Canadian Connections feat Shad

Canadian Connections feat Shad

From The Almanac of Rap by Donwill/Okayplayer

March 19, 2026 · 42 min · Season 4 · Episode 4

About this episode

Donwill interviews Canadian rapper Shad about his career and the hip-hop ecosystem in Canada.

📢 Special Announcement 📢 Want to join Donwill for a live recording of The Almanac of Rap in NYC?Click here to request an invite. (Limited capacity. Invite only.)On Air Fest, Soho House, and Okayplayer have joined forces for a special live episode of the Almanac of Rap featuring Regan Sommer McCoy, Chief Curator of the Mixtape Museum on March 24, 2026 at 5:30pm.Join Donwill and Regan at Ludlow House NYC for a conversation on hip-hop preservation, archival storytelling, and the hidden science behind mixtape culture. 📢 ### 📢 Juno Award-winning Canadian rapper and broadcaster Shad joins Donwill for a long-overdue conversation that spans music, media, and creative growth. From freestyling in London, Ontario to winning a Juno Award over Drake, Shad reflects on carving out a career in a country with a very different hip-hop ecosystem. Shad breaks down: His journey from freestyling in London to becoming a Juno Award-winning artist, and beating Drake in the process. Your Boy Tony Braxton and why artists should never “disrespect the music” Hosting Hip-Hop Evolution and interviewing icons like Dolly Parton and Norm Macdonald Follow Donwill for fun hip-hop history, cultural commentary…

People in this episode

Host: Donwill

Guest: Shad

Topics covered

  • hip-hop preservation
  • archival storytelling
  • mixtape culture
  • Canadian hip-hop
  • creative growth

Keywords

  • Shad
  • Donwill
  • hip-hop
  • Juno Award
  • mixtape culture
  • creative growth
  • interview

Mentioned in this episode

Organizations: Okayplayer, On Air Fest, Soho House

Products: K.I.S.S., Islands

Books & works: Hip-Hop Evolution

Places: NYC

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