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
Oct. 7, 2026
The Answers: GoodWaves Festival Recap
Patreon.com/thequestionshiphop 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: sean@questionshiphop.com questionshiphop.com
Sept. 30, 2026
Propaganda
Patreon.com/thequestionshiphop 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: sean@questionshiphop.com
Sept. 23, 2026
Wildchild
Patreon.com/thequestionshiphop 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: sean@questionshiphop.com questionshi
Sept. 16, 2026
Danny Hastings
Patreon.com/thequestionshiphop 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: sean
Sept. 9, 2026
DJ Muggs
Patreon.com/thequestionshiphop 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: sean@questionshiphop.com questionshiphop.com
Aug. 26, 2026
Open Mike Eagle & Kenny Segal
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.c
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