L.A. rapper Drakeo the Ruler is a man in demand


It’s a dreary weekend afternoon in midwinter, just three weeks after Drakeo the Ruler swapped the county blues of downtown’s Men’s Central Jail for stacks of blue-striped Benjamin Franklins.

In the brief span since regaining his freedom, the 24-year-old christened Darrell Caldwell has already recorded and released a 16-song mix-tape, “Cold Devil,” with more than 7.5-million SoundCloud listens, headlined a sold-out show at the Observatory in Orange County and been hailed as the most original West Coast stylist in decades — that is if one can unravel his absurdly singular slanguage, cadences and cosmology.

The 11-month iron vacation for multiple counts of unlawful possession of firearms by a felon temporarily halted Drakeo’s coronation, and yet it also gilded his legend. It didn’t hurt that he smuggled a phone into lockup and brazenly flexed on Instagram Live from behind the walls.


“I thought prison would be a little worse,” Drakeo says, slightly smirking as he sips from a Styrofoam double cup. “It was just like boot camp in there, y’know?”

Major labels are frantically bidding to sign him. Pitchfork recently raved about his “mixture of [L.A.’s] street-rap traditions and … colorful fringe elements [that] makes for a strange, irresistible alchemy.” One of the Migos hit him up on Facetime and Lil Yachty remixed Drakeo’s underground hit, “Flu Flamming.”

His ascent arrives concurrently with a previous generation of L.A. rappers, led by Kendrick Lamar and Tyler, the Creator, becoming commercial behemoths, Grammy fixtures, and top-billed performers at Coachella. And yet over the last two years, Drakeo may be the most imitated local rapper, so impactful that’s there’s an entire subgenre of sub-Drakeos, many racking up hundreds of thousands of streams.

Not since Ghostface Killah or E-40 has a rapper invented such a cryptic and psychedelic idiolect. “Uchies” means money. The extended clips on his rifle are “Pippi Longstockings” or “Shenaynays” (named after the character on “Martin” who wore long extensions).

I know how to code everything and I switch it up every time I get bored. People think I just make up words, but everything means something.

— Drakeo


“I know how to code everything and I switch it up every time I get bored,” Drakeo says. “People think I just make up words, but everything means something.”

The phrase, “Mei Ling took me shopping,” is Drakeo’s way of describing breaking into an Asian woman’s house, robbing it, and buying out Neiman Marcus. On “Cold Devil,” there’s an entire song dedicated to taunting his rivals over how no one even knows them at the aforementioned Beverly Hills department store.

The sui generis extends from flow to handshake. Drakeo and his crew, the Stinc Team, don’t grip palms, exchange pounds, or give hugs. They link pinkies to greet. Even his name, which most interpret as a riff on Drake or the Draco AK-47 semiautomatic pistol, actually takes lineage from Draco, the famously harsh lawgiver of ancient Greece who inspired the adjective, “Draconian.”

“There’s something very native to South-Central about Drakeo. Every time he goes against the grain he wins,” says his manager, TK Kimbro. “If everyone is melody rapping, he’ll do the opposite. He’s the most singular rapper to come out of L.A. since Snoop Dogg. A true natural — everything comes to him with ease.”

If Drakeo floats at the vanguard of young L.A. street rap, he’s emerged alongside several highly gifted talents and collaborators who have helped make this a citywide rap renaissance. There’s 03 Greedo from Watts, who describes his sound as “emo music for gangbangers … pain music that’s popping.” A mix-tape with Drakeo is forthcoming, and nationwide adulation seems inevitable provided Greedo can beat the drug-trafficking charges he faces in Amarillo, Texas.

There’s Shoreline Mafia, the lawless East Hollywood crew of skaters, graffiti writers and smokers — reminiscent of a young Odd Future if they were too apathetic to show up to school to burn it down. South-Central’s G Perico exists as a rightful heir to the legacies of Eazy E and DJ Quik. While Drakeo’s own Stinc Team features breakout talents in Ralfy the Plug, Ketchy the Great, and Bambino.


“The great moments of L.A. rap are historically so great that it’s so hard to imagine putting someone in the same category as the ’90s legends,” says Adam Grandmaison, the host of the popular No Jumper podcast, which has championed these artists over the last year.

“Kendrick and [Top Dawg Entertainment] exist in a similar but different dimension; this really feels like the first time in years that we’ve seen an entire class of artists who seem so fresh and new, simultaneously rooted in a West Coast tradition but creating an entirely original one,” Grandmaison continues. “They’re uncompromising and not trying to make hits. And the drama surrounding Drakeo and Greedo’s open court cases has only increased their popularity.”

If the boundaries between traditional gangsta rap, trap, and high-couture luxury hip-hop have become increasingly blurred, Drakeo incorporates elements of each but belongs to no party.

