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.
Episodes
June 22, 2026 • 61 mins
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 jo...
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June 8, 2026 • 48 mins
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 ...
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June 1, 2026 • 121 mins
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)
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May 26, 2026 • 91 mins
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
questionshipho...
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March 30, 2026 • 98 mins
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: @sh...
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March 23, 2026 • 41 mins
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
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March 16, 2026 • 83 mins
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 t...
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March 2, 2026 • 70 mins
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 Fund...
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February 16, 2026 • 47 mins
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.
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The Questions Hip-Hop: Instagram
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February 9, 2026 • 58 mins
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
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youtube.com/thequestionshiphop
The Questions Hip-Hop: Instagram
Sean Kantrowitz: Instagram
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February 2, 2026 • 120 mins
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!
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January 19, 2026 • 112 mins
Sean and MidaZ the BEAST welcome back Sha Stimuli (No Bars Off Show) to the pod for a thorough analysis of Canibus' verse on Lost Boyz's 1997 "Beasts from the East." What makes a verse "good"? What impact can a verse have on a career, a culture, and the industry? Rap nerds only for this one.
Patreon.com/thequestionshiphop
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youtube.com/thequestionshiphop
yout...
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December 29, 2025 • 95 mins
*taps mic*
Is this thing on?
Taking a break from the hiatus to reflect back on some of the best moments from the podcast in 2025. Happy New Year, thanks for listening, and be sure to join the Patreon to get more episodes, content, mixes, and more!
Patreon.com/thequestionshiphop
questionshiphop.com
youtube.com/thequestionshiphop
http://beatjunkiesound.com/
The Qu...
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September 22, 2025 • 57 mins
Recorded live at the Beat Junkie Institute of Sound, Sean joins the Beat Junkies (DJ Babu, DJ Rhettmatic) for their RPM listening series, unpacking Visionaries 'Pangaea' album.
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youtube.com/thequestionshiphop
http://beatjunkiesound.com/
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September 8, 2025 • 51 mins
Recorded live at the Beat Junkie Institute of Sound, Sean joins the Beat Junkies (DJ Babu, DJ Rhettmatic) for their RPM listening series, deep diving into D-Styles' seminal 'Phantazmagorea' album.
Patreon.com/thequestionshiphop
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youtube.com/thequestionshiphop
http://beatjunkiesound.com/
The Questions Hip-Hop: Instagram
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Recorded live at the Beat Junkie Institute of Sound, Sean joins the Beat Junkies (DJ Babu, DJ Rhettmatic) for their RPM listening series, this time diving deep into Mobb Deep's classic 'The Infamous' with Rapper Big Noyd, Big Twinz, House Shoes, and Schott Free.
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http://beatjunkiesound.com/
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August 11, 2025 • 116 mins
Making Illmatic returns from a hiatus to The Questions Hip-Hop, as Sean Kantrowitz and MidaZ the BEAST are joined by emcee/artist Kap Kallous to explore Clipse's debut album 'Lord Willin' 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?
8:16 - 'Lord Willin' Background
20:55 - Album Ratings
28:33 - Intro
33:26 - Young Boy
40:23 - Virginia...
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August 4, 2025 • 60 mins
Recorded live at the Beat Junkie Institute of Sound, Sean joins the Beat Junkies (Mr. Choc, DJ Babu, DJ Rhettmatic) for their RPM listening series, with Blu and Exile sitting in for a conversation and breakdown of their debut album 'Below the Heavens.'
Patreon.com/thequestionshiphop
questionshiphop.com
youtube.com/thequestionshiphop
http://beatjunkiesound.com/
The Questions Hip-Hop: Instagram...
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July 28, 2025 • 58 mins
Sean Kantrowitz connects with journalist/author/hip-hop podcast OG Shawn Setaro to talk about the ins and outs of covering the Sean "Diddy" Combs trial for Complex.
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youtube.com/thequestionshiphop
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Sean Kantrowitz: Instagram
Shawn Setaro: Instagram
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July 21, 2025 • 98 mins
Originally broadcast on May 10 and May 17, 2021
Can't Knock the Shuffle features Sean Kantrowitz exploring the discography of an artist, and leaving it to an algorithm to choose which randomly-selected songs to ask the artist about. This classic episode features singer/songwriter and artist Esthero.
Songs:
"O.G. Bitch" (2003)
"Junglebook" feat Andre 3000...kind of ('Wikked Lil Girls,' 2005)
"Everything is Expensive" ('Eve...
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