Influential L.A. rapper Drakeo the Ruler is killed at 28

By August BrownStaff Writer

Dec. 19, 2021 9:44 AM PT

Drakeo the Ruler, whose surrealist slang made him one of the most original stylists in Los Angeles hip-hop, died Sunday morning from injuries after a stabbing at the Once Upon a Time in L.A. festival. He was 28.

A representative for Drakeo confirmed his death to The Times.

Drakeo’s attorney John Hamasaki said in a statement, “We spent the hardest two years together fighting for his freedom, facing life, before walking out a free man just over a year ago. Through it, we became friends and then like family. I don’t even know how to start processing this.”

The rapper, born Darrell Caldwell, was raised in South L.A. and attended Washington High in the Westmont neighborhood. He quickly developed an idiosyncratic but evocative palette of lyrics. Drakeo called it “nervous music” for good reason — his music drips with paranoia, but opens up to a rich inner world.

“I know how to code everything and I switch it up every time I get bored,” he told The Times in 2018. “People think I just make up words, but everything means something.”

After being discovered by local hip-hop production hero DJ Mustard, Drakeo helped define the region’s evolving rap sound, alongside peers like 03 Greedo, G Perico and Shoreline Mafia, in the wake of imaginative, challenging superstar acts of the 2010s like Tyler, the Creator and Kendrick Lamar.

On 2016’s “Impatient Freestyle,” he began with an evocative boast — “If I could write a movie I would re-create ‘The Exorcist’ / I’m heaven-sent, n— think twice who you messing with” — before quickly turning to the deprivations of jail: “Giving n— hell ‘cause up top they say the beds was full.”

Drakeo recorded several popular and acclaimed mixtapes, including 2018’s “Cold Devil” and 2020’s “Thank You For Using GTL.”

But his rap success arrived at a difficult time in his young life. Until last year, he was on trial in connection with the killing of a 24-year-old man in 2016. Drakeo had faced a potential life sentence on charges of first-degree murder, attempted murder and conspiracy to commit murder.

He recorded his vocals for “Thank You For Using GTL” via telephone while at Men’s Central Jail in L.A., the title a sly yet bleak allusion to the company that connects phone services in jail. The album, in which Drakeo’s voice comes through on a staticky phone line punctuated with the company’s automated messages, was hailed as one of the great pieces of art ever made behind bars.

His rap crew Stinc Team had been labeled a gang by L.A. County prosecutors, who played music videos of Drakeo holding weapons in court. On “GTL,” Drakeo took dark glee in how obsessed prosecutors were with using his rap career as evidence in his trial: “This might sound real, but it’s fictional / I love that my imagination gets to you,” he rapped on album closer “Fictional.”

After he was acquitted of felony murder and attempted murder charges, county prosecutors sought to retry Drakeo on conspiracy charges related to the slaying. Caldwell ultimately accepted a plea deal and was released in November 2020.

His lyrics alluded to an omnipresent sense of danger around him. “Don’t be shy, I got killers with me, stupid / I march with sticks, I ain’t worried ‘bout no groupies,” he rapped on “Talk To Me,” his biggest single to date, with over 32 million Spotify plays.

“I live a nervous life. I gotta look around and watch my back from police and these other [people] out here,” he told the Times in 2018. “[People] want to kill me. I can’t be driving around in $100,000 cars on the run, listening to soft-ass [music].”
Drakeo released his most recent studio album, “The Truth Hurts,” in February, with cameos from superstar Drake and Don Toliver. His most recent mixtape, “So Cold I Do Em 2,” came out on Dec. 7.

On Saturday, the L.A. Fire Department responded to a call at 8:40 p.m. about an altercation at the music festival being held at Banc of California Stadium in Exposition Park. A source who was not authorized to speak publicly identified the victim as Drakeo. The festival’s remaining sets, which were to feature the Isley Brothers, YG, Snoop Dogg and 50 Cent, were canceled.

In a statement Sunday morning, Snoop Dogg — a co-promoter of the festival with Live Nation — wrote on social media that he’s “saddened by the events that took place last night at the Once Upon a Time in L.A. festival...Last night I was in my dressing room when I was informed about the incident and chose to immediately leave the festival grounds. My prayers go out to everyone affected by the tragedy. Please take care, love one another and stay safe y’all. I’m praying for peace in hip-hop.”

Caldwell is survived by his son and brother, the L.A. rapper Ralfy the Plug.