Catalog
Episodes
Rapping Actors feat Jharrel JeromeJun 4, 2026 · 58 minThis week on The Almanac of Rap, Donwill sits down with Emmy Award-winning actor and recording artist Jharrel Jerome for a conversation about hip-hop, storytelling, acting, and the journey toward embracing music publicly.
Known for acclaimed performances in Moonlight, When They See Us, and Unstoppable, Jharrel opens up about why rap was actually his first love long before acting entered the picture. From rapping for entry into Bronx basketball games as a kid to studying Eminem lyrics obsessively, Jerome reflects on how storytelling through rhyme shaped the creative foundation of his entire career. Jharrel breaks down:
How his upbringing in the Bronx continues to influence his artistic identity.
Blending cinema with rap visuals for his four “Pack” EP projects
How artists like Frank Ocean, Kendrick Lamar, Fred the Godson, and Action Bronson soundtracked different stages of Jerome’s acting career.
The emotional toll of filming When They See Us, physically transforming for Unstoppable, and his desire to help bring lyric-driven hip-hop back to the forefront.
🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Jharrel Jerome
Instagram: @jharreljerome
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices- Rock n Rap feat Sequoia HolmesMay 28, 2026 · 55 minThis week on The Almanac of Rap, Donwill sits down with culture critic, SiriusXM host, and Black People Love Paramore creator Sequoia Holmes for a hilarious and insightful conversation about Black alternative culture, pop punk nostalgia, Disney Channel, Nickelodeon, and the unexpected intersections between rap and rock music.
Sequoia reflects on growing up as a Black Paramore fan during the emo era, why bands like Paramore, Fall Out Boy, Coldplay, and Panic! at the Disco resonated with Black listeners, and how her podcast became a space to unpack the “common and uncommon interests” of Black audiences online. The conversation also explores the evolution of “alternative” music, the decline of rock bands in the streaming era, and how modern artists blur genre lines between rap, pop, punk, and internet culture.
Don and Sequoia debate Miley Cyrus’ rap era, revisit iconic Nickelodeon and Disney Channel theme songs, discuss why shows like All That, Cousin Skeeter, and That’s So Raven were secretly foundational Black cultural experiences, and break down artists like Rico Nasty, Tierra Whack, Lil Uzi Vert, and Teezo Touchdown through the lens of alternative hip-hop. Sequoia breaks down:
Why Black audiences connected deeply with Paramore
Nickelodeon’s hidden influence on Black music culture
Miley Cyrus’ rap era revisited years later
The blurred lines between rap, punk, and alternative music
🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Sequoia Holms
Instagram: @bplppod
Black People Love Paramore: Podcast
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- The Rapper’s Rapper feat GrafhMay 21, 2026 · 1 hr 12 minThis week on The Almanac of Rap, Donwill sits down with Queens lyricist Grafh to talk about battle rap, mixtape culture, lyricism, and surviving the music industry on his own terms.
Grafh reflects on discovering rap through Nas’ Illmatic, studying rhyme patterns with a dictionary, and developing the intricate writing style that would later make him a respected “rapper’s rapper.” The conversation explores the difference between writing a great verse versus crafting a great song, ghostwriting for major artists, and learning song structure from collaborators like Kanye West and 88-Keys.
Grafh also shares stories about battling rappers in studios before the modern battle rap era, getting co-signed by the late DJ Kay Slay, working with Busta Rhymes, signing to Roc-A-Fella Records during the label’s final years, and eventually finding financial freedom through today’s underground rap ecosystem. Grafh breaks down:
The art of lyrical wordplay
The real business behind mixtape-era rap
Busta Rhymes, Kay Slay & Roc-A-Fella
Why underground rap is thriving independently
🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Grafh:
Instagram: @grafh
Website: artbygrafh.com
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Graffiti Rock feat Michael HolmanMay 14, 2026 · 55 minBefore hip-hop became a billion-dollar industry, it was a living culture being built in clubs, parks, train yards, and downtown art spaces across New York City.
