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.
Q-Unique and Rhettmatic
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Q-Unique and Rhettmatic join the show to talk about their latest project 'The QR Code,' talk about the ways that their careers have evolved since the early days of the Arsonists and the Beat Junkies, and much more.
The Questions: @thequestionshiphop (IG)
Sean: @seandammit (IG)
Q-Unique
Rhettmatic
Email: [email protected]
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The Answers: GoodWaves Festival Recap
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New The Questions Hip-Hop T-Shirt Drop
My long-overdue recap of attending and participating in the GoodWaves Festival in Chicago this summer. Shout out to Murs and the whole team.
The Questions: @thequestionshiphop (IG)
Sean: @seandammit (IG)
Email: [email protected]
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Propaganda
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New The Questions Hip-Hop T-Shirt Drop
Propaganda shares the benefits and drawbacks to being labeled as "Christian hip-hop," the ways that his background as a schoolteacher shaped his podcast 'Hood Politics,' growing up in predominantly Mexican neighborhoods, AI, and much more.
The Questions: @thequestionshiphop (IG)
Sean: @seandammit (IG)
Propaganda: @prophiphop (IG)
Email: [email protected]
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Wildchild
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New The Questions Hip-Hop T-Shirt Drop
Wildchild joins the show to talk about his Oxnard origins, the early days of Lootpack, how he landed a solo song on Madvillain's 'Madvillainy,' his relationship with Madlib, his maturation as an artist and a father, and much more.
The Questions: @thequestionshiphop (IG)
Sean: @seandammit (IG)
Wildchild: @jdawildchild (IG)
Email: [email protected]
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Danny Hastings
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New The Questions Hip-Hop T-Shirt Drop
Renown photographer/filmmaker Danny Hastings joins the show to talk with Sean about the stories behind some of the most iconic album covers in hip-hop – including stories behind the making of the artwork for classics by Wu-Tang, KRS-ONE, Big Pun, Gang Starr, and many more.
The Questions: @thequestionshiphop (IG)
Sean: @seandammit (IG)
Danny Hastings: @dannyhastings (IG)
Email: [email protected]
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DJ Muggs
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New The Questions Hip-Hop T-Shirt Drop
Sean is joined by DJ Muggs – who reveals the stories behind randomly selected songs in his massive discography, including songs by Cypress Hill, GZA, Jay Worthy, his solo projects, and more.
The Questions: @thequestionshiphop (IG)
Sean: @seandammit (IG)
DJ Muggs: @djmuggs_the_black_goat (IG)
Email: [email protected]
questionshiphop.com
Open Mike Eagle & Kenny Segal
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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: [email protected]
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Talking Delicious Vinyl with 'Bust A Move' Author Peter Relic
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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: [email protected]
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DRAM
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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: [email protected]
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Ras Kass
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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" (Ra...Defari (Can't Knock the Shuffle CLASSIC)
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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)
Slug (of Atmosphere)
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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)
Mailbag 2: Electric Mail-A-Roo
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Sean answers questions (ha) in this mailbag episode.
The Questions: @thequestionshiphop (IG)
Sean: @seandammit (IG)
Making Illmatic: Noreaga 'N.O.R.E.' w/ Shinobi Stalin
Original Broadcast: January 16, 2023
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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: [email protected]
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Making Illmatic - Outkast 'ATLiens' w/ IMAKEMADBEATS
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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.
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Making Illmatic - Jaylib 'Champion Sound' w/ Supastition
Original broadcast: June 10, 2024
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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.'
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Slum Village (Can't Knock the Shuffle)
Original broadcast: May 20, 2024
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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)
"...
'Making Illmatic': Wu-Tang Clan 'Wu-Tang Forever' w/ IMAKEMADBEATS (Questions Classic)
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)
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https://www.weareunapologetic.com/
Making Illmatic: Sean Price 'Monkey Barz' w/ Top Shelf Premium
Originally Broadcast: June 19, 2023
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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: [email protected]
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Making Illmatic: Jay-Z 'The Blueprint 2' w/ Sha Stimuli
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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
Secure the Bag: The Mailbag Episode
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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.
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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 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?
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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.
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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:
...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 Live days of The Questions.
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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)
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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 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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Can-I-Pod: Examining Canibus' "Beasts from the East" Verse w/ Sha Stimuli
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.
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Greatest Hits - The Best of 2025
*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!
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RPM: Visionaries 'Pangaea' (Live at Beat Junkie Institute of Sound)
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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RPM: D-Styles 'Phantazmagorea' (Live at Beat Junkie Institute of Sound)
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.
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RPM: Mobb Deep 'The Infamous' feat. Big Twinz, Big Noyd, House Shoes, & More (Live at Beat Junkie Institute of Sound)
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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Making Illmatic - Clipse 'Lord Willin' w/ Kap Kallous
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 48:51 - Grindin' 59:18 - Hot Damn feat Ab-Liva and Rosco P. Coldchain 01:04:44 - Ma I Don't Love Her feat Faith Evans 01:11:31 - FamLay Freestyle 01:16:56...
RPM: Blu + Exile on 'Below the Heavens' (Live at Beat Junkie Institute of Sound)
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.'
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Shawn (Setaro) + Sean (Kantrowitz) on Sean ("Diddy" Combs)
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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Esthero (Can't Knock the Shuffle Classic)
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" ('Everything is Expensive', 2012)
"Streetlights" (Kanye West, '808s and Heartbreak', 2008)
"Amber and Tiger's Eye" ('We R in Need of...
Zilla Rocca (Questions Classic)
Originally broadcast on August 26, 2021.
Zilla Rocca (Call Out Culture podcast, Wrecking Crew) hops in the hot seat to talk all things hip-hop/music and puts his trivia skills to the ultimate test.
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Independent as F***: Ben Pedroche (Grown Up Rap)
Sean Kantrowitz speaks with London-based author Ben Pedroche, whose book 'Independent as F***: Underground Hip-Hop from 1995-2005' offers a comprehensive overview of the albums, artists, 12" records, and labels that shaped the genre in its arguably most-potent decade.
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2005 Draft w/ Justin Hunte and The Last MJ
The second Draft episode of The Questions Hip-Hop podcast takes an in-depth deep dive into the year 2005. Sean Kantrowitz, MidaZ the BEAST, Justin Hunte (The Company Man) and The Last MJ (Don't Quote Me podcast) comb through the year 2005, selecting their picks for Best Mainstream Album, Best Independent Album, Best Beat, Best Emcee, Best Verse, Best Guest Feature/Verse, Best Producer, Best Album Cover, and Best Video. Buckle up and get ready for some hot takes, debates, and a thoughtful look back at what was happening in hip-hop 20 (!) years ago.
Patreon.com/thequestionshiphop
...
El Da Sensei (Can't Knock the Shuffle Classic)
Originally broadcast on June 7, 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 El Da Sensei, the Newark rapper and members of Artifacts whose career spans several decades, groups, and solo projects.
Songs:
"Speakin'" ('Relax, Relate, Release', 2003)
"Live Noise" feat. Akrobatik (w/ The Returners, 'GT2: Nu World', 2010)
"Wrong Side of Da Tracks" (Artifacts, 'Between a Rock and a Hard Place', 1994)
"...
Gifted Gab (Questions Classic)
Originally broadcast on January 13, 2021.
Sean is joined by Seattle's self-proclaimed "Queen of Rap," Gifted Gab for a hilarious and insightful conversation about her career – as well as a game of hip-hop trivia.
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