Coining the phrase “nervous music,” Drakeo’s songs are sinister and dense, cryptic and dark, versatile enough to set off a party or shoot it up. His cadences run counterclockwise to the drums, somehow both herky-jerky like a stickshift and swift and smooth like a luxury sports car it controls.

[People] want to kill me. I can’t be driving around in $100,000 cars on the run, listening to soft-ass [music]

— Drakeo

“I live a nervous life. I gotta look around and watch my back from police and these other [people] out here,” Drakeo says. He doesn’t smoke weed, but his celebrated combination of tobacco and codeine suggests self-medication for the stresses of past and present. “[People] want to kill me. I can’t be driving around in $100,000 cars on the run, listening to soft-ass [music].”

He embodies William Blake’s axiom of creating a system or risk being enslaved by another man’s, right down to his jewelry.

His Nikes are fresh-out-the-box red. His lineup is cut cleanly with undulating waves carved into the side of his head. Back covered by a custom-made “Drakeo” jacket. Ears, wrists and sternum blinding with enough diamonds to rival any Rodeo Drive jewelry bazaar.

While it’s rare that a few minutes elapse without Drakeo invoking the phrase, “it’s regular,” what’s regular for him is iconoclastic for everyone else. It’s a rare originality with no obvious wellspring. If one can clearly trace the influences of superstars like Kendrick Lamar, Kanye West and Drake from the synaptic connections of past genius, Drakeo is Athena springing fully formed out of Zeus’ skull, fully armored and ready for war.

If his creative gifts seem divinely ordained, his life’s circumstances have been chaotic. Raised deep in the Hundreds section of South-Central, Drakeo’s mother taught preschool and he barely knew his father. First arrested at 12, stints at youth correctional facilities followed, usually related to criminal charges of burglary or gun possession.

Throughout his adolescence, the ex-Washington High student rarely made it three months at school without getting kicked out. He was more interested in home invasions, or to invoke his coded vernacular, “flu flamming.”


Rapping wasn’t a calling but a way to make legal money and stay out of jail. Averse to the strip-club-ready ratchet phenomenon then sweeping the city, Drakeo recorded a half-dozen unheard mix-tapes where he rhymed freestyled verses over generic trap and Three Six Mafia-type beats. His epiphany came after his brother, who raps as Ralfy the Plug, told him that he needed to start altering the tone of L.A. party bangers to fit their anxiety-riddled, criminology lifestyle.

“I said Imma make it different,” Drakeo says, puffing on a Newport. “We not finna be talking about no ratchet [stuff] … shaking ass. Nah, we gonna’ talk about this money, we not finna be fabricating nothing”

It paradoxically attracted the attention of ratchet’s sonic architect, DJ Mustard, who gave Drakeo a chain and remixed his buzzing “Mr. Get Dough” (adding his own artists, RJ and Choice in the process).

Premiered on WorldStarHipHop in April 2015, it became an underground smash (4.4-million YouTube views and counting) that established Drakeo as an ascendant L.A. talent. Before falling out with Mustard shortly thereafter, the hitmaker hosted Drakeo’s official debut, “I Am Mr. Mosely,” released in October of that year. It was the only signal boost he’d need.

By the top of 2017, when LAPD raided the condo near LAX where Drakeo and the Stinc Team shot their videos, Drakeo’s regional clout was already formidable. The police search and seizure yielded multiple guns allegedly belonging to Drakeo and caused him to spend most of last year behind bars, but it ultimately enhanced his outlaw stature and popularity.

Exactly two weeks after the interview, Drakeo was arrested again, this time near a liquor store on 108th Street and Western Avenue for possession of a firearm (Drakeo has steadfastly denied the handgun belonged to him). He was booked at the 77thSt. Division of the LAPD — where Drakeo claims that the officers were playing his music, leading him to believe that he’s being targeted.


At this moment, Drakeo occupies a cell in the Men’s Central Jail, the same place where he spent most of last year. The principal difference being that this time as he reentered the prison, most of the inmates welcomed him as a returning conqueror, aware that his fame had grown exponentially during his short bout of freedom.. When he calls from jail, he’s surprisingly Zen.

“They got it out for me, but it’s all right, I’m chilling where I’m at,” Drakeo says. Barring any unforeseen changes, he’s slated for a March 30 release. “I’m kind of mad, but there’s only so much that I can do. It’s bad that I’m in jail, but it could be way worse.”

Most days have been spent making phone calls to friends and management. He mentions how quiet it is in there in passing, but it almost seems like he’s savoring it, knowing how loud things will be when he gets out — this time, hopefully for good.

“I’m going to hit the studio first, then sign a deal, move out from my mom’s place and up out the hood,” he says, laughing, then instinctively shifting back into the invincible tone of his mix-tapes.

“These police can’t stop nothing that I’m doing. Nothing,” he repeats himself, as a robotic prison telephone system vocal reminds everyone on the phone that this call is being recorded. “All this … this is just going to make it better for me when I get home.”