This week on The Almanac of Rap, Donwill sits down with writer, filmmaker, musician, and Graffiti Rock creator Michael Holman to unpack the early days of hip-hop culture and the movement that brought its four elements to a national audience for the first time.
Holman reflects on working alongside pioneers like Fab Five Freddy, Jean-Michel Basquiat, Martha Cooper, and Henry Chalfant, while helping shape the downtown New York scene that amplified breaking, graffiti, DJing, and rap beyond the Bronx. The conversation explores the creation of Graffiti Rock, the commercialization of rap versus hip-hop culture, and why graffiti writers, breakers, and DJs were eventually pushed to the margins as rap became the industry focus. Michael Holman breaks down:
The untold origins of Graffiti Rock
Fab Five Freddy, and downtown hip-hop culture
Basquiat’s band Grey
Why rap and hip-hop are not the same thing
The role of Puerto Rican breakers in evolving b-boy culture
How downtown clubs accidentally helped formalize the “four elements” of hip-hop as we know them today
🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.Substack: New Music TuesdaysInstagram/Threads: @donwillMixcloud: DonwillWebsite: Donwill.me
Follow Michael Holman:
Instagram: @michaelholman101
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- The Chef feat RaekwonMay 7, 2026 · 42 minWhat if the “Purple Tape” was green?
Does Polo Ralph Lauren and Clarks’ Wallabees owe Wu-Tang residuals for teaching an entire generation how to rock each brand?
And how did Raekwon navigate dropping his solo album AFTER standout projects from both Meth and Ghost?
This week on the Almanac of Rap, Donwill sits down with Wu-Tang Clan founding member and future Rock & Roll Hall of Fame inductee, Raekwon. Don and Rae discuss his influential solo debut album "Only Built for Cuban Linx," its iconic purple tape marketing, and the challenges of producing its sequel. Raekwon breaks down:
The importance of authenticity, hard work, and expanding the Wu-Tang universe through his music.
His impact on fashion, including popularizing the Polo Snow Beach jacket and various collaborations that support emerging artists.
His current goals of educating youth and maintaining artistic integrity.
🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Raekwon:
Instagram: raekwon
Web: www.officialraekwon.com/
Linktr.ee: @RaekwonTheChef
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- AOR Mini - Michael, Tara Chase and StaHHRMay 5, 2026 · 10 minOn this week’s Almanac of Rap mini-sode, Donwill hits the hotline and the callers come through with takes on the new Michael Jackson biopic, favorite women in hip-hop, and an unexpectedly serious debate about who has the best hair in rap (yes, there’s a running list). Along the way, listeners put Don onto hidden gems old and new, proving once again that rap’s best discoveries often come from the community. Equal parts mailbag, music nerd-out, and comedy hour; it’s another fun one from the Almanac hotline.
Check out:
staHHr - Get Right
Tara Chase- Autonomy (1997)
📞 Got a burning hip-hop question? A thought about a past episode? A gushing compliment that you didn’t want to leave on the Youtube channel?
Call us up at 1-877-DONWILL (366-9455) and leave a message. Make sure to leave your name because we just might use your message on a future episode. (Remember calls can only be 1 minute long.)
Next topic: ☎️ Put Don onto some dope sh!t — old music, forgotten films, underrated books, great art… share something good.
Bonus: Don is still on tour with Michelle Buteau, catch a show if he’s hitting your city, tickets here.
