Pepperboy and the Extremely Difficult Way

Pepperboy and the Extremely Difficult Way

You’ll hear him say it in every album he releases. And he’ll say “the super hard way” every few turns of the conversation, seemingly without realizing how often he says it. It’s a convenient catch-all phrase for the long and perilous road he’s been on since 1993. But if anyone has earned the right to discuss the extremely difficult way, it’s Pepperboy.

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

He’s alive to witness all of this because of some combination of rehabilitation, ambition, dumb luck, or something in between.

“For example, when I was 13, I lost my first homeboy.” Man, you messed me up. You’re young, and all you can think about is vengeance and shit. You’re a kid, and you see your homeboy get killed. “The streets just took me, man.”

Pepperboy, born Jerry Davie, spent his entire adolescence contributing to Little Rock’s “Bangin’ in the Rock”-era crime rate. It wasn’t until he was in prison, serving 30 months of a 10-year sentence in the Varner Unit for “possession with intent and a firearm: just protection,” that he realized he could turn his street stories into music.

Following his release from SuperMax, he released his first album, “Str8 Off tha Block, Pt. 1,” in 2002, followed by a steady stream of mixtapes. Pepperboy gradually evolved into a distinct voice from Little Rock’s south side with each new release, moving away from boilerplate, do-it-yourself gangster rap trappings.

Pepperboy’s gritty, sonically unique take on rap music wasn’t exactly setting Little Rock on fire, despite the fact that he was carrying a lot of respect in the streets following his prison stint. But those who received it got it.

“It all began with ‘Blame tha Block.'” “At first, it was a little amusing to me,” said 607, one of Pepperboy’s most vociferous supporters. “Because it wasn’t the conventional beat selection or nothing, folks were trying to tune their ears.” Some people felt it, while others did not. He has this crazy voice, and the message was there for those who have been [in the streets]. It’s a very genuine message he’s conveying.”

Between the obligatory minor-key G-funk tracks (“Block Bleedin”) and synth-y odes to weed-smoking (“Smoke Smoke Smoke”), 2003’s “Blame tha Block” mixtape revealed the first signs of the positive street wisdom and plain-spoken pleas for peace that would define an older, more earnest Pepperboy years later. The proof was in the production if the message wasn’t fully baked into the lyrics.

The title track, an infectious party record built on robotic squeaks and pawn shop drum machines, featured an unlikely collaboration with Major League’s Boogie Shoez.

“We were in opposing gangs,” Pepperboy explained. “There was no war at the time, but we had warred and shit.” I saw him in the club one night and texted him, saying, ‘Boogie, mane, let’s do a record.’ Let’s get this nonsense straightened out.’ It was strange because he was so high up in his gang.”

The two drove Pepperboy’s ’97 Cadillac Sedan Deville to Pine Bluff’s DTO Studios and returned 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 from Boogie Shoez.

Following the success of “Blame the Block,” Pepperboy released at least one full-length album per year, in addition to singles and EPs, all of which featured original beats by local producers. But he wasn’t having the success he desired and admits to wanting to hang up his microphone.

Related: Who Was The SNL pepperboy?

Pepperboy drew on his prison experiences to create “One Moe Night,” a concept album filled with keen-eyed, literary observations from behind bars, in 2010.

Andrew Noz, the omnipresent music writer, NPR rap critic, and workhorse blogger, noticed the video for that album’s first single, “Tha Parts,” in March 2011.

“Tha Parts” quickly caught 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 Thomas Pynchon was quick to sign on, rapping over the LP-produced beat from “Tha Parts” on “My Life,” a standout track from Lil B’s satirical “Bitch Mob: Respect Da Bitch, Vol. 1.”

Pepperboy changed his style after discovering a new, Internet-centric sub-genre of rap and abandoning his strict (“stubborn,” he says) adherence to using locally-sourced beats.

“I’ve been underground a lot. “I was just in my own little world, so I had no idea what ‘cloud rap’ was.”

That cloud rap sound is a radical departure from the standard hip-hop formula — certainly from the formula to which Pepperboy had grown accustomed. It’s more Brian Eno than Dr. Dre, with production that foregoes percussion and typical beats in favor of abstracted, ambient soundscapes. It’s also a young man’s genre, and you wouldn’t expect to find a No Limit-inspired Southern rapper there.

However, 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 liking to Pepperboy’s eccentric positivity and folksy, O.G. demeanor.

His current track, “Felon,” became his most successful tune to date this summer. Pepperboy raps on being ashamed of his criminal background while offering a litany of simple virtues akin to a street-smart “Poor Richard’s Almanack” to a lovely, vocoder-breathed beat from Blue Sky Black Death.

He’s noticeably relieved after a decade of hustling music when he declares, “I’ve done found my style now.” It’s just the sound I was searching for. I don’t think of myself as a hardcore rapper. I’m not a gangsta rapper in the least. I’m a life-affirming rapper. I don’t want to shoot you for a record. I’d like to state unequivocally that you should put down your gun.”

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