The Questions Hip-Hop podcast artwork

PODCAST · music

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. 

  1. 173

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

    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

  2. 172

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

  3. 171

    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? ⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠ ⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠Instagram⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠Instagram⁠⁠⁠ MidaZ the BEAST: ⁠⁠⁠Instagram⁠⁠⁠ Ali Elabbady: Instagram

  4. 170

    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/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

  5. 169

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

  6. 168

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

  7. 167

    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! 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

  8. 166

    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. Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠⁠ youtube.com/@nobarsoffshow The Questions Hip-Hop: ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠ MidaZ the BEAST: Instagram Sha Stimuli: Instagram No Bars Off: Instagram

  9. 165

    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! ⁠⁠⁠⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠http://beatjunkiesound.com/⁠⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠

  10. 164

    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. ⁠⁠⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠http://beatjunkiesound.com/⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠ Beat Junkie Institute of Sound: ⁠⁠⁠Instagram⁠

  11. 163

    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. ⁠⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠⁠ ⁠⁠http://beatjunkiesound.com/⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ Beat Junkie Institute of Sound: ⁠⁠Instagram⁠

  12. 162

    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. ⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠ ⁠http://beatjunkiesound.com/⁠ The Questions Hip-Hop: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ Beat Junkie Institute of Sound: ⁠Instagram⁠

  13. 161

    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 - When the Last Time 01:21:29 - Ego 01:27:18 - Comedy Central feat Fabolous 01:30:56 - Let's Talk About It feat. Jermaine Dupri 01:37:43 - Gangsta Lean 01:43:52 - I'm Not You feat. Jadakiss, Styles P, & Rosco P. Coldchain 01:49:07 - Grindin' Remix feat. Birdman, Lil Wayne, & N.O.R.E./Grindin' (Selector Remix) feat Sean Paul, Bless, & Kardinal Offishall 01:52:31 - Final Ten/Outro ⁠Patreon.com/thequestionshiphop⁠⁠⁠ ⁠⁠⁠questionshiphop.com⁠⁠⁠ ⁠⁠⁠youtube.com/thequestionshiphop⁠⁠ The Questions Hip-Hop: ⁠⁠Instagram⁠⁠ Sean Kantrowitz: ⁠⁠Instagram⁠⁠ MidaZ the BEAST: ⁠⁠Instagram⁠⁠ Kap Kallous: Instagram

  14. 160

    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.' ⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠ http://beatjunkiesound.com/ The Questions Hip-Hop: ⁠⁠⁠⁠Instagram⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠Instagram⁠⁠⁠ Beat Junkie Institute of Sound: Instagram Blu: Instagram Exile: Instagram

  15. 159

    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. Patreon.com/thequestionshiphop⁠⁠⁠⁠ ⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠ ⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠Instagram⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠Instagram⁠⁠ Shawn Setaro: Instagram

  16. 158

    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 a Musical Revolution!', 2004) "Breath From Another" ('Breath From Another,' 1998) "Gimme Some Time" (2019) ⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠⁠ esthero.net The Questions Hip-Hop: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠ Esthero: Instagram

  17. 157

    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. ⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠ ⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠ ⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠Instagram⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠Instagram⁠⁠ Zilla Rocca: Instagram

  18. 156

    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. Patreon.com/thequestionshiphop⁠⁠⁠ ⁠⁠⁠questionshiphop.com⁠⁠⁠ ⁠⁠⁠youtube.com/thequestionshiphop⁠⁠ The Questions Hip-Hop: ⁠⁠Instagram⁠⁠ Sean Kantrowitz: ⁠⁠Instagram⁠ Ben (Grown Up Rap): Instagram

  19. 155

    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 ⁠⁠questionshiphop.com⁠⁠ ⁠⁠youtube.com/thequestionshiphop⁠ The Questions Hip-Hop: ⁠Instagram⁠ Sean Kantrowitz: ⁠Instagram⁠ MidaZ the BEAST: ⁠Instagram⁠ Justin Hunte: Instagram The Last MJ: Instagram

  20. 154

    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) "It Takes Two" (w/ Sadat X, 'XL,' 2018) "Money" feat Roc Marciano and Reef the Lost Cause ('The Money EP', 2009) "Got Fire" (w/ The Returners, 'Global Takeover', 2008) "31 Bumrush" (Artifacts, 'That's Them,' 1997) ⁠⁠Patreon.com/thequestionshiphop⁠⁠⁠⁠ ⁠⁠⁠⁠questionshiphop.com⁠⁠⁠⁠ ⁠⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠⁠Instagram⁠⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠⁠Instagram⁠⁠ El Da Sensei: ⁠Instagram