May 6 - Los Angeles - Dolby Theater w/ Michelle Buteau
May 8 - Las Vegas - The Palazzo Theater w/ Michelle Buteau
May 15 - Atlanta - Tabernacle w/ Michelle Buteau
May 16 - New York City - The Beacon Theater w/ Michelle Buteau
May 17 - New York City - The Beacon Theater w/ Michelle Buteau
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Big Ohio Status feat BlueprintApr 30, 2026 · 1 hr 3 minIn this episode of The Almanac of Rap, Donwill sits down with Blueprint, rapper, producer, author, founder of Weightless Records, and co-host of the Super Duty Tough Work podcast. The two Ohio natives dive into Blueprint’s creative process, from choosing between producing and rapping to knowing when it’s time to make an album. Blueprint shares the journey of the independent grind, the evolution of Midwest hip-hop scenes, and the legacy of Scribble Jam as a cultural hub for MCs, DJs, and artists. Blueprint breaks down:
His journey building an indie label from the ground up
The essential game for artists navigating today’s music industry.
Why independent success starts with ownership, not permission
🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Blueprint:
Instagram: printmatic
Linktr.ee: printmatic Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- AOR Mini: MailbagApr 28, 2026 · 15 minIn today’s Almanac of Rap minisode, Donwill takes a moment in between tour stops to ask listeners about formative hip hop moments, the four (or five) pillars of hip hop, and he takes a moment to share two standout emcees Salimata and Kelly Moonstone.
Join the conversation by calling 1-877-DONWILL (366-9455).
You got a burning hip hop question? A comment about a past episode? A gushing compliment that you didn’t want to leave on the Youtube channel? Call us up and leave a message!And make sure to leave your name because we just might use your message on a future episode
Next topic: ☎️ the Michael Jackson movie…Are you going to see it? Have you seen it? Thoughts? Call Don and let him know.
Also, Donwill is still on tour with Michelle Buteau and if you see your city you can get tickets here.
May 1 - Oakland - Fox Theater w/ Michelle Buteau
May 6 - Los Angeles - Dolby Theater w/ Michelle Buteau
May 8 - Las Vegas - The Palazzo Theater w/ Michelle Buteau
May 15 - Atlanta - Tabernacle w/ Michelle Buteau
May 16 - New York City - The Beacon Theater w/ Michelle Buteau
May 17 - New York City - The Beacon Theater w/ Michelle Buteau
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- The Dungeon Family Tree feat Mr. DJApr 23, 2026 · 1 hr 4 minGrammy-winning producer and Outkast dj, Mr. DJ shares his journey from discovering djing in Texas to becoming a key figure in Atlanta's hip hop scene. This week on the Almanac of Rap, he and Donwill discuss his early work with Organized Noise, his role in producing iconic Outkast tracks like "Miss Jackson" and "B.O.B.", and the formation of Earth Tone 3. Mr. DJ shares the evolution of Outkast's sound, the cultural significance of Southern hip hop, and the influence of the Dungeon Family, including Rico Wade. He also reflects on the challenges of gaining respect for Southern artists and the creative process behind landmark songs such as "Bombs Over Baghdad." Mr. DJ breaks down:
Outkast getting booed at The Source Awards and Andre 3000’s iconic line “The South got something to say”
The significance of his cousin, Rico Wade, founder of the Dungeon Family
His recent venture as a solo artist with the album "Beats, Vibes, and Verses," featuring collaborations with artists like Big K.R.I.T. and Killer Mike.
🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Mr. DJ:
Instagram: iammrdj
Caddillife: ffm.to
Web: https://iammrdj.com/
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- AOR Mini: Underrated LPsApr 21, 2026 · 12 minIn today’s Almanac of Rap minisode, Donwill takes a moment in between tour stops to ask listeners what albums (or artists) are CRIMINALLY UNDERRATED. Who did we miss? Join the conversation by calling 1-877-DONWILL (366-9455).
You got a burning hip hop question? A comment about a past episode? A gushing compliment that you didn’t want to leave on the Youtube channel? Call us up and leave a message!And make sure to leave your name because we just might use your message on a future episode.
Next topic: ☎️ Who are your favorite women in hip hop??! Call Donwill and tell him your favorite groups, albums, performances and contributors to the culture.
Also, he's still on tour with Michelle Buteau and if you see your city you can get tickets here.
Apr 24 - Kansas City - Midland Theatre w/ Michelle Buteau
Apr 25 - St. Louis - The Pageant w/ Michelle Buteau
May 1 - Oakland - Fox Theater w/ Michelle Buteau
May 6 - Los Angeles - Dolby Theater w/ Michelle Buteau
May 8 - Las Vegas - The Palazzo Theater w/ Michelle Buteau
May 15 - Atlanta - Tabernacle w/ Michelle Buteau
May 16 - New York City - The Beacon Theater w/ Michelle Buteau
May 17 - New York City - The Beacon Theater w/ Michelle Buteau
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- The Falling Season feat Masta AceApr 16, 2026 · 35 min🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
What happens when a legendary MC takes hip-hop from the booth to the stage?
This week on The Almanac of Rap, Donwill sits down with Masta Ace to explore the intersection of hip-hop and musical theater and what it takes to bring rap storytelling to Broadway.
From his days in the Juice Crew to building a decades-long career as one of rap’s most respected lyricists, Masta Ace reflects on longevity, reinvention, and why he still feels like he has something to prove. Masta Ace discusses:
His ambitious adaptation of The Falling Season into a stage play
Unpacking the creative process, the discipline of rewriting, and how rap lyrics must evolve when they’re used to push a narrative forward on stage.
Plus: a deep dive into hip-hop musicals from Hamilton to underground theater and why Broadway is still catching up to the culture.
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Masta Ace:
Instagram: mastaacepics
Facebook: Masta Ace
Web: www.mastaace.com
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Infamous to Infinite feat HavocApr 9, 2026 · 45 min🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️
Few sounds in hip-hop are as poignant, or as influential, as the gritty production that came out of Queensbridge in the ‘90s. This week on The Almanac of Rap, Donwill sits down with Havoc, producer, rapper, and one half of Mobb Deep, to break down the sonic blueprint that helped define East Coast hip-hop.
From crafting signature beats behind classics like The Infamous to shaping the identity of Queensbridge rap alongside Prodigy, Havoc reflects on his production style, creative process, and the raw realities that informed their music. The conversation dives into sampling, drum programming, and how limitation often led to innovation in early hip-hop production. Havoc breaks down:
Legacy, longevity, and how the Mobb Deep sound continues to influence generations of producers and artists today from underground purists to mainstream trap.
The making of Mobb Deep’s signature dark sound.
Havoc’s production techniques and sampling approach.
Producers rappers that he would solicit beats vs rhymes from today.
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Havoc:
Instagram: mobbdeephavoc
Linktr.ee: Havoc
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- The Buddha and The Beat feat Born IApr 2, 2026 · 36 minReligion has always had a place in hip-hop, from ‘god-body’ flows to references of the “third eye” and quoting Surahs; but what happens when you sit down with an actual Buddhist rapper?
This week on The Almanac of Rap, Donwill is joined by rapper, author, and practitioner Born I to explore the long-standing (and often misunderstood) relationship between Buddhism and hip-hop culture. From references to “Buddha” in rap lyrics to deeper conversations around mindfulness, suffering, and self-compassion, this episode separates fact from folklore. Born I will break down:
Key Buddhist concepts like the Four Noble Truths, Dharma, and mantras
His own journey navigating hip-hop, electronic music, and spiritual practice
How artists use music as testimony, how hooks can function like mantras, and why hip-hop’s connection to Buddhism runs deeper than weed references and fashion logos.
Plus, Jay-Z, Kendrick Lamar, Mac Miller, and Childish Gambino lyrics get put under the microscope…are they actually tapping into Buddhist philosophy, or just vibing? (You be the judge.)
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Born I
Instagram: bornimusic
Web: bornimusic.com
Soundcloud: bornimusic
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Rap Snacks feat Bun BMar 26, 2026 · 1 hr 31 minThis week on The Almanac of Rap, Donwill is joined by hip-hop legend Bun B for a deep conversation on the evolution of Southern rap, the cultural impact of UGK, and how Texas carved out its own lane in hip-hop history. From Port Arthur to global stages, Bun B reflects on building UGK alongside Pimp C, navigating regional bias in the early days of hip-hop, and the slow but undeniable rise of the South to dominance. The conversation explores how independent hustle, local scenes, and sonic innovation helped Southern artists shift the industry’s center of gravity. Bun B breaks down:
How UGK helped define the Southern rap sound
The South’s fight for respect in early hip-hop
Texas rap culture and independent grind
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Bun B
Instagram: bunb
Tik Tok: bun_b1
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Canadian Connections feat ShadMar 19, 2026 · 42 min📢 Special Announcement 📢
Want to join Donwill for a live recording of The Almanac of Rap in NYC?Click here to request an invite. (Limited capacity. Invite only.)On Air Fest, Soho House, and Okayplayer have joined forces for a special live episode of the Almanac of Rap featuring Regan Sommer McCoy, Chief Curator of the Mixtape Museum on March 24, 2026 at 5:30pm.Join Donwill and Regan at Ludlow House NYC for a conversation on hip-hop preservation, archival storytelling, and the hidden science behind mixtape culture.
📢 ### 📢
Juno Award-winning Canadian rapper and broadcaster Shad joins Donwill for a long-overdue conversation that spans music, media, and creative growth. From freestyling in London, Ontario to winning a Juno Award over Drake, Shad reflects on carving out a career in a country with a very different hip-hop ecosystem. Shad breaks down:
His journey from freestyling in London to becoming a Juno Award-winning artist, and beating Drake in the process.
Your Boy Tony Braxton and why artists should never “disrespect the music”
Hosting Hip-Hop Evolution and interviewing icons like Dolly Parton and Norm Macdonald
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Shad
Instagram: @shadkmusic
Web: shadk.com
Music: K.I.S.S. + Islands
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com
Learn more about your ad choices. Visit megaphone.fm/adchoices
- The Two First Namers Club feat Reuben Vincent & 9th WonderMar 12, 2026 · 1 hr 25 minIn this episode of The Almanac of Rap, Donwill sits down with 9th Wonder, Grammy-winning producer, Jamla Records founder, Little Brother co-founder, and college professor, alongside rising North Carolina MC Reuben Vincent, one of the sharpest young lyricists in the game. Together they unpack:
The legacy of North Carolina hip-hop9th Wonder’s journey from producer to professor
Discovering Reuben Vincent at just 13 years old
Why using your government name in rap is basically a skill badge
Jamla Records and artist development in the streaming era
Education, mentorship, and preserving hip-hop history
How the internet changed artist relationships foreverThe making of their joint album Welcome Home
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow 9th Wonder:
Instagram: @9thwonder
Twitter/X: @9thwonder
Jamla Records: @jamlarecords
Follow Reuben Vincent:
Instagram: @reubenvincent
YouTube: @reubenvincent
Album: Welcome Home
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Type Beats feat Jake OneMar 5, 2026 · 33 minWhat does a beat sound like when it… sounds expensive? In this episode of The Almanac of Rap, Donwill sits down with legendary Seattle producer Jake One, the mind behind records for MF DOOM, Freddie Gibbs, Rick Ross, J. Cole, Freeway, Snoop Dogg, Brother Ali, Tuxedo, and even the iconic John Cena theme. Together they unpack one of the most important shifts in modern hip-hop production: the rise of type beats. Jake One breaks down:
What “type beats” actually are and how they changed the music economy
The BeatStars marketplace and the viral story behind Old Town Road
The difference between analog era producers and FruityLoops generation producers
Speed-running beats, drum kits, and the gamification of music production
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
Follow Jake One:
Instagram: jakeuno
Web: snarejordan.com
Bancamp: Jake One
Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Black Line Dance Power Rankings feat CupidFeb 26, 2026 · 48 minWhat do the Cupid Shuffle, Electric Slide, Cha Cha Slide, Swag Surf, and The Wobble all have in common? They move the culture. In this episode of The Almanac of Rap, Donwill sits down with Cupid, six-time platinum recording artist, Guinness World Record holder, and officially proclaimed “Line Dance King of the World.” If you’ve ever heard “Down, down, do your dance…” at a wedding, cookout, HBCU homecoming, or kickback, this one’s for you.From selling CDs out of his trunk in Louisiana to global tours across Saudi Arabia, Qatar, Djibouti, and beyond, Cupid breaks down:
The origin story of the Cupid Shuffle
Line dance beef (yes, it’s real)
Why drill music needs a line dance
Follow Donwill for fun hip-hop history, cultural commentary, and more.
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Created and hosted by two time Webby Award-winning host Donwill, The Almanac of Rap is produced by Okayplayer, a division of AREYA MEDIA Inc. Originally launched in 1999, Okayplayer is the original progressive music site and maintains its position as the premier digital destination for music and culture connoisseurs worldwide. Find exclusive Okayplayer merch, tees and limited releases at https://shop.okayplayer.com.
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- Art Official Intelligence feat Lupe FiascoOct 18, 2024 · 1 hr 16 minFor our season finale we talk to Lupe Fiasco about his concept albums, his work with MIT, Yale and Google and history in martial arts. We also talk about the many supergroups he’s started and get a status update on if they are active or dormant.
Lupe Fiasco is a grammy award winning rapper who has found a voice outside the booth by teaching classes about rap at MIT and working with Google’s large language model to develop a TextFX, an AI tool made specifically for writers.
For more information visit:
Lupe Fiasco: LupeFiasco.com
Donwill: Donwill.me or donwill.substack.com
Okayplayer: Okayplayer.com
The Almanac of Rap is executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris.Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- Artist Profile: Homeboy SandmanOct 10, 2024 · 29 minThis week’s guest is Homeboy Sandman and we talk about him not being on social media, getting love from mainstream artists, his creative process and his upcoming tour.
Homeboy Sandman is a Brooklyn based MC with a deep discography and rich history in the New York music scene.
For more information visit:
Homeboy Sandman: patreon.com/homeboysandman
Donwill: Donwill.me
Okayplayer: Okayplayer.com
The Almanac of Rap is executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris. Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- Artist Profile: Cory GunzOct 3, 2024 · 43 minThis week’s guest is Cory Gunz and we talk about him being mentored by Nick Cannon, Godfathered by Shaq, working with Lil Wayne and being raised by Peter Gunz. We also discuss his current crop of releases and his new crew, The Militia.
For more information visit:
Corey Gunz: instagram.com/CoryGunz
Donwill: Donwill.me
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris.Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- Hip Hop Cartoons & Pioneer Power feat MC LyteSep 26, 2024 · 50 minThis week we talk to MC Lyte about her career and the way that she’s pioneered in music, fashion and more. We also do a quick study of the history of rappers with cartoons and pitch a few ideas for new cartoons that feature rappers.
MC Lyte is rapper, DJ, actor and TV producer who’s been a part of some of culture's biggest moments.
For more information visit:
MC Lyte: mclytenow.com
Donwill: Donwill.me
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris.Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- Artist Profile: CavalierSep 19, 2024 · 50 minThis week we talk to Cavalier about releasing multiple albums, ‘legal weed’, moving to New Orleans and much, much more.
Cavalier is a fiercely independent Brooklyn born artist whose new album Different Type Time has achieved critical acclaim.
For more information visit:
Cavalier: cavwins.com
Donwill: Donwill.substack.com
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris.Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- Internet Rappers feat. Von PeaSep 12, 2024 · 27 minThis week we talked to Von Pea about Internet Rappers and the etiquette of being online. We also play a game of ‘Guess The Real Rapper’ to further illustrate the fine line between URL and IRL.
Von Pea is a founding member of the group Tanya Morgan and a charter member of