
Show Notes
📢 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.
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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
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Instagram: @shadkmusic
Web: shadk.com
Music: K.I.S.S. + Islands
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com Learn more about your ad choices. Visit megaphone.fm/adchoices
More from The Almanac of Rap
What happens when one of hip-hop's most elusive albums becomes the subject of a Netflix documentary? RZA, the visionary producer, filmmaker, and founding architect of the Wu-Tang Clan, joins Donwill to discuss The Disciple: A Wu-Tang Fable, the new documentary chronicling the extraordinary journey of Once Upon a Time in Shaolin. Created as a single-copy work of art, the album became a multimillion-dollar cultural controversy after its sale to Martin Shkreli, raising questions about artistic ownership, creative freedom, and the value of music in the streaming era. RZA reflects on his relationship with producer Cilvaringz, the persistence that brought him into Wu-Tang's orbit, and the philosophical lessons behind a project whose legacy continues to evolve beyond its creators. The RZA breaks down:
Digable Planets helped redefine the possibilities of hip-hop in the early 1990s, blending jazz, funk, political consciousness, and a distinctly cosmic sensibility into a sound that resisted easy categorization. More than three decades later, Ishmael Butler (Butterfly) and Craig Irving (Doodlebug) join Donwill backstage at Brooklyn Bowl to revisit the group's unlikely beginnings, from three artists representing Seattle, Philadelphia, and Maryland to a Grammy-winning collective that made Brooklyn its creative home. They reflect on the success of Reachin' (A New Refutation of Time and Space), the complicated cultural politics of winning a Grammy in hip-hop's early years, and how their revolutionary upbringing informed the music and visual identity of Blowout Comb. Digable Planets break down:
Before Digable Planets helped redefine the sound of alternative hip-hop, Ladybug Mecca was a young artist absorbing Brazilian music, jazz, and the rhythms of her family's home. Three decades after Blowout Comb became a cornerstone of jazz-inflected hip-hop, the pioneering MC joins Donwill to discuss her latest chapter as a recipient of Harvard University's Nasir Jones Hip-Hop Fellowship. Her research traces the connections between hip-hop and Afro-Brazilian traditions, from Candomblé drumming to capoeira, challenging the idea that hip-hop simply arrived in Brazil rather than finding a culture already connected through rhythm, movement, and shared African ancestry.
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Before breaking became a global industry, and long before it became an Olympic event, Ken Swift was helping define what the dance could be. A longtime Rock Steady Crew member and one of the form’s most important second-generation B-boys, Swift joins Donwill on The Almanac of Rap to revisit the late-’70s and early-’80s New York scene where DJs, concrete floors, gymnasiums and neighborhood crews turned movement into a new language. He explains why “breakdancing” was always a media invention, how Rock Steady expanded across boroughs, and why early breaking was as much about character, rhythm and community as athleticism.