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Jay is the host of the longest-running hip-hop radio show ever, The Underground Railroad on New York City station WBAI. He’s had the show since 1991, and helped create the template of what an underground mix show is supposed to be. He also had arguably first hip-hop blog way back in 1997 with

But Jay is perhaps best known as a pioneering video blogger. His video series Ill Doctrine, which deals with hip-hop, politics, cats, and lots more, has garnered millions of views, and many of the entries have gone viral, including now-classic video essays like “How To Tell Someone They Sound Racist.”

Tracks featured in this episode:

  1. Jay Smooth, “Internet Beef Rap”
  2. Jay Smooth, “Internet Beef Rap”
  3. Wu-Tang Clan, “Wu-Tang: 7th Chamber - Part II - Conclusion”
  4. Wu-Tang Clan, “Protect Ya Neck”
  5. Wu-Tang Clan - After The Laughter Comes Tears
  6. Dj Stretch Armstrong & Bobbito Live Radio Show 28 October 1993
  7. A Tribe Called Quest & Consequence Freestyle (Underground Railroad)
  8. The Underground Railroad December 1993 WBAI 99.5fm NYC
  9. Cassette Culture with Stretch Armstrong: The Latin Rascals, Dec. 1985, Kiss-FM NYC
  10. Jay-Z & Natural Elements - Underground Railroad Freestyle
  11. Organized Konfusion - Underground Railroad Freestyle
  12. Black Thought & Mr. Voodoo on The Underground Railroad
  13. Democracy Now! Daily Show Mon. May 8, 2017
  14. Creative Unity Collective (10-4-08) Part 1
  15. Riley Woollen ‘15 And Ed Randolph | A Memorable Day
  16. Gylan Kain, “Silly Shit”
  17. KMD, “What a Nigga Know?”
  18. Willie Perdoma — Nigger Reecan Blues on Def Jam Poetry
  19. This American Life 550: Three Miles
  20. Maria Bamford: Old Baby | Official Trailer [HD] | Netflix
  21. Radiohead, “Nude”
  22. Jay Smooth, “Why are we such suckers for the “beauty” of war?”
  23. Common Market, “Tobacco Road (Instrumental)”
  24. Jay Smooth, “Trump’s America: This is What Happens Now”
  25. Jay Smooth, “Trump’s America: This is What Happens Now”
  26. Jay Smooth, “Yes, Hip-Hop Is Dead (For You)”
  27. Jay Smooth, “Barack Obama and Tolerance Fatigue”
  28. Jay Smooth, “Why Is Every Hip-Hop Debate So Annoying?”
  29. Jay Smooth, “How To Tell Someone They Sound Racist”
  30. TEDxHampshireCollege - Jay Smooth - How I Learned to Stop Worrying and Love Discussing Race
  31. Jay Smooth - Ill Doctrine, XOXO Festival (2013)
  32. Colorlines News, “Deconstructing ‘White Privilege II’”
  33. Colorlines News, “Deconstructing ‘White Privilege II’”
  34. Colorlines News, “Deconstructing ‘White Privilege II’”
  35. Colorlines News, “Deconstructing ‘White Privilege II’”
  36. ‘I’m actually black’ responds Jay Smooth
  37. The Underground Railroad, “Jay Smooth, mic wrecker extraordinaire”
  38. Jay Smooth, “If Bill O’Reilly Was A Rapper”
  39. Jay Smooth, “If Bill O’Reilly Was A Rapper”
  40. Jay Smooth, “Jay-Z “Glory” (Mitt Romney Remix)”
  41. Jay Smooth, “ill Doctrine Dipset Anthem”
  42. Scienz of Life, “WBAI freestyle”
  43. The Underground Railroad, “Wu Tang Clan 1993”
  44. Nas, “Sly Fox”
  45. Nas interview + Sly Fox Live COLBERT REPORT SHOW 2008

Show notes:

  1. Dj Stretch Armstrong & Bobbito Live Radio Show 28 October 1993
  2. The Underground Railroad December 1993 WBAI 99.5fm NYC
  3. Village Voice, “Mark Drake’s Words”
  4. Village Voice, “Q&A: Drake On Battle Rappers, A$AP Rocky, And His Five-Figure Bet With Nelly”
  5. The Virginian-Pilot, “Virginia Beach woman’s Bible was overlooked by ‘Antiques Roadshow,’ but now lives at the Smithsonian”
  6. The Obama Deception: Why Cornel West Went Ballistic
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