  21. 153

    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. ⁠Patreon.com/thequestionshiphop⁠⁠⁠ ⁠⁠⁠questionshiphop.com⁠⁠⁠ ⁠⁠⁠youtube.com/thequestionshiphop⁠⁠⁠ The Questions Hip-Hop: ⁠⁠⁠Instagram⁠⁠⁠ Sean Kantrowitz: ⁠⁠⁠Instagram⁠ Gifted Gab: Instagram

  22. 152

    Making Illmatic - Nas 'It Was Written' w/ Jamil Honesty

    Making Illmatic returns to The Questions Hip-Hop, as Sean Kantrowitz and MidaZ the BEAST are joined by emcee/producer Jamil Honesty to deep dive into Nas's 'It Was Written' and attempt to scale 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? Patreon.com/thequestionshiphop⁠⁠ ⁠⁠questionshiphop.com⁠⁠ ⁠⁠youtube.com/thequestionshiphop⁠ The Questions Hip-Hop: ⁠Instagram⁠ Sean Kantrowitz: ⁠Instagram⁠ MidaZ the BEAST: ⁠Instagram⁠ Jamil Honesty: ⁠Instagram

  23. 151

    DJ Skizz (Questions Classic)

    Originally broadcast on Feb 3, 2021. Sean is joined by producer/DJ Skizz to talk about his career in hip-hop and producing for the likes of Roc Marciano, Freeway, Sean Price, and many others. And of course – to put his hip-hop trivia skills to the test. Patreon.com/thequestionshiphop⁠⁠ ⁠⁠questionshiphop.com⁠⁠ ⁠⁠youtube.com/thequestionshiphop⁠⁠ The Questions Hip-Hop: ⁠⁠Instagram⁠⁠ Sean Kantrowitz: ⁠⁠Instagram⁠

  24. 150

    Episode 200 Celebration!

    200th Episode Celebration! Sean recounts the 12 Most Important Moments in the podcast's history. ⁠Patreon.com/thequestionshiphop⁠⁠⁠ ⁠⁠⁠questionshiphop.com⁠⁠⁠ ⁠⁠⁠youtube.com/thequestionshiphop⁠⁠ The Questions Hip-Hop: ⁠⁠Instagram⁠⁠ Sean Kantrowitz: ⁠⁠Instagram⁠

  25. 149

    Lord Digga (Questions Classic)

    Patreon.com/thequestionshiphop⁠ ⁠questionshiphop.com⁠ ⁠youtube.com/thequestionshiphop⁠ Originally broadcast on March 16, 2021. Rapper/producer Lord Digga has collaborated with some absolute legends throughout his career, including Notorious B.I.G. (with three songs on his classic debut 'Ready to Die'), Ol' Dirty Bastard, Masta Ace, and many more. Digga shares stories from his career, tests his hip hop trivia skills, and answers fan questions in this classic episode of The Questions. The Questions Hip-Hop: ⁠Instagram⁠ Sean Kantrowitz: ⁠Instagram⁠

  26. 148

    Mathematics (Can't Knock the Shuffle)

    Patreon.com/thequestionshiphop questionshiphop.com Sean connects with Wu-Tang Clan's Mathematics for a "Can't Knock the Shuffle"-themed episode, powered by the AI in FYI.AI and covering the stories behind six randomly-selected Wu songs produced by Mathematics. They also talk about the latest Mathematics-produced Wu-Tang album 'Black Samson: The Bastard Swordsman.' Mathematics "Respect Mine" feat. Raekwon, Method Man, & Cappadonna (Love, Hell or Right, 2003) Wu-Tang Clan & Mathematics "Mandingo" (Black Samson, The Bastard Swordsman, 2025) Ghostface Killah "Mighty Healthy" (Supreme Clientele, 2000) Wu-Tang Clan "Do You Really (Thang Thang)" (The W, 2000) Method Man and Redman "Fire Ina Hole" (Blackout!, 1999) Wu-Tang Clan "Lesson Learn'd" (The Saga Continues, 2017) The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Mathematics: Instagram

  27. 147

    7L (Czarface, 7L & Esoteric) (Questions Classic)

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Originally broadcast on November 18, 2020. Digging in the Questions Classic crates for this throwback episode featuring DJ and producer 7l of Czarface and 7L & Esoteric. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram 7L : Instagram

