Pepperboy at home in Little Rock Brian Chilson

In his music, you’ll hear him say it in every album he drops. And every few turns in conversation, he’s going to say the phrase “the super hard way” seemingly without ever really noticing how often he says it. It’s a convenient catchall to describe the long and profoundly thorny road that he’s been on since 1993. But if anyone’s earned the right to talk about the super hard way, it’s Pepperboy.

Now in his mid-30s, things are finally looking up for the long-overlooked cult rapper’s career, with a single that’s slowly growing viral on YouTube, a few still-fresh endorsements from Spin and The Fader and a rising reputation as the unlikely elder statesman of the emerging “cloud rap” genre.


By some testament to rehabilitation or ambition or sheer dumb luck or something in between all of those, he’s alive to see all of this happening.

“Like, I lost my first homeboy, he was 13. Fucked me up, man. You’re young, all you think about is revenge and shit. I mean, you a kid and you see your homeboy get killed. Streets just kinda took me, man.”


Pepperboy — born Jerry Davie — spent the entirety of his teen-age years doing his share to raise Little Rock’s “Bangin’ in the Rock”-era crime rate. It wasn’t until he went to prison — serving 30 months of a 10-year sentence in the Varner Unit for, he says, “possession with intent and a firearm: just protection” — that he had the idea of turning his stories from the street into music.

After his release from SuperMax, he dropped his first album, “Str8 Off tha Block, Pt. 1,” in 2002, with more mixtapes following at a steady tack. With each new release, Pepperboy moved further away from boilerplate, D.I.Y. gangster rap trappings, gradually evolving into a unique voice from Little Rock’s south side.


Although he was carrying a lot of respect in the streets following his prison time, Pepperboy’s gritty, sonically unfamiliar take on rap music wasn’t exactly setting Little Rock on fire. But the folks who got it, got it.

“It all started with ‘Blame tha Block.’ At first it was a bit funny to me,” said 607, one of Pepperboy’s most vocal champions. “It wasn’t the traditional beat selection or nothing, so people were trying to get their ears adjusted. Some people felt it, some people didn’t. He has this crazy voice and the message was there and people who have been [in the streets] recognize that. It’s a real genuine message that he’s putting across.”

In between the requisite minor-key G-funk tracks (“Block Bleedin”) and synth-y odes to weed-smoking (“Smoke Smoke Smoke”), 2003’s “Blame tha Block” mixtape showed the first signs of the positive street wisdom and plain-stated appeals for peace that would define an older, more earnest Pepperboy years later. If the message wasn’t fully baked in the lyrics, the proof was in the production.

The title track, an infectious party record built on robotic squeaks and pawn shop drum machines, featured an implausible collaboration with Boogie Shoez of essential ’90s Little Rock rap crew, Major League.


“We were in rival gangs,” Pepperboy said. “There wasn’t a war then, but we had warred and shit. One night, I seen him in the club and posted him, like ‘Boogie, mane, let’s do a record. Let’s clear this shit up.’ He was way up high in his gang, so it was kinda weird.”

The two took Pepperboy’s ’97 Cadillac Sedan Deville to DTO Studios in Pine Bluff and came back to Little Rock with a truce between their respective crews and the mixtape’s centerpiece in the can, featuring a wildly catchy, hyper-assonant hook, courtesy of Boogie Shoez.

Following the success of “Blame tha Block,” Pepperboy released at least one full length per year on top of singles and EPs, all exclusively using original beats from local producers. But he still wasn’t seeing the success he wanted and quickly admits to wanting to hang up his mic.

In 2010, Pepperboy drew on his experiences in prison to release “One Moe Night,” a concept album filled with keen-eyed, literary observations from inside the pen.

In March 2011, the video for that album’s first single, “Tha Parts,” caught the attention of Andrew Noz, the omni-present music writer, NPR rap critic and workhorse blogger.

Soon after Noz’s endorsement, “Tha Parts” got the attention of Lil B, a.k.a. the Based God, the endearingly warped rapper sui generis who redefines irreverent, post-modern prolificacy with each multi-hundred track mixtape he drops. The rap game’s equivalent of Thomas Pynchon was quick to co-sign, rapping over the LP-produced beat from “Tha Parts” on “My Life,” a stand-out track from Lil B’s sardonically-titled “Bitch Mob: Respect Da Bitch, Vol. 1.”

“It’s that new Bitch Mob mixtape: Shouts out to Pepperboy in Arkansas, shouts out to Noz, ya’ feel me?”

The national attention was enough to convince Pepperboy to alter his style, dropping his strict (“stubborn,” he says) adherence to using locally-sourced beats after discovering a new, Internet-centric sub-genre of rap.

“I’ve been real underground. I just be in my own little world, so I knew nothing about ‘cloud rap.’ “


That cloud rap sound is a pretty radical departure from the normative hip-hop formula — certainly the formula Pepperboy had grown accustomed to. Distinguished by production that forgoes percussion and typical beats for abstracted, ambient soundscapes, it’s more Brian Eno than Dr. Dre. It’s also a young man’s genre and not a place you’d expect to find a No Limit-inspired Southern rapper.

But the major figures of cloud rap — spiritual guru Lil B, young visionary Squadda Bambino (of Main Attrakionz), and critically-acclaimed producers like Clams Casino and Friendzone — quickly took a shine to Pepperboy’s eccentric positivity and folksy, O.G. disposition.

This summer saw his latest single, “Felon,” become his most successful song to date. Backed by a gorgeous, vocoder-breathed beat from Blue Sky Black Death, Pepperboy, in his light-helium drawl, raps about being ashamed of his criminal past while delivering a litany of simple virtues akin to a street-smart “Poor Richard’s Almanack.”

After hustling music for an entire decade, he’s visibly relieved when he says “I’ve done found my style now. It’s the sound I’d been looking for. I don’t consider myself a hardcore rapper. I’m definitely not no gangster rapper. I’m a positive, life rapper. I don’t wanna get on a record and shoot you. I wanna get on the record and tell you to put the gun down.”