Webby Award-Winning 'The Almanac of Rap' Podcast Announces Season 4, With Guests Bun B, Raekwon & Many More

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, which launched 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. 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 Beats,” 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.