History of Drakeo the Ruler in Timeline

By Popular Timelines Editorial Team · Updated: March 12, 2025

Darrell Wayne Caldwell (Drakeo the Ruler) was a Los Angeles rapper known for his unique flow and poetic lyricism. Gaining recognition for his distinctive style, he was hailed as an original voice in West Coast hip-hop. His single "Talk to Me" charted in 2021, preceding his debut studio album, The Truth Hurts.

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Full Timeline

December 1, 1993: Drakeo the Ruler's Birth

On December 1, 1993, Darrell Wayne Caldwell, known professionally as Drakeo the Ruler, was born. He would later become a prominent rapper from Los Angeles, known for his unique rapping flow and lyricism.

Others born on this day/year

April 14, 2015: Release of Mr. Get Dough Remix

On April 14, 2015, DJ Mustard remixed Drakeo the Ruler's song "Mr. Get Dough", which premiered on WorldStarHipHop, becoming his breakout song.

July 21, 2016: Release of I Am Mr. Mosely 2

On July 21, 2016, Drakeo the Ruler released his second project, I Am Mr. Mosely 2, featuring Mozzy, Skeme, and Philthy Rich.

December 2016: Shooting Incident in Carson

In December 2016, a shooting occurred in Carson, California, resulting in one death and two injuries, which later led to Drakeo the Ruler's arrest.

January 2017: Arrest for Firearm Possession

In January 2017, Drakeo the Ruler was arrested by the LAPD and charged with unlawful possession of a firearm by a felon.

November 2017: Jail Release

In November 2017, Drakeo the Ruler was released from jail.

March 2018: Arrest for Murder and Conspiracy

In March 2018, Drakeo the Ruler was arrested and charged with first-degree murder, attempted murder, and conspiracy to commit murder, stemming from the December 2016 shooting.

July 25, 2019: Acquittal of Murder Charges

On July 25, 2019, Drakeo the Ruler was acquitted of his murder and attempted murder charges in a Compton courthouse.

August 2019: "Mr. Get Dough" Views

As of August 2019, Drakeo the Ruler's breakout song, "Mr. Get Dough", amassed over 6.2 million views on YouTube.

June 2020: Release of Thank You for Using GTL

In June 2020, Drakeo the Ruler released the project Thank You for Using GTL, which was recorded from phone calls from jail.

August 3, 2020: Trial Date Set

On August 3, 2020, Drakeo the Ruler's trial date was set for criminal gang conspiracy and shooting from a motor vehicle.

November 2020: Release from Jail

In November 2020, Drakeo the Ruler was released from jail after accepting a deal from the District Attorney's office, pleading guilty to shooting from a vehicle.

February 24, 2021: Release of The Truth Hurts

On February 24, 2021, Drakeo the Ruler's official album debut, The Truth Hurts, was released, featuring Don Toliver and Drake.

December 18, 2021: Stabbing at Once Upon a Time in LA Festival

On December 18, 2021, Drakeo the Ruler was stabbed backstage during the Once Upon a Time in LA festival and was transported to a nearby hospital in critical condition.

December 19, 2021: Drakeo the Ruler's Death

On December 19, 2021, Drakeo the Ruler passed away, marking the end of his life and career as a rapper. His unique style had a significant impact on the West Coast hip-hop scene.

December 21, 2021: Investigation of Drakeo's Death

On December 21, 2021, the Los Angeles Police Department continued to investigate Drakeo the Ruler's death as a homicide, and he was interred at Forest Lawn Memorial Park.

January 2023: Lawsuit Against Live Nation

In January 2023, a Los Angeles County Superior Court judge allowed a lawsuit against Live Nation, filed by Drakeo the Ruler's mother, to proceed, citing negligence and lax security.