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The Questions Hip-Hop

Published by The Questions Hip-Hop

  • Music
  • Music commentary
  • Music interviews

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. 

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On the charts

3 chart placements

Every published chart this podcast appears in, in the snapshot behind this page. Each one links to the chart it came off.

  1. Number 134Music interviewsAustralia
  2. Number 193Music interviewsCanada
  3. Number 148Music interviewsUnited States

From the feed

Recent episodes

The latest episodes published to this podcast’s own RSS feed. Titles and descriptions are the publisher’s.

  1. Open Mike Eagle & Kenny Segal

    Aug 26, 2026

    Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠ ⁠New The Questions Hip-Hop T-Shirt Drop⁠ Open Mike Eagle returns to the show and he's joined by producer Kenny Segal. The duo just released their first collaborative album 'DOOMED!' Sean and the duo talk relationships, gatekeeping, video games, technology, podcasting, and more. The Questions: ⁠⁠⁠⁠⁠@thequestionshiphop⁠⁠⁠⁠⁠ (IG) Sean: ⁠⁠⁠⁠⁠@seandammit⁠⁠⁠⁠⁠ (IG) Open Mike Eagle: open_mike_eagle (IG) Kenny Segal: kennysegal (IG) Email: sean@questionshiphop.com ⁠⁠⁠⁠⁠questionshiphop.com

  2. Talking Delicious Vinyl with 'Bust A Move' Author Peter Relic

    Aug 19, 2026

    Patreon.com/thequestionshiphop⁠⁠⁠⁠ New The Questions Hip-Hop T-Shirt Drop Sean connects with book author Peter Relic, whose 'Bust A Move: Matt Dike, Delicious Vinyl, and the Hip-Hop Hits That First Conquered Pop' offers a fascinating look at one of rap's most important Los Angeles record labels at a pivotal time in hip-hop history. The Questions: ⁠⁠⁠⁠@thequestionshiphop⁠⁠⁠⁠ (IG) Sean: ⁠⁠⁠⁠@seandammit⁠⁠⁠⁠ (IG) Peter Relic: ⁠⁠⁠ @reliconrecord (IG) Email: sean@questionshiphop.com ⁠⁠⁠⁠questionshiphop.com

  3. DRAM

    Aug 12, 2026

    Patreon.com/thequestionshiphop⁠⁠⁠ ⁠⁠⁠ORDER THE QUESTIONS HIP-HOP TRIVIA GAME⁠⁠⁠ DRAM joins the show to talk with Sean about the stories behind six randomly-selected songs from his catalog (picked by Sean's FYI.AI agent, Seanvo). They also discuss - in no particular order - favorite Outkast albums, cornbread, a personally-infuriating Mandela effect, Rick Rubin, and more. The Questions: ⁠⁠⁠@thequestionshiphop⁠⁠⁠ (IG) Sean: ⁠⁠⁠@seandammit⁠⁠⁠ (IG) DRAM: ⁠⁠⁠@shelley (IG) Email: sean@questionshiphop.com ⁠⁠⁠questionshiphop.com

  4. Ras Kass

    Aug 5, 2026

    Patreon.com/thequestionshiphop⁠⁠ ⁠⁠ORDER THE QUESTIONS HIP-HOP TRIVIA GAME⁠⁠ Ras Kass is celebrating some major milestones this year, from the 30th anniversary of his debut 'Soul on Ice' to the recent release of his latest album 'Leopard Eats Face.' Ras links up with Sean Kantrowitz at the FYI Campus to break down some of the stories behind his most conceptual songs, and how he uses his platform to talk about trauma, honesty, and the state of the world. Hear the stories behind: "The Evil That Men Do" (Soul on Ice, 1996) "Interview with a Vampire" (Rasassination, 1998) "Fun and Games" (Leopard Eats Face, 2026) "The Long Way" featuring Everlast (Soul on Ice 2, 2019) "Gods N The Hood" featuring Bishop Lamont, MK Assante, and Talib Kweli (Barmaggedon, 2013) "Bon Voyage" w/ Apollo Brown (Blasphemy, 2014) ...and much more! The Questions: ⁠⁠@thequestionshiphop⁠⁠ (IG) Sean: ⁠⁠@seandammit⁠⁠ (IG) Ras Kass: ⁠⁠@ras_kass (IG) Email: sean@questionshiphop.com ⁠⁠questionshiphop.com