  28. 146

    Making Illmatic - Cannibal Ox 'The Cold Vein' w/ Dart Adams

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Esteemed hip-hop historian and journalist Dart Adams returns to the Making Illmatic series of The Questions Hip-Hop, joining Sean Kantrowitz and MidaZ the BEAST in examining Cannibal Ox's debut album 'The Cold Vein.' How do you trim this LP down to 10 songs and does doing so help or hurt the album? The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram MidaZ the BEAST: Instagram Dart Adams: Instagram

  29. 145

    Slimkid3 (Can't Knock the Shuffle Classic)

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Originally broadcast on May 24, 2021. Simply put, Tre Hardson aka Slimkid3 is a legend. Hip hop was forever changed in 1992 when his group the Pharcyde emerged onto the scene with their classic debut album 'Bizarre Ride II The Pharcyde.' The group brought a decidedly animated and imaginative element to their songwriting and presence on the microphone – and Tre definitely stood out with his distinct melodic voice; you could really even say that a lot of these rappers who sing owe a bit to Slimkid3. The Pharcyde’s second album Labcabincalifornia sported a darker sound (and early contributions from the great Jay Dee aka Jay Dilla) that reflected the frustration the group was going through with both the industry – and internally. Tre did one last album with the group (2000’s Plain Rap) before embarking on a solo career that also has seen him team up with DJ Nu-Mark from Jurassic 5, Ozomatli, and occasional reunions with various members of his Pharcyde brethren – and today they are back at it (as a trio), touring the world and possibly poised to release new music soon. In this Can't Knock the Shuffle classic, we break down stories behind the following songs: "Groupie Therapy" (Pharcyde 'Labcabincalifornia', 1995) "Trust" (Pharcyde 'Plain Rap', 2000) "King" feat Diamond D and K-Natural ('Slimkid3 & Nu-Mark', 2016) "Life is Love" ('Liberation', 2002) "Pick It Up" feat Dillon Cooper (TRDMRK, 2019) "4 Better or 4 Worse" (Pharcyde 'Bizarre Ride II the Pharcyde', 1992) The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Slimkid3: Instagram

  30. 144

    Russell Peters (Questions Classic)

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Originally broadcast on May 25, 2020. Digging in the Questions Classic crates for this throwback episode featuring comedian, DJ, and hip-hop champion Russell Peters. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Russell Peters: Instagram

  31. 143

    Thank You, Roy Ayers w/ DJ Steve1der

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Sean Kantrowitz and DJ Steve1der pay tribute to Roy Ayers, highlighting not just his contributions to music but specifically the ways in which his compositions informed the DNA of so many hip-hop songs through sampling, interpolation, and collaborations. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Steve1der: Instagram

  32. 142

    Apathy (Questions Classic)

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Originally broadcast on February 17, 2021. We revisit the IG Live broadcast featuring Apathy (Demigodz, Army of the Pharoahs). Ap talks about his artistry, his fandom of his favorite emcees, and puts his hip-hop trivia skills to the test. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Apathy: Instagram

  33. 141

    1995 Draft w/ Trackstar the DJ and Philaflava

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop It's the inaugural Draft episode of The Questions Hip-Hop podcast. Sean Kantrowitz, MidaZ the BEAST, Trackstar the DJ (Run the Jewels, Killer Mike), and Jason Gloss (Philaflava) are combing through the year 1995, selecting their picks for Best Album, Best Beat, Best Emcee, Best Verse, Best Guest Feature/Verse, Best Producer, and Best Album Cover. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram MidaZ the BEAST: Instagram Trackstar the DJ: Instagram Philaflava: Instagram

  34. 140

    Making Illmatic - Redman 'Muddy Waters Too' w/ Zilla Rocca

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Uncharted Making Illmatic territory as Sean Kantrowitz and MidaZ the BEAST give the Making Illmatic treatment to Redman's 2024 album 'Muddy Waters Too,' the most recent - and longest! - LP to get the MI treatment yet. They're joined by returning guest Zilla Rocca (Call-Out Culture, Wrecking Crew) to attempt to shave the 32-song album down to its 10 best songs – and to decide if doing so helps or hurts the record. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram MidaZ the BEAST: Instagram Zilla Rocca: Instagram

  35. 139

    Bahamadia (Can't Knock the Shuffle Classic)

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Originally broadcast on November 11, 2020. Revisiting Bahamadia's appearance on Can't Knock the Shuffle, in which she and Sean explore the stories behind these randomly-selected songs from her catalog: "Innovation" ('Kollage', 1996) "Transcend" (King Britt, 'Adventures in Lo-Fi', 2003) "Proceed III" (The Roots, 1994) "Dialed Up 2" ('Dialed Up 2', 2017) "Thank You" ('Good Rap Music', 2006) "One-4-Teen (Funky For You)" ('BB Queen', 2000) "Here" (2015)

