Shock G Revolutionized Hip-Hop — and Created a Secret Trove of Funky Art

Editor’s note: This story is part of That’s My Word, KQED’s year-long exploration of Bay Area hip-hop history.

For many listeners, Bay Area rap from the late ’80s and early ’90s calls to mind the dark synths and trunk-blapping bass of mobb music. The popular Northern California subgenre was born out of poverty-induced turf conflicts and dreams of riches, producing timeless classics like Too Short’s Born to Mack and E-40’s Federal. Though nuanced and laced with hood wisdom, much of hip-hop from that period focused on pimping, hustling and territorial claims.

It’s groundbreaking, then, that during the same time, an aberrant, free-spirited rapper from the East Coast would arrive in Oakland and forever change the rap scene with his boundless expressions of joy. 

This Afrosurrealist galaxy traveler with a microphone and a Sharpie? Gregory Jacobs — better known as Digital Underground frontman Shock G, or his alter ego, Humpty Hump. His platinum-selling rap collective gave Tupac Shakur his start and made classic hits like “The Humpty Dance,” “Kiss You Back” and “Freaks of the Industry.” His place in Bay Area rap’s Hall of Game is unquestionable.

Yet, there’s another dimension to Shock G — who passed away in 2021 at 57 years old — that doesn’t often get the same adoration as his music. In addition to his prowess as a lyricist, producer and pianist, Shock G was an accomplished visual artist who created enough work to fill a museum.

The majority of Digital Underground’s projects involve Shock G’s visual contributions in some form — whether through photo collages or hand-drawn illustrations credited to an alias. And many more of his drawings and low-brow doodles still exist in privately stored boxes and notebooks, in the care of his friends and family. 

A descendant of Parliament-Funkadelic’s unconventional sensibilities, Shock G was among the earliest key figures who gave Bay Area rap its humor and its distinctive weirdness. And he paved the way for multi-hyphenated rap experimentalists like Tyler, the Creator, Tierra Whack and Lil B to thrive in generations that followed.

“It makes it easier when someone comes with the full package: producer, writer, artist, storyboards,” says Atron Gregory, Shock G’s friend and Tupac’s former manager. “He could give you everything. That’s pretty rare. Very rare at that time. Now there’s more people who do it.” 

The origins of an experimental artist

Born in New York City and later raised in Tampa, Florida, Shock G grew up drawing, reading comic books and attending comic conventions from an early age. Gregory says that Shock G’s mother, Shirley Kraft, always encouraged her son’s gifts for visual art.  

“There was never any pushback against it,” he tells me over Zoom.

As an adolescent, Shock G’s multifaceted creativity was evident. He was awarded “Most Talented” for his drumming abilities in junior high, and eventually began spinning records in the early ’80s. By age 16, he DJed regularly on the air under the name Gregory Racker and formed the Tampa group the Master Blasters. Through it all, he incessantly sketched his thoughts as visual freestyles.

“When we were in New York as kids, we used to draw our own comic books,” says Kent Racker, Shock’s younger brother, who lives in the Bay Area. “When we were in Tampa, he almost got a syndicated comic strip out called Looney Dap. It was about this kid getting in trouble and doing weird stuff. That almost got published.”

Shock G and his family eventually moved to the East Bay, where he would make a name for himself after forming Digital Underground in 1987 with Chopmaster J and Kenny K. (The collective’s membership changed with every album, but Shock G remained a constant.) 

Upon meeting Shock for the first time, it was obvious to Money B — DU’s co-lead MC and Shock’s longtime ride-or-die — that Shock was creating his own wave.

“I realized he was an artist from day one,” remembers Money B. The two ran in similar circles: In 1988, Shock G was promoting an early Digital Underground single, “Underwater Rimes,” and Money was performing at the same East Bay clubs with future DU member DJ Fuze. Right away, Money says, Shock stood out: “He was wearing a beret and these sweatpants with something drawn on them. He wore tassels.” 

