Born Darrell Caldwell, Drakeo was raised in the Hundreds section of South Central by his preschool teacher mother. Drawn to rapping as a means to avoid the pitfalls of street life, he began shaping his signature style with some help from his brother, who raps under the moniker Ralfy the Plug. In 2015, Drakeo caught the attention of DJ Mustard, who remixed the then-fledgling MC's "Mr. Get Dough"; YouTube views of its official video quickly exceeded four million. Mustard also hosted the parent release, I Am Mr. Mosely, which proved to be Drakeo's breakout tape.
Over the next couple years, Drakeo issued a sequel to I Am Mr. Mosely, along with So Cold I Do Em and Cold Devil. The latter two featured "Impatient Freestyle" and "Flu Flamming," two of the most popular tracks from his early catalog. While incarcerated in 2020 -- he'd previously beat a murder charge, but was held due to a subsequent charge of gang conspiracy and shooting from a motor vehicle -- he issued #FreeDrakeo, which collected stray material, and Thank You for Using GTL, titled in reference to the telecommunications company that enabled him to record over the phone. That November, Drakeo was released from jail, freed after a plea agreement. (He maintained that Los Angeles' outgoing district attorney held a vendetta against him.) Wasting no time, he issued We Knew the Truth, Because Y'All Asked, and The Truth Hurts during the tail-end of 2020 and early 2021. The last of those tapes included guest verses from Drake and Don Toliver.
On December 18, 2021, Drakeo was stabbed backstage at the Once Upon a Time in L.A. Festival, passing away hours later on December 19, 2021. He was 28 years old. ~ Andy Kellman & James Christopher Monger, Rovi