Critical Praise:
WEBBY AWARD WINNER 2025 – EXPERIMENTAL INNOVATION
WEBBY AWARD WINNER 2023 – BEST MUSIC PODCAST
The Announcement:
The winner of the 2025 Webby Award for Experimental Innovation, Donwill‘s podcast The Almanac of Rap is always game to try new things. Today, the 2x Webby Award-winning, Okayplayer-presented podcast reaches another milestone, debuting its first-ever live episode, with special guest Regan Sommer McCoy.
Recorded at Ludlow House on New York’s Lower East Side, in partnership with On Air Presents, the live-taped episode features a wide-ranging conversation between the Tanya Morgan rapper and the professional archivist and founder of the Mixtape Museum. The two discuss how cassette tapes transformed music sharing, the role of mixtapes before social media, and what we lose when alogrithms and streaming services dominate the playlist and mixtape landscape. McCoy makes special mention of mixtape legends, including Kid Capri, DJ Kay Slay, Justo Faison, and many others, regales anecdotes from the now-defunct Mixtape Awards, and praises influential mixes like the famous DOO WOP LIVE ’95. Concluding with a short Q&A, the conversation is a vital one, as Donwill and McCoy explain the importance of archiving and preserving hip-hop history, before essential media disappears into the digital ether.
This week’s episode is the 16th episode of The Almanac of Rap’s Season 4, which continues what Donwill calls “The Almanac of Rap’s most ambitious undertaking ever.” The podcast plans to drop a new episode every week for a whole year, alternating between audio/video and audio-only podcasts. A master of engaging conversation, Donwill uses his experience as a rapper (he is part of the group Tanya Morgan), and lifelong love of music to dig into under-explored nooks and crannies, revealing a different side of his illustrious guests. The veteran rapper keeps things fresh each week with recurring segments, including hot take-centric “The Ballistics” and “The Big Playback,” in which Donwill and his guest give flowers to an under-heralded or underrated gem.
In celebration of Black Music Month, and Donwill’s birthday last week, The Almanac of Rap launched Donwill’s Black Music Month Podcast Mixtape, a first-of-its-kind creator partnership initiative designed to spotlight independent music, culture, and conversation podcasts from across the community. Curated by Donwill and the rest of the AOR team, and presented in partnership with Castbox.fm, the new initiative shines a spotlight on the next generation of audio talent, amplifying shows that bring a new and entertaining perspective to shape music discourse. Among the list of recommended podcasts is Black People Love Paramore, the pod hosted by Sequoia Holmes, who recently guested on an episode of The Almanac of Rap. Find a full list of podcasts highlighted by this initiative below.
The Season 4 Premiere, featuring an interview with Cupid, the Line Dance King, reached the Top 10 of Apple Music’s Top Shows (Music) chart. Recent guests include Mr. DJ, the Grammy-winning OutKast producer, Havoc of Mobb Deep, Bun B, Jharrel Jerome, 9th Wonder & Reuben Vincent, Masta Ace, and Seattle producer Jake One. As it continues, Season 4 promises an illustrious list of influential guests, including Flying Lotus, LaRussell, and more.
Listen to the episode HERE, or wherever you get your podcasts
Watch the teaser for The Almanac of Rap Season 4 HERE
List of Podcasts Included on Donwill’s Black Music Month Podcast Mixtape:
The Almanac of Rap wouldn’t exist but for the passion and curiosity of host Donwill. Born in Cincinnati before re-locating to Brooklyn, Donwill entered the music industry as one-third of hip-hop group Tanya Morgan, with his creative partners Von Pea and Ilyas. The group is best known for the 2009 album Brooklynati, now hailed as an underground classic, but performing music is only part of Donwill’s story. He is a prolific DJ, holding court at many of Brooklyn’s hottest nightlife establishments and touring as the DJ for comedian Michelle Buteau. His music production work has earned him credits on Emmy-winning programs like Last Week Tonight with John Oliver, and produced theme music for award-winning podcasts like Slow Burn (Slate), Another Round (Buzzfeed), and #Adulting (WNYC).
Donwill brings that unique experience, curiosity, and dedication to his craft to each episode of The Almanac Of Rap. Don’t miss the rest of Season 4, which promises to be one of the most wide-ranging and entertaining seasons of the award-winning podcast to date.
Listen to The Almanac Of Rap wherever you get your podcasts:
Credit: Kaushik Kalidindi for Okayplayer
Please contact Michelle or Kevin for more info.
The Background:
About the Almanac of Rap:
The Almanac of Rap is a weekly show hosted by Donwill that examines the origins of specific trends in hip hop and their impact over time and it’s way more fun than that description makes it sound. Each week, Donwill asks a question, presents a theory, and finds a guest to come to some sort of consensus about it. Simply put, it’s a show about rap by a rapper who loves rap music.
About Donwill:
Pulling from the crates of the blog era and the extremely online, Donwill is a certified rap encyclopedia — err, rather, a rap almanac. So then, it’s only right he’s the host of Almanac of Rap, a Webby Award-winning Okayplayer-produced series that combines the smartest, If You Know You Know™ rap conversations with deep-in-the-weeds fandom and sharp satirical humor. It’s all curated by Donwill, a former blogger who’s traded book recommendations with Lupe Fiasco and rapped with Drake as a member of the duo Tanya Morgan. If he’s not the most interesting rapper alive, he could do a hell of an interview with them. In an age of less-than-ethical streamers and scandal-chasing “interviewers,” Donwill employs a workmanlike approach to the art of journalism, taking at least a week to research each episode of his show. It’s appreciation as much as attention to craft. It’s also why his podcast stands as a show by and for the culture. And that’s probably because it is the culture. More specifically speaking, Donwill is the culture. Having written for The Village Voice as a reporter, traded bars with Drake, and interviewed rap titans like Lupe Fiasco, Donwill is the coach, the player, and the opponent — the journalist and the source. In other words, he’s the rapper-turned-podcaster we deserve.
Credit: Kaushik Kalidindi for Okayplayer
Links:
Donwill: official site | instagram | twitter | mixcloud
Connect with Donwill at Donwill.Me