Drakeo The Ruler has been played over 30 times on NTS, first on 11 December 2017. Drakeo The Ruler's music has been featured on 32 episodes.

Darrell Caldwell (December 1, 1993 – December 19, 2021), professionally known as Drakeo the Ruler, was a groundbreaking rapper and songwriter from Los Angeles, California. Widely regarded as the greatest rapper of his generation, he earned acclaim for his uniquely expressive flow, poetic word choices, and distinctive West Coast sound. His style revolutionized the Los Angeles rap scene, leading the Los Angeles Times to call him "the most original West Coast stylist in decades." Throughout his career, he consistently garnered praise for his innovative approach to music, solidifying his legacy as a trailblazer in the genre.

Drakeo first gained recognition with a series of mixtapes that showcased a trap-influenced sound before fully embracing the West Coast hip hop style he would later define. His breakthrough came with the 2015 remix of "Mr. Get Dough" by DJ Mustard, which quickly amassed millions of views on WorldStar, propelling him into the limelight. His debut mixtape, I Am Mr. Mosely (2015), released under Mustard’s 10 Summers label, set the stage for his rise, showcasing his unmatched lyrical dexterity and deadpan delivery.

In 2016, Drakeo released his follow-up project, I Am Mr. Mosely 2, which featured collaborations with notable artists like Mozzy, Skeme, and Philthy Rich. He continued to build momentum with the release of So Cold I Do Em later that year, which included the hit "Impatient Freestyle." His sound began to solidify with the release of Cold Devil in 2017, recorded in just 10 days following his jail release. Cold Devil received widespread critical acclaim, with Pitchfork describing it as "the most compelling album of his career" and Complex calling it "one of the most impressive California rap projects in years."

Drakeo's influence extended beyond his music, as he became a key figure in shaping modern West Coast hip hop. His collaborations with artists such as Lil Yachty, Shy Glizzy, and others showcased his versatility, with hits like "Flu Flamming," "Big Banc Uchies," and "Out the Slums" dominating the charts. His music videos consistently garnered millions of views, cementing his position as a leader in the rap game.

Tragically, Drakeo's life was cut short at the age of 28. On December 18, 2021, during the Once Upon a Time in LA festival, he was fatally stabbed in an altercation backstage. Despite being rushed to the hospital, he succumbed to his injuries on December 19, 2021. His death, which occurred shortly after the altercation, sent shockwaves through the music world, and his loss was felt deeply by fans and fellow artists alike. As of December 21, 2021, the Los Angeles Police Department was investigating his death as a homicide.

In his short but influential tenure, Drakeo the Ruler’s impact on Los Angeles rap and the broader hip hop landscape is undeniable. His music continues to resonate with fans, and his legacy as the greatest rapper of Los Angeles remains firmly intact.