02.26.2026
Line Dance Legend Cupid Joins Donwill For “Black Line Dance Power Rankings,” the Debut Episode of The Almanac of Rap‘s Season 4
The New Episode of Okayplayer’s 2x Webby Award-Winning Podcast Discusses Cupid’s Long Career and the Rich History of Black Line Dancing
This Week’s Episode Features Lively Discussion About the Top 5 Black Line Dance Songs, the Role of YouTube Instructors and DJs in Spreading Line Dances, and the Story of Cupid’s Hits Like “Flex” and “Cupid Shuffle”
Critical Praise:
WEBBY AWARD WINNER 2025 – EXPERIMENTAL INNOVATION
WEBBY AWARD WINNER 2023 – BEST MUSIC PODCAST
The Announcement:
Donwill‘s 2x Webby Award-winning podcast The Almanac Of Rap is powered by the host’s curiosity and depth of knowledge, exploring hip-hop trends and history with panache and wry humor. Today, the Okayplayer-presented podcast returns for its Fourth Season, welcoming Cupid, The Line Dance King himself, behind such immortal hits as “The Cupid Shuffle” and “Flex,” as the season’s first guest.
In the episode, titled “Black Line Dance Power Rankings,” Donwill sets the tone with his regular “The Ballistics” segment, ranking his list of the top five line dance songs of all-time. After Donwill says his piece, he brings in Cupid to discuss his long career and the role of line dances in Black culture. The two artists debate whether DJs or YouTube line dance instructors are more important when breaking a song, discuss how Cupid’s hit “Flex” blew up during COVID (when one would think the lack of gatherings would prevent new dances from gaining momentum), and joke about how Cupid’s status as The Line Dance King has earned him the attention of aunties across the nation. Donwill and Cupid also discuss Cupid’s line dance “Big 3” (DJ Casper, Cupid, and Big Moochie), extol the greatness of underrated, Static Major & Timbaland-helmed R&B classic Playa’s Cheers 2 U, and explain why Chief Keef’s “Faneto” would be a great line dance song.The first episode of Season 4 kicks off 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. Season 4 promises an illustrious list of influential guests, including Bun B, Raekwon, Havoc, 9th Wonder & Reuben Vincent, Jharrel Jerome, LaRussell, Cupid, Mr. DJ, and more.
Credit: Trigger Bowden
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