Soon after relocating to Oakland, California, Shock G formed Digital Underground along with Chopmaster J, and the late Kenneth Waters (a.k.a. Kenny-K). After around 15 months of unsuccessful negotiations with various small record companies, in 1988 the trio finally released a 12-inch single on Macola Records. It featured "Your Life's a Cartoon" as the A-side and "Underwater Rimes" as the B-side. Both songs were penned, produced, and performed by Jacobs, who also sketched the cartoonish cover illustrations. The record included the logo for Digital Underground's startup label, TNT, as well as Macola's logo. TNT was also founded by Tupac Shakur's management CEO Atron Gregory. In 1989, the group signed with Tommy Boy Records and released "Doowutchyalike", receiving minimal radio airplay but became an underground hit. Its video was more successful, reaching number 40 on the MTV's top 100 videos of the year. "Doowutchyalike" paved the way for Digital Underground's debut album Sex Packets and the highest-charting song of their career "The Humpty Dance" both released in early 1990, and both achieving platinum sales certifications by the RIAA. The latter was rapped by "Humpty Hump," the most flamboyant of Shock G's several alter egos. By that time, Digital Underground had expanded significantly, with DJ Fuze, Money-B, and Schmoovy-Schmoov joining the group, and with Ramone "Pee Wee" Gooden and Tupac Shakur joining by 1991.