Money B was instantly fascinated. “Underwater Rimes” featured Shock G blissfully rhyming as “a deep-sea gangster, underwater prankster” over aquatic sound effects, and his artwork for it featured sea creatures in hip-hop clothes, talking slick. Fittingly, the surrealist track came out with “Your Life’s a Cartoon” as the B-side. 

“You could tell he had an originality about himself,” Money B says. 

Shock G’s expansive visual style

Shock G’s raunchy humor was on full display on Digital Underground’s canonical 1990 album Sex Packets, which sold over a million copies. And it extended to his visual art from that period, too. He even designed condom wrappers that Tommy Boy Records gave away to promote the record.

“A pamphlet went out to San Francisco strip clubs and peep shows,” Money B recalls. “He drew the invitation to the original [album release] party. Everything had art attached to it.”

Shock’s avant-garde approach was also evident on stage. For each show, he would custom-paint a plastic nose for his Humpty Hump getup and give it away to a fan at the end of the night. His quirky, exuberant fashion and alter egos were also a precursor to the far-fetched costumery that would later define beloved Bay Area rappers like Mac Dre, who during the hyphy movement dressed up as a genie, a fictional president and a tennis pro.

This kind of rebellious, form-bending aesthetic evolved throughout Shock G’s career. For 1991’s This Is an E.P. Release, he provided a “Customer I.Q. Quiz” in the top corner of the album cover. Answers for a multiple-choice question about what “E.P.” means included “EXTRA POOR,” “EXTENDED PHILOSOPHY,” and “ERECT P_NIS.” Later, in the early aughts, Shock introduced an illustration series called Assholes that starred fictional characters based on anuses (yes, actual assholes).

No matter the subject, though, Shock’s illustrations linked him to an Afrosurrealist, funky artistic lineage that went back decades. At various points in his life, he openly credited Parliament-Funkadelic’s album cover artist Pedro Bell, whose strangely cosmic, erotic illustrations were a major inspiration of his.

“Part of my huge affection for P-Funk is the humor. It’s not so militant,” Shock said on the Netflix series Hip-Hop Evolution. “It’s just like… ‘Dance your way out of your constrictions.’”

Shock G never actively promoted his artwork, instead lasering in on his rap ambitions. But along with Del the Funky Homosapien, who also has a background in visual art, Shock was part of the first wave of Bay Area rappers who helped to define what it meant to be a weird, versatile, poly-skilled artist. 

“In the late ’80s, there were maybe three people doing art like him,” Gregory says. “He wanted to be accepted as a rapper. That’s why you’ll see [his art is signed with aliases] Rackadelic and Staying Busy Productions [instead of Shock G]. He separated all that to make sure he was accepted as a rapper and had success there.”

Tupac’s caricature in This Is an E.P. Release

As Digital Underground’s heartbeat, Shock G put his playful touch on everything — and often communicated through exaggerated drawings rather than words.

“He wasn’t drawing pictures that were realistic. He would accentuate your main features. Huge freckles, big lips,” Money B says. “[He drew] Tupac’s big ol’ nose and rigid cheekbone. Some people took offense to how they were drawn, but they didn’t get it. [If] he didn’t like you, he might draw some crazy pictures.”

A perennial jokester, Shock’s cartoonish ways weren’t used solely for mockery; they could also serve as a language for love, unity and representation. Perhaps no other Digital Underground project displays this more poetically than the gold-certified This Is an E.P. Release, which features the single “Same Song” — famous for being Tupac’s first published track. 

Tupac began his journey with Digital Underground in 1989 when he signed to their underground label, TNT Records. It’s likely that without Shock G’s clairvoyance, the version of Tupac we know today may not have arrived as quickly as he did — or, at the very least, the future icon wouldn’t have been given such a momentous debut opportunity in front of a national audience.

Shock and Tupac’s friendship is forever illustrated on This Is an E.P. Release. The cover features Shock’s hand-drawn portrait of the entire DU squad, himself included, with one arm lovingly wrapped around a young Tupac’s shoulders.

