Gangsta Rap Episodes

A real tycoon is in the building. Questlove sits down with Vallejo’s own E-40, the Yay Area legend who was selling records out of his trunk back when getting a major-label deal felt impossible. He built his own label, financed his projects independently, and gave Hip-Hop an entire dictionary of slang and similes. Now, with Turning My Money Over—a historic 40-song quadruple album—Earl Stevens isn’t slowing down. E-40 talks about growing up on Magazine Street in Vallejo’s Hillside neighborhood, the New York and Bay Area rappers who shaped his voice, and the year at Grambling State that taught him how to make it on his own. He explains how The Click navigated distribution through consignment sheets, mom-and-pop stores, and even rim shops—and how VHS duplication helped change the game for independent artists. 40 Water recalls his dealings with Tupac, advocates for members of the Hieroglyphics crew, and shares how being doubted by a room full of DJs decades ago only pushed him to go har…

Vince Staples sits down with Questlove for a rare, unflinching conversation about community, survival, and growing as an artist without losing yourself. Speaking about his latest album, Crybaby, Vince shares hard-earned truths and wisdom from his life, cutting through myth and memory with his trademark clarity and dark humor. The two artists explore happiness, death, faith, hobbies, and the music industry’s shifting gaze on Black artists—while tracing Vince’s journey from riding the bus to Hollywood studios to becoming one of music's sharpest minds.

In the first of a two-part Questlove Supreme interview, Ice-T looks back at his Hip Hop origins. He and Questlove discuss their recent 50th anniversary Grammy Hip Hop celebration performance. Ice also tells Team Supreme about his earliest records, his time in the Army, and how he became one of the first rappers with a lavish lifestyle.