Too $hort Talks Blow the Whistle, Working with Biggie & Tupac and New Album "Sir Too $hort, Vol. 2"

Too $hort Talks Blow the Whistle, Working with Biggie & Tupac and New Album "Sir Too $hort, Vol. 2"

From Zach Sang Show by Sangasong, LLC

September 4, 2026 · 1h 21m · Episode 1084

About this episode

Too $hort reflects on his extensive career in hip-hop, sharing stories about his music, collaborations, and personal experiences.

Too $hort joins us to look back on more than four decades in hip-hop and the stories behind one of the genre’s most enduring careers. He takes us back to Oakland in the ’80s, when he was selling $20 custom raps on cassette to local drug dealers, and explains how his voice and name became famous around the Bay Area before people even knew what he looked like. He also gets into the stories behind songs like “Freaky Tales” and “Blowjob Betty,” his mother’s reaction to his music, the meaning of being a “player,” and why his supposed retirement in 1996 was never quite what it seemed. Now 60 years old and still going strong, he breaks down his place in hip-hop history, from the ’90s East Coast–West Coast rivalry and the rise of hyphy to the Lil Jon collaboration that changed the course of his career and the making of “Blow the Whistle.” Too $hort shares what it was like recording with The Notorious B.I.G., Tupac and JAY-Z (the only rapper to do so!), including watching Biggie work without writing down his verses and the incredible speed of Tupac’s process. Plus, he talks working with Snow Tha Product, forming Mount Westmore with Snoop Dogg, Ice Cube and E-40, becoming a father later in…

People in this episode

Host: Zach Sang

Guest: Too $hort

Topics covered

Keywords

Mentioned in this episode

Books & works: Sir Too $hort, Vol. 2, Freaky Tales, Blowjob Betty, Blow the Whistle

Places: Oakland

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