  5. Defari (Can't Knock the Shuffle CLASSIC)

    Jul 29, 2026

    Patreon.com/thequestionshiphop⁠ ⁠ORDER THE QUESTIONS HIP-HOP TRIVIA GAME⁠ Original broadcast: March 3, 2023 Defari hops in the shuffle seat for this episode of Can't Knock the Shuffle. The Likwit Crew emcee shares the stories behind seven randomly selected songs from his decades-spanning catalog: "2 Places at the Same Time" (Likwit Junkies 2, 2020) "Steeple Chase" (Rare Poise, 2017) "People Trip" (Street Music, 2006) "SCANS" (The LJs, 2005) Dilated Peoples "Closed Session" (Neighborhood Watch, 2004) Montage One "Def B4 Dishonor" (MontageOne.COM 10.6.2 OGX, 2010) "Bionic" (1998) The Questions: ⁠@thequestionshiphop⁠ (IG) Sean: ⁠@seandammit⁠ (IG) Defari: ⁠@mr_defari⁠ (IG) Email: sean@questionshiphop.com ⁠questionshiphop.com

  6. Slug (of Atmosphere) (Questions Classic)

    Jul 22, 2026

    Join our PATREON ⁠⁠ORDER THE QUESTIONS HIP-HOP TRIVIA GAME⁠ Original Broadcast: June 13, 2022 Sean "Slug" Daley of independent hip-hop pioneers Atmosphere puts his hip-hop trivia skills to the test and shares stories from his career. We also talk about Del the Funky Homosapien, Black Star, Kendrick Lamar, Cypress Hill, crate-digging, touring, and much more. atmospheresucks.com The Questions: ⁠⁠@thequestionshiphop⁠⁠ (IG) Sean: ⁠⁠@seandammit⁠⁠ (IG)

  7. Mailbag 2: Electric Mail-A-Roo

    Jul 13, 2026

    ⁠ORDER THE QUESTIONS HIP-HOP TRIVIA GAME⁠ ⁠Patreon.com/thequestionshiphop⁠ Sean answers questions (ha) in this mailbag episode. The Questions: ⁠@thequestionshiphop⁠ (IG) Sean: ⁠@seandammit⁠ (IG)

  8. Making Illmatic: Noreaga 'N.O.R.E.' w/ Shinobi Stalin (Questions Classic)

    Jul 6, 2026

    Original Broadcast: January 16, 2023 ORDER THE QUESTIONS HIP-HOP TRIVIA GAME Patreon.com/thequestionshiphop Emcee/producer Shinobi Stalin joins Sean and MidaZ to examine Noreaga's 1998 debut 'N.O.R.E.' and find out if the album is improved or diminished by trimming to 10 songs. The Questions: @thequestionshiphop (IG) Sean: @seandammit (IG) MidaZ: @midazthebeast (IG) Shinobi Stalin: @shinobistalin (IG) Email: sean@questionshiphop.com questionshiphop.com

  9. Making Illmatic - Outkast 'ATLiens' w/ IMAKEMADBEATS

    Jun 29, 2026

    ⁠Patreon.com/thequestionshiphop⁠ ⁠questionshiphop.com⁠ ⁠ORDER THE QUESTIONS HIP-HOP TRIVIA GAME⁠ We're back with another 'Making Illmatic' episode – a thought experiment in which we attempt to condense an album down to 10 songs. Sean and MidaZ are joined once again by IMAKEMADBEATS to attempt to put Outkast's second album 'ATLiens' under the microscope. The Questions Hip-Hop: ⁠Instagram⁠ Sean Kantrowitz: ⁠Instagram⁠ MidaZ the BEAST: ⁠Instagram⁠ IMAKEMADBEATS: ⁠Instagram⁠

  10. Making Illmatic - Jaylib 'Champion Sound' w/ Supastition (Questions Classic)

    Jun 22, 2026

    Original broadcast: June 10, 2024 Patreon.com/thequestionshiphop questionshiphop.com ORDER THE QUESTIONS HIP-HOP TRIVIA GAME Sean and MidaZ the BEAST bring back the Making Illmatic format – a thought experiment in which they attempt to condense an album down to 10 songs – and this time the record going under the microscope is Jaylib's 'Champion Sound,' the collaborative project between J Dilla and Madlib. They're joined by returning MI guest Supastition, who also talks about his latest project, 'All That Was Left Unsaid.' The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram MidaZ the BEAST: Instagram Supastition: Instagram | Bandcamp

  11. Slum Village (Can't Knock the Shuffle) (Questions Classic)

    Jun 8, 2026

    Original broadcast: May 20, 2024 Patreon.com/thequestionshiphop questionshiphop.com ORDER THE QUESTIONS HIP-HOP TRIVIA GAME Slum Village (T3 and Young RJ) share the stories behind seven randomly selected songs from the SV catalog. The duo reflect on the group's evolution over the course of nearly three decades, from their early days with J Dilla to their most recent project, 2024's 'F.UN.' Songs explored in this episode: "To the Disco" ('F.U.N.', 2024) "Hear This" (feat Black Milk and Phat Kat) ('Slum Village,' 2005) "All Live" ('F.U.N.,' 2024) "Beej-N-Dem" ('Fantastic Vol. 1,' 1997) "We'll Show You" feat AB ('Villa Manifesto,' 2010) "Unisex" ('Trinity,' 2002) "Untitled/Fantastic" ('Fantastic Vol. 2', 2000) Slum Village https://www.instagram.com/officialslumvillage The Questions Hip-Hop: Instagram | Sean Kantrowitz: Instagram |

