After relocating to Oakland, California, Shock G formed Digital Underground along with Chopmaster J, and Kenneth Waters (also known as Kenny-K. After around 15 months of unsuccessful negotiations with various small record companies, in 1988 the trio 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 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 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.