In the new Hulu documentary Dear Mama, Tupac praises Shock G for giving him his earliest validation as a rap artist: “Shock G made sure people saw me as a member of the group. And because he did that, it gave me the courage and the confidence to really just do what I wanted. That’s the best thing one human being can do for another.”

Thanks to Shock G, Tupac finally saw himself — literally and figuratively — as a successful musician.

Unseen artwork and Shock G’s final act

There are countless Shock G visuals that the public has never seen: The zany machinations he would invent on the fly while sitting on a tour bus, hanging backstage or out late at night with his crew. 

A napkin at a burger joint was a canvas to be filled with heartfelt messages for his closest kin. A cardboard box at a party, in his hands, could mutate into a comic strip panel for nonsensical humor. The back of a receipt evolved into a map drawn for a friend before a road trip. Even the inside lining of his jackets became surfaces he could stylize, converting them into wearable artwork that he would later give away to fans.

Shock G continued making visual art into his last years, often making custom holiday cards for friends and family members, says his brother, Kent Racker. The MC also experimented with abstract, acrylic canvases after moving to Topanga in Southern California as he grew older. Unfortunately, his artistic evolution was cut short. Shock G died of an accidental drug overdose in Tampa, where he spent the end of his life, on April 22, 2021.

Racker imagines that, had he lived, Shock G could be painting large-scale murals. “But he wasn’t concerned about the promotion of people knowing about [his art while he was alive]. He was just in tune with being able to create a beautiful representation of DU as an artist.” 

Racker’s estimation can’t be far off. In later interviews, Shock G hinted at wanting to try new things.

“I wanna get out there and mix it up a little more,” Shock G told journalist Tamara Palmer in 2011. “I wanna have fun and just make anything. It ain’t gotta be Eddie [Humpty Hump] Humphrey. It ain’t gotta be Shock G.”

Palmer initially met Shock G for an MTV interview in 2004 and kept in touch. She says he ran his own website, Shock-G.com, and would often post “highly illustrated” work, including a comic strip at one point. (The site is still active but became a fan site domain after his passing).

“They were just made-up characters,” says Palmer. “There was no deeper meaning to it, I don’t think. He provided very surprising comic relief.”

Eventually, Palmer witnessed his artistry firsthand at a mutual friend’s house party, where they doodled together for fun. “[The art we made together was] cheeky, super cheeky. I glued a flier to the lower corner of a wooden tray and he turned it into a bar scene with a male fish flirting with the female fish. It was like a big wink,” says Palmer.

Late in his career, along with painting, Shock G veered further into jazz — with Gregory, he recorded a solo jazz piano album, the posthumously released The Piano Man. 

“As an illustrator and piano player, that was unheard of back then,” Gregory adds. “Nowadays, Roddy Rich and Tyler, the Creator, they have these pianos. Shock went to see [Roddy’s] show in 2018, and the manager came up to tell Shock that [Roddy] is the only rapper to play the piano.”

Gregory smirks while sharing this, knowing that Shock mastered the instrument many moons ago. Add to that the immeasurable amounts of unshared, custom artwork in Shock G’s collection, and you have a once-in-a-generation creative mind.

“You gotta think, when we’re touring and on buses, he would draw something every day. Idle time was never idle time [for him]. He was creating something. Even on a napkin or a note, it was artsy,” Money B shares.

Gregory estimates that “95% has probably been unseen.”

All told, Shock G may have been one of the Bay Area’s most prolific, subversive visual artists — a visionary who bent the lines of human geometry with the “Humpty Dance” and on the page with his out-of-this-world drawings. And according to his brother, it couldn’t have happened anywhere except Oakland.

“It would not have happened back East. The style at the time, we always laugh and joke at ourselves about being hippies,” Racker says. “He probably could have come up as a rapper in New York, or anywhere, because of his musicality and being around hip-hop when it was forming. We had that foundation. But coming out to the Bay Area and California, it really amplified and illustrated his aesthetic in the work, and he just kept drawing and creating a visual world.”