  36. 138

    Leslie "Big Lez" Segar (Questions Classic)

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop Originally broadcast on December 9, 2020. Steve1der connects with hip-hop TV host, radio personality, dancer, and choreographer Leslie "Big Lez" Segar to talk to her about the many facets of her career and to put her hip-hop trivia skills to the test! The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Steve1der: Instagram Leslie Segar: Instagram

  37. 137

    Making Illmatic - Roc Marciano 'Marcberg' w/ Dart Adams

    Patreon.com/thequestionshiphop questionshiphop.com youtube.com/thequestionshiphop The first 'Making Illmatic' episode of 2025 finds Sean Kantrowitz and MidaZ the BEAST joined by hip-hop pundit/writer Dart Adams to take a deep dive into Roc Marciano's classic debut album 'Marcberg.' The trio must trim the album down to its 10 best tracks – but which ones will make the cut? And does doing this help or hurt 'Marcberg'? The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram MidaZ the BEAST: Instagram Dart Adams: Instagram

  38. 136

    Marcus J. Moore

    Patreon.com/thequestionshiphop questionshiphop.com Buy the Questions Hip-Hop Trivia Game Sean is joined by author and music journalist Marcus J. Moore to discuss the current state of music journalism, the process of writing his latest book 'High and Rising: A Book About De La Soul,' and the controversy that followed its publication late last year. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Marcus J. Moore: Instagram

  39. 135

    Brother Ali & Dee-1

    Patreon.com/thequestionshiphop questionshiphop.com Buy the Questions Hip-Hop Trivia Game Brother Ali and Dee-1 join Sean for an in-person interview as the duo travel the United States on the Satisfied Soul Tour. Deep conversation and some real perspective from two artists who have never been afraid to speak truth through their music. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Brother Ali: https://brotherali.com | Instagram Dee-1: https://www.dee1music.com | Instagram

  40. 134

    DJ Doo Wop (Questions Classic)

    Patreon.com/thequestionshiphop questionshiphop.com Buy the Questions Hip-Hop Trivia Game Originally broadcast on September 16, 2020. Classic episode of The Questions Hip-Hop from the IG Live days, featuring DJ and producer Doo Wop. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram Doo Wop: Instagram

  41. 133

    IMAKEMADBEATS

    Patreon.com/thequestionshiphop questionshiphop.com Sean sits down with producer, Unapologetic. founder, and close friend IMAKEMADBEATS to talk about his latest album 'WANDS,' the journey of carving out a unique sound in the Memphis hip-hop scene, and the personal obstacles that have shaped the last few years of his life and career. Unapologetic. The Questions Hip-Hop: Instagram Sean Kantrowitz: Instagram IMAKEMADBEATS: Instagram

  42. 132

    Torae (Questions Classic)

    Patreon.com/thequestionshiphop questionshiphop.com Originally broadcast on August 10, 2020. Throwing it back to a classic episode from the IG Live days featuring Torae. The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter Torae: Instagram

  43. 131

    Making Illmatic - The Game 'The Documentary' w/ Psalm One & Optiks

    Patreon.com/thequestionshiphop questionshiphop.com Sean and MidaZ are joined by Psalm One and Optiks – who just dropped their collaborative album 'Is This a Safe Space?' – to put The Game's debut album 'The Documentary' under the Making Illmatic microscope. What are the 10 best songs on the album, and does editing help or hurt the LP? The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter MidaZ the BEAST: Instagram | Twitter Psalm One: Instagram | Twitter Optiks: Instagram | Twitter Psalm One & Optiks 'Is This a Safe Space?'

  44. 130

    Making Illmatic - RZA 'Bobby Digital In Stereo' w/ TzariZM

    Patreon.com/thequestionshiphop questionshiphop.com We're going digi! Sean and MidaZ are joined by return guest TzariZM to unpack the RZA's solo debut album, 'Bobby Digital In Stereo.' What are this album's 10 best songs, and does trimming it down help or hurt the record? The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter MidaZ the BEAST: Instagram | Twitter TzariZM: Instagram | Twitter MidaZ the BEAST and Tzarizm 'The Vivid Laser Eye Guy'

  45. 129

    The Chronicles of DOOM with S.H. "SKIZ" Fernando, Jr.

