Drakeo The Ruler has been played over 10 times on NTS, first on 11 December 2017. Drakeo The Ruler's music has been featured on 14 episodes.

Darrell Caldwell (December 1, 1993 - December 19, 2021 in Los Angeles, California), known professionally as Drakeo the Ruler, was an American rapper and songwriter based in Los Angeles, California. He was known for his unique flow as well as his "oddly expressive, poetic word-choices", leading the Los Angeles Times to call him "the most original West Coast stylist in decades."

After recording a handful of mixtapes with much more of a trap influence than the West Coast hip hop he became known for, he was discovered by DJ Mustard, who remixed his song Mr. Get Dough. The song, which premiered on WorldStar in April 2015, became his breakout song, and has amassed over 6.2 million YouTube views (as of August 2019). Six months later, in October, Drakeo release his official debut mixtape, I Am Mr. Mosely, as his first project under Mustard's 10 Summers label.

He released his second project, I Am Mr. Mosely 2, on 21 July 2016, with features which included Mozzy, Skeme, and Philthy Rich. He followed this up with the release of So Cold I Do Em in December, which included of his most popular songs, Impatient Freestyle.

After his jail release in November 2017, he recorded a 16-track mixtape, Cold Devil, in 10 days, and released it the following month. Paul A. Thompson of Pitchfork described it as "the most compelling album of the Los Angeles emcee’s career," adding that his "avant deadpan and impressionistic relationship to the beat" is "icy and unforgettable."Similarly, Grant Rindner of Complex called it "one of the most impressive California rap projects in years". He released music videos for Flu Flamming, Big Banc Uchies and Out the Slums within a month, amassing 4.4 million, 3.6 million and 4.0 million YouTube views, respectively. Flu Flamming was also notably remixed by Lil Yachty, and Big Banc Uchies by Shy Glizzy. The music video for Roll Bounce was released in September, with Drakeo in jail awaiting trial.

Caldwell was stabbed backstage at around 8:30 p.m. on December 18, 2021, during the Once Upon a Time in LA festival. Initial eyewitness accounts reported that he was stabbed in the neck during an altercation; later, his mother Darrylene Corniel revealed in an interview with Rolling Stone that Caldwell, his brother, and their entourage were attacked by "around 40, 60 men" in masks around the time of YG's arrival to the venue, and that Caldwell had been stabbed in the neck. Paramedics arrived at the scene at around 8:40 p.m. and transported Caldwell to a nearby hospital in critical condition. The event itself was cancelled shortly afterward.

Caldwell was pronounced dead as a result of his stab wounds at around midnight on December 19, 2021, roughly four hours after the initial altercation. As of December 21, 2021, the Los Angeles Police Department is investigating his death as a homicide.