02.18.2026
Okayplayer’s 2x Webby Award-Winning Podcast The Almanac Of Rap Announces Season 4, Launching February 26th
Host Donwill Continues To Unearth Gems and Probe The Minds of Talented Guests, Including Bun B, Raekwon, Havoc, 9th Wonder, and Many More to Be Announced
Presented by Okayplayer, the Freewheeling, Deep-Diving Podcast About Hip-Hop History and Trends Airs Weekly On Thursdays

Critical Praise:
WEBBY AWARD WINNER 2025 – EXPERIMENTAL INNOVATION
WEBBY AWARD WINNER 2023 – BEST MUSIC PODCAST
The Announcement:
Donwill uses his deep love and vast musicological and historical knowledge of hip-hop to make his podcast, The Almanac Of Rap, a must-listen for fans looking to learn more about their favorite genre, straight from the mouths of legends and unsung heroes. The Tanya Morgan emcee prepares to resume his quest for knowledge, announcing The Almanac Of Rap Season 4, launching on February 26th.
Airing weekly on Thursdays, alternating between audio/video and audio-only episodes, the fourth season of the 2x Webby Award-winning, Okayplayer-presented podcast brings back the deep attention to detail and unexpected questions that have unearthed gems from a litany of hip-hop heavyweights. Host Donwill is a master of engaging conversation, using his experience as a rapper and lifelong love of music to dig into under-explored nooks and crannies, revealing a different side of his illustrious guests. Season 4 promises a new lineup of influential figures, including Bun B, Raekwon, Havoc, 9th Wonder & Reuben Vincent, LaRussell, Cupid, Mr. DJ, and more. Donwill’s list of guests extends beyond the realm of music: Season 4 also promises an interview with Moonlight and I’m A Virgo actor Jharrel Jerome.
“Season 4 is The Almanac of Rap’s most ambitious undertaking ever,” says Donwill. “We’re looking at dropping a new episode into your feed every week for a full year all while keeping the same high level of conversation and production value. This season we take a look at Outkast’s legacy, Rappers on Broadway, Line Dances, Buddhist Hip Hop and so much more. I love learning interesting fun facts and gaining knowledge directly from the mouths of some of the most interesting people in the rap world.”
Donwill keeps things fresh each week with a grab bag of recurring segments, designed to keep the conversation light and reveal tidbits about the guests’ lives and careers. Each episode starts with “The Ballistics,” in which Donwill delivers a little-known fact or controversial opinion that sets the tone for the interview that follows. “The Big Playback” is another regular segment, in which Don and his guest seek justice for an under-appreciated gem. Donwill occasionally breaks out other recurring segments, including “Type Beat,” in which he plays a producer a “type beat” inspired by their style, and “The Do Over,” a segment that allows guests to re-do an acceptance speech with the benefit of hindsight.
Season 4 brings the latest batch of episodes for the Okayplayer series, adding to a legacy that has already earned the program two Webby Awards. In 2023, AOR won the Webby for “Best Music Podcast,” while in 2025, the show won an award for “Experimental Innovation.” Past guests on the pod include Lupe Fiasco, A-Trak, MC Lyte, Rodney “Darkchild” Jerkins, Phonté, Lalah Hathaway, Wyatt Cenac, and many 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. Stay tuned for 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