Donwill on The Almanac of Rap & The Art of the Interview

There's a moment in this conversation where Jay Ray marvels at Donwill asking Raekwon why the Purple Tape was purple. And Raekwon's answer — "they didn't have green" — says everything you need to know about why Donwill is built differently as an interviewer.

He's not chasing the headline. He's chasing the thing just outside the frame.

Donwill — rapper, DJ, Webby Award-winning podcaster, and one half of Tanya Morgan — sits down with DJ Sir Daniel and Jay Ray to talk about the craft behind The Almanac of Rap , his Okayplayer-produced podcast series. This conversation covers what it takes to interview artists the right way, how hip hop journalism lost the plot to the algorithm, and what it meant to step on a comedy stage as a rapper after hiding in plain sight behind the DJ booth.

Twenty years after Moonlighting , Donwill is still using history to build the future — and this episode shows exactly how he thinks. The Breakdown What started as a Twitch rant about LL Cool J became a Webby Award-winning podcast — Donwill breaks down how The Almanac of Rap grew from pandemic-era Twitch streams and a nudge from a friend into one of the most respected hip hop interview series running today.

The art of the question nobody else is asking — From the color of Raekwon's tape to the wellness routines of artists in their fifties, Donwill explains why good interviewing means finding the thing just outside the frame of what everyone already knows. "We're at the point where the clip is the whole thing" — A real conversation about hip hop journalism, algorithm dependency, and why the only honest answer to clip culture might be to let it burn. Michelle Buteau told him to rap — and he listened — The story of how DJing her tour led to an opening set, a new audience, and a reminder that leaning into the craft you sidelined can open new doors.

Rob Base was never a one-hit wonder — he was a legendary artist — In the wake of Rob Base's passing, the conversation shifts into a meditation on legacy, bridge songs, and what we actually mean when we reduce an artist to a single chart moment. Drop your thoughts in the reviews and let us know — what's the question nobody's ever asked your favorite rapper?

Find Donwill: 🎙 The Almanac of Rap 📰 Working Creative Weekly Substack 📸 @donwill on Instagram #QueuePoints, #BlackMusicHistory, #Donwill, #AlmanacOfRap, #HipHopJournalism, #TanyaMorgan, #HipHopPodcast