The Questions Hip-Hop
Sean Kantrowitz connects with hip hop's biggest fans – rappers, DJs, producers, writers, comedians, actors, and everything in between – to test their rap trivia skills, discuss their careers, dissect albums, and talk about how the music changed their lives.
Recent Episodes
March 23, 2026
Secure the Bag: The Mailbag Episode
Patreon.com/thequestionshiphop Los Angeles: Pharrell Game Night April 1 It's the inaugural mailbag episode. Sean answers questions about music listening habits, creative innovation vs consistent sound, phone eti...
March 16, 2026
Making Illmatic - Mos Def 'The Ecstatic' w/ Ali Elabbady
Hear the uncut episode with full music and cues at Patreon.com/thequestionshiphop Los Angeles: Pharrell Game Night April 1 The Making Illmatic format is back! Sean Kantrowitz and MidaZ the BEAST welcome writer Ali Ela...
March 2, 2026
Minneapolis Nice vs ICE w/ Tufawon & Rob Van Vranken
A firsthand account from artist Tufawon and producer Rob Van Vranken about what is happening in Minneapolis and how communities are combatting the presence of ICE in their neighborhoods – and how you can help. Patreon.com/...
Feb. 16, 2026
Joe DeRosa (Questions Classic)
Originally broadcast on June 15, 2020. Comedian and hip-hop aficionado Joe DeRosa puts his hip-hop trivia skills to the test and talks about his favorite albums, artists, and songs in this throwback episode from the Instagram...
Feb. 9, 2026
J Dilla's Top Ten Underrated Tracks (Making Dill-Matic 2026)
Sean runs through his picks for the 10 most underrated songs in J Dilla's production catalog. (Note: this is an updated take on 2024's 'Making Dill-Matic' episode) Patreon.com/thequestionshiphop quest...
Feb. 2, 2026
2016 Draft w/ Lyric Jones and Optiks
You're posting photos of yourself from 2016, we're spending 2 hours drafting the highs and lows of hip-hop from 2016; we are not the same. Sean Kantrowitz and MidaZ the BEAST are joined by guests Lyric Jones and Optiks to com...
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