3.19.2026
Donwill Chats With Shad in the Fourth Episode of The Almanac of Rap‘s Season 4
The New Episode of Okayplayer’s 2x Webby Award-Winning Podcast Discusses the Evolution of Canadian Rap, Touches on Blog Era History, and Shad’s Broadcasting Career
This Week’s Audio-Only Episode Benefits From Donwill and Shad’s Friendship and History of Collaboration, Notably “Rose Garden” by Shad & Tanya Morgan
Critical Praise:
WEBBY AWARD WINNER 2025 – EXPERIMENTAL INNOVATION
WEBBY AWARD WINNER 2023 – BEST MUSIC PODCAST
The Announcement:
Donwill’s deep curiosity, knowledge of hip-hop, and respect for the genre’s history makes The Almanac Of Rap one of the most intriguing podcasts around. The new, audio-only episode of the 2x Webby Award-winning podcast features Donwill’s conversation with Shad, the respected, Juno Award-winning rapper and Peabody-winning journalist (for his work on Hip-Hop Evolution).
Born in London, Ontario, Shad has spent nearly two decades as one of Canada’s favorite emcees, named the 2nd best Canadian rapper of all-time by the Canadian Broadcasting Corporation. He caught attention during the Blog Era and has continued to make music even as he has become a renowned broadcaster for the CBC. Donwill and Shad have a history of collaborating, most notably on the song “Rose Garden,” by Shad featuring Donwill and his Tanya Morgan groupmate Von Pea. The conversation on this episode of The Almanac Of Rap discusses Shad’s upbringing in London, halfway between Toronto and Detroit, exploring the evolution of Canadian rap from block party in the 70s to the rise of Drake in the 2010s (Shad relates a story about beating Drake for Rap Album of the Year at the 2011 Juno Awards). Beyond that, Shad and Donwill have some fun, revealing Shad’s dream festival headliners (he picks KRS-One, Alvvays, and “Weird Al” Yankovic), discussing his experience interview legends like Dolly Parton, Denzel Washington, and Paul Simon, and analyzing the state of rap media.
The fourth episode of Season 4 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.
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 9th Wonder & Reuben Vincent, and Seattle producer Jake One. As it continues, Season 4 promises an illustrious list of influential guests, including Bun B, Raekwon, Havoc, 9th Wonder & Reuben Vincent, Jharrel Jerome, LaRussell, Mr. DJ, and more.
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.
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.
Links:
official site | instagram | twitter | mixcloud
Connect with Donwill at Donwill.Me
Credit: Kaushik Kalidindi for Okayplayer