    Patreon.com/thequestionshiphop questionshiphop.com A conversation all about MF DOOM and 'The Chronicles of DOOM' – the new biography about the masked villain– with author S.H. "SKIZ" Fernando, Jr. Order the book: https://www.penguinrandomhouse.com/books/743088/the-chronicles-of-doom-by-sh-fernando-jr/ The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter

  46. 128

    Homeboy Sandman aka Visitor (Can't Knock the Shuffle Classic)

    Patreon.com/thequestionshiphop questionshiphop.com Original broadcast: November 4, 2020 Revisiting the appearance of Visitor (aka Homeboy Sandman) on Can't Knock the Shuffle, in which the artist and Sean explore the stories behind seven randomly-selected songs from his catalog: "Nuts" ['Nourishment (Second Helpings)', 2007] "Lightning Bolt, Lightning Rod" ('Actual Factual Pterodactyl,' 2008) "Trauma" ('Don't Feed the Monster', 2020) "Heaven Too" ('Hallways', 2014) "Always" ('Dusty', 2019) "Unforgettable" ('Subject: Matter', 2012) "Fat Belly" ('White Sands', 2014) The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter Homeboy Sandman: https://homeboysandman.bandcamp.com/

  47. 127

    MC Paul Barman (Can't Knock the Shuffle)

    Patreon.com/thequestionshiphop questionshiphop.com Many years in the making, Sean sits down with MC Paul Barman to explore the stories behind seven randomly-selected songs from his imaginatively incomparable catalog: "Circumcision Suite" (prod. Memory Man) ('Thought Balloon Mushroom Cloud,' 2009) "Blessings" (prod. Glen Brady) ('TECTONIC TEXTS,' yet-to-be-released) "Put Me On Your Do Not Call List" (prod. Michel Gondry) ('Blue Moon Kaboom,' 2017) "Anarchist Bookstore, Pt 2" (prod. MF DOOM) ('Paulellujah!', 2002) "Believe That" feat Open Mike Eagle (prod. MF DOOM) ('((echo chamber))', 2018) "Props" (prod. Questlove and James Poyser) ('Thought Balloon Mushroom Cloud,' 2009) "Mtv Get Off the Air, Part 2" feat Princess Superstar (prod. Prince Paul) ('It's Very Stimulating,' 2000) The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter MC Paul Barman: Instagram | Twitter | https://www.mcpaulbarman.com/

  48. 126

    Making Illmatic - Rjd2 'Deadringer' w/ Nate LeBlanc

    Patreon.com/thequestionshiphop questionshiphop.com Sean and MidaZ are joined by Dad Bod Rap Pod's Nate LeBlanc to put Rjd2's debut album 'Deadringer' under the Making Illmatic microscope. Which 10 songs will make the final cut? The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter MidaZ the BEAST: Instagram | Twitter Dad Bod Rap Pod: Instagram | Twitter MidaZ the BEAST and Tzarizm 'The Vivid Laser Eye Guy'

  49. 125

    Mic Geronimo (Questions Classic)

    Patreon.com/thequestionshiphop questionshiphop.com Originally broadcast on February 24, 2021. We revisit a classic episode from the IG Live days featuring Mic Geronimo. The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter Mic Geronimo: Instagram

  50. 124

    'Ol' Dirty Bastard: A Tale of Two Dirtys' w/ Jason Pollard and Young Dirty Bastard

    Patreon.com/thequestionshiphop questionshiphop.com We're uncovering the making of this summer's Ol' Dirty Bastard documentary 'Ol' Dirty Bastard: A Tale of Two Dirtys,' streaming now on A&E. Sean connects with the film's co-director Jason Pollard and one of the film's producers, Young Dirty Bastard (son of ODB). All audio clips from the film appear courtesy of A&E/Four Screens Management. The Questions Hip-Hop: Instagram | Twitter Sean Kantrowitz: Instagram | Twitter Ol' Dirty Bastard: Instagram Young Dirty Bastard: Instagram | Twitter Jason Pollard: Instagram | Twitter Four Screens Management: Instagram

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ABOUT THIS SHOW

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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The Questions Hip-Hop

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Frequently Asked Questions

How many episodes does The Questions Hip-Hop have?

The Questions Hip-Hop currently has 50 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is The Questions Hip-Hop about?

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. 

How often does The Questions Hip-Hop release new episodes?

The Questions Hip-Hop has 50 episodes. Check the episode list to see recent publication dates and frequency.

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The Questions Hip-Hop is created and hosted by The Questions Hip-Hop.
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