Drakeo the Ruler

Caldwell was raised in South Los Angeles by a single mother. He attended Washington High School in nearby Westmont.[3] Also, his blood brother is other local Los Angeles rapper, Ralfy the Plug.

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,[3] 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.[6]

He released his second project, I Am Mr. Mosely 2, on 21 July 2016, with features including Mozzy, Skeme, and Philthy Rich.[7] He followed this up with the release of So Cold I Do Em in December, which included one 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.[4][8] 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".[9] Similarly, Grant Rindner of Complex called it "one of the most impressive California rap projects in years".[10] 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.[11]

He released the project, Thank You for Using GTL, in June 2020, while incarcerated.[12] His ninth mixtape, The Truth Hurts, was released on February 24, 2021. The mixtape contains notable guest appearances from Don Toliver, and Drake on the song "Talk to Me".[13]

In January 2017, Caldwell was arrested by the LAPD when they raided a condo where he regularly shot music videos. He was subsequently held at Men's Central Jail after being charged with unlawful possession of a firearm by a felon.[14] He was released in November.[4]

In March 2018, he was arrested again, this time charged with first-degree murder, attempted murder and conspiracy to commit murder. The charges stemmed from a December 2016 shooting in Carson, California where one person was killed and two were injured.[15] He was facing life in prison.[16] Simultaneously, members of his Stinc Team collective, including his brother Ralfy the Plug, were arrested in San Francisco on a variety of charges.[17]

On July 25, 2019, he was acquitted of his murder and attempted murder charges in a Compton courthouse.[18] However, the district attorney decided to refile charges of criminal gang conspiracy and shooting from a motor vehicle in August, two counts that resulted in a hung jury during his initial trial.[19] His trial date was set for August 3, 2020. While incarcerated, he recorded Thank You for Using GTL, which Pitchfork called "likely the greatest rap album ever recorded from jail".[12] He was released from jail in November 2020 after the district attorney's office offered him a plea deal following three years in jail.[20]