise to the Underground Railroad collective, with which Tupac recorded his first solo album.
Shock G died on April 22, 2021, aged 57. The group appears in documentaries about Tupac such as Tupac: Resurrection (2003).