Shaggy Guests on Donwill's The Almanac of Rap

07-04-2026

(Audible Treats) Donwill hosts guests of all statures and eras on his 2x Webby Award-winning podcast The Almanac of Rap, using his love of music to guide his probing, yet fun-loving questions.

On this week's episode, Donwill welcomes international dancehall superstar Shaggy, giving the artist an opportunity to discuss every facet of his wide-ranging career. Known for his number one hits "It Wasn't Me" and "Angel," and the dancehall classic "Boombastic," Shaggy has decades worth of stories from the highest echelons of the music industry, from his days leading dancehall onto the pop charts to his current status as an elder statesman and adventurous collaborator.

The Jamaican-American artist is generous with stories, revealing secrets behind his big hits (for example, Rayvon replaced a different artist on "It Wasn't Me" after the original artist became a born-again Christian), and recalls meeting Michael Jackson at a benefit concert ("That could have been one of my songs," said Michael of "It Wasn't Me"). Later in the episode, Shaggy discusses his creative partnership with Sting, which has spanned an album, a world tour, and now, a Broadway musical, and discusses his relationship with his son, the rapper Robb Bank$. Donwill also allows Shaggy to correct the historical record, encouraging him to give the Grammy acceptance speech that he never got a chance to give, and on "The Big Playback," reveal which songs from his catalog he thought should have been much bigger hits. The wide-ranging conversation finds Shaggy proud of his mainstream success ("I would sell out in two minutes," he says) and displaying the charming personality and adventurous spirit that has allowed him to thrive for decades.

This week's episode is the 19th 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 alst 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 Flying Lotus, Raekwon, Havoc of Mobb Deep, Bun B, Jharrel Jerome, 9th Wonder & Reuben Vincent, Masta Ace, and many others. As it continues, Season 4 promises an illustrious list of influential guests, including Chika, LaRussell, La Reezy, and more. Most recently, for the show's 18th episode, Donwill interviewed Awon and Joe Miles of "The Other Guys" about running an independent rap label.