drummer and later taught himself to play piano, but in the late ‘70s he became fascinated with the burgeoning hip-hop art form and began experimenting with turntables while living in Queens. After a move to Tampa while still in his teens, he formed a mobile DJ crew called the Master Blasters and became an on-air personality for WTMP, although he was later fired by that R&B radio station for playing the 15-minute version of Funkadelic’s “(Not Just) Knee Deep.” Jacobs, who had dropped out of high school while living in Florida, eventually resumed his education and met a musician named Kenneth “Kenny-K” Waters while attending Hillsborough Community College. The two started collaborating, and after another move to Oakland, Calif., they formed Digital Underground with Jimi “Chopmaster J” Dright in 1987.
Digital Underground’s first single, “Underwater Rimes,” topped the pop chart in the Netherlands in 1988; the group signed to Tommy Boy Records a year later and scored a respectable U.S. hit with “Doowutchyalike,” which went to No. 29 on the Billboard Hot R&B Singles chart and No. 19 Hot Rap Singles chart despite getting almost no radio airplay. That single did receive support from MTV, placing 40th on the cable network’s top 100 music videos of 1989 list, but it was another single from the group’s 1990 debut album, Sex Packets, that established them as platinum-selling sensations.
Nzazi Malonga, a longtime friend who served as head of security and helped manage the group, said Jacobs had lived with him in the Los Angeles area for several years to get sober in the early 2000s, but had relapsed and been recently living with family in Florida. He gave away much of his wealth and worked on many unfinished side projects, struggling to find validation from those around him.
“He had hundreds of things he could create. He could draw, he could write music, play piano, he could score things, he could write stories and scripts,” Malonga said. “But unless someone was telling him he was OK, he would never present that.”
So how did the Humpty Hump thing start?
“George Clinton used to use his anonymousness to keep paparazzi and record company people off of him when he didn’t want to answer to them. People used to wonder like, ‘Which one is George Clinton? He’s either Starchild or Sir Nose…’ You never really got a good look at him. So I had that game as well. I was really entertained by Andy Kaufman having two or three characters too; I always thought that was funny. My mom used to tell me about all the Saturday Night Live cast, how they would fool the [company] president and sometimes come in dressed a certain way to scare NBC. I liked the practical joke thing. I didn’t plan it. I get a lot of credit; people are like, ‘Shock is genius—he got Humpty for this, and Shock G for the…’ But it just evolved.
“There was a point when the whole group was like, ‘Wait, wait, wait—you don’t look all the way Humpty yet—let me see—the pants! The pants ain’t Humpty. Better pants, better pants. Yeah, all right. I think he should go in with two girls, you need another girl.'”
“It was so fun to do that I just would do it. Not so much for business purposes, and not so much for artistic purposes, but it was just so much fun. It was like having the Joker in my pocket.”