  12. 'Making Illmatic': Wu-Tang Clan 'Wu-Tang Forever' w/ IMAKEMADBEATS (Questions Classic)

    Jun 1, 2026

    Originally broadcast: May 30, 2022 Another installment of The Questions' 'Making Illmatic' series, in which Sean Kantrowitz and MidaZ the BEAST attempt to improve an album by trimming it down to 10 tracks. They're joined by founder of Memphis collective Unapologetic./producer IMAKEMADBEATS to take on the herculean task of trimming down Wu-Tang Clan's 1997 double-album 'Wu-Tang Forever.' The Questions: @thequestionshiphop (IG) Sean: @seandammit (IG) MidaZ: @midazthebeast (IG) IMAKEMADBEATS: @IMAKEMADBEATS (IG) questionshiphop.com https://www.weareunapologetic.com/

  13. Questions Classic- Making Illmatic: Sean Price 'Monkey Barz' w/ Top Shelf Premium

    May 26, 2026

    Originally Broadcast: June 19, 2023 Patreon.com/thequestionshiphop Sean and MidaZ are joined by Mark Rosado (Top Shelf Premium) in a Making Illmatic episode about Sen Price's debut solo album 'Monkey Barz.' What 10 songs will the three of them keep? The Questions: @thequestionshiphop (IG) Sean: @seandammit (IG) MidaZ: @midazthebeast (IG) Top Shelf Premium: @topshelfpremium (IG) Email: sean@questionshiphop.com questionshiphop.com

  14. Making Illmatic: Jay-Z 'The Blueprint 2' w/ Sha Stimuli

    Mar 30, 2026

    Patreon.com/thequestionshiphop Revisiting this classic episode from 2023: Sean and MidaZ return with another installment in the Making Illmatic series. This time they're joined by Sha Stimuli to take on the formidable task of trimming Jay-Z's double-album 'The Blueprint 2: The Gift and the Curse' down to just 10 songs. The Questions: @thequestionshiphop (IG) Sean: @seandammit (IG) MidaZ: @midazthebeast (IG) Sha Stimuli: @shastimuli (IG) questionshiphop.com

  15. Secure the Bag: The Mailbag Episode

    Mar 23, 2026

    ⁠⁠⁠⁠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 etiquette in 2026, and more. ⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠Instagram⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠Instagram⁠⁠⁠⁠

  16. Making Illmatic - Mos Def 'The Ecstatic' w/ Ali Elabbady

    Mar 16, 2026

    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 Elabbady (aka Egypto Knuckles) to do a deep dive into Mos Def's The Ecstatic and attempt to trim the album down to its 10 best songs. How do you trim this LP down to 10 songs and does doing so help or hurt the album? ⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠ ⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠Instagram⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠Instagram⁠⁠⁠ MidaZ the BEAST: ⁠⁠⁠Instagram⁠⁠⁠ Ali Elabbady: Instagram

  17. Minneapolis Nice vs ICE w/ Tufawon & Rob Van Vranken

    Mar 2, 2026

    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/thequestionshiphop⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠⁠ Direct Funding for Constitutional Observer training: https://linkin.bio/unidosmn/ Direct Funding for Immigrant Advocacy Organizers: https://linkin.bio/mncopal/ Rent Relief Funds: https://www.standwithminnesota.com/ Direct Food Distribution: https://www.dhhmn.com/operations Direct Family Funding: https://linktr.ee/smittenkittenmn Direct Funding for Organizers: https://linktr.ee/powwowgrounds Direct support for immigrant activists: https://www.instagram.com/miracmn Press: https://www.instagram.com/onsitepublicmedia https://www.instagram.com/bygeorgiafort https://www.instagram.com/blck.press https://www.instagram.com/sahanjournal https://www.instagram.com/mercadomedia1 https://www.instagram.com/unicorn.riot The Questions Hip-Hop: ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ Tufawon: ⁠Instagram⁠ Rob Van Vranken: Instagram

  18. Joe DeRosa (Questions Classic)

    Feb 16, 2026

    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 Live days of The Questions. ⁠⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠ Joe DeRosa: Instagram

  19. J Dilla's Top Ten Underrated Tracks (Making Dill-Matic 2026)

    Feb 9, 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠

  20. 2016 Draft w/ Lyric Jones and Optiks

    Feb 2, 2026

    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 comb through the benchmarks of a year that may not instantly ring a bell for you when it comes to hip-hop history – but trust, there's plenty to dig into here! Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ MidaZ the BEAST: ⁠Instagram⁠ Lyric Jones: Instagram Optiks: Instagram

Ranking source

Apple Podcasts rankings via the Mato Topic Intelligence Platform.

Observed September 20, 2026.

Apple and Apple Podcasts are trademarks of Apple Inc., registered in the U.S. and other countries.

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