Drakeo The Ruler

Drakeo the Ruler was a pillar of West Coast hip-hop and inspired a generation of rappers with his unique flow, vivid storytelling, and authentic personality, which bled into every song he recorded. Born Darrell Wayne Caldwell, throughout his life Drakeo not only fought against the systems that tried to block his path of success, but beat them with a sneer and the “nervous music” that would become a staple in Los Angeles rap. This new sound helped Drakeo catch the eye of DJ Mustard, who took fondly to the newcomer and helped power the remix to one of his early classics, “Mr. Get Dough.” From there, Drakeo the Ruler burst onto the Los Angeles rap scene hot with his 2015 debut mixtape, I Am Mr. Mosely. The tape changed the complexion of Southern Los Angeles, with Drakeo demanding respect by fearlessly injecting his slippery cadences into electric beats to create songs that bumped in the whip and on the streets. 

But after riding that momentum through two more mixtapes, Drakeo the Ruler was arrested in 2017 in what would mark the beginning of a long and targeted battle between the rapper, his Stinc Team crew, and the Los Angeles Police Department. Despite going to prison for several months after the LAPD raided a condo where he would often shoot music videos, Drakeo returned later in 2017 with one of his most successful mixtapes to date, Cold Devil, proving that no judicial bars formed against him could prosper. His bouts with the LAPD would continue until his last stint in prison, which ended when he was released on a plea deal in November 2020. Drakeo immediately released two more mixtapes in December, a testament to his warrior spirit and never-give-up ethos.

On Dec. 18, 2021, Drakeo the Ruler was stabbed in the neck and killed at the Once Upon a Time in LA festival, where he was set to perform. He was 28 years old. Drakeo the Ruler was the People’s Champion of Southern Los Angeles, the unsung hero who spat crooked flames and meant every word he nervously rhymed. He was a staple of the West Coast, and his legacy will extend far beyond the streets that raised him. As veteran journalist Jeff Weiss, who covered the late rapper from the beginning of his career, aptly put it, Drakeo will continue to Rule “once, always, and forever.”

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