The group's first album on Tommy Boy was 1989's "Sex Packets". Album singles "Doowhutchyalike" and especially "The Humpty Dance" both showcased Shock G's nasally prolific and lewdly humorous alter ego Humpty Hump. The character was a hit as the single went to No. 11 on the pop charts, pushing the album to platinum sales. "Sex Packets" was followed by "This Is An EP Release" in 1991, featuring two songs used in the bizarre dark comedy "Nothing But Trouble" ("Same Song" and "Tie The Knot", both of which were "performed" by the group in the film, as well). The EP was Digital Underground's first recording with new member Tupac Shakur and the group Gold Money; it went gold, as did the subsequent full length album "Sons Of The P", released that same year, with hit singles "Kiss You Back" and "No Nose Job".
However, as the '90s wore on, the rap charts were taken over by hardcore gangsta artists, and more lighthearted and off-kilter music like that of Digital Underground was no longer as commercially viable as it had been just a few years prior. Despite debuting another successful solo rapper, Saafir, 1993's "The Body-Hat Syndrome" barely registered on the charts, and the group disappeared for three years before releasing "Future Rhythm" in 1996 and "Who's Got the Gravy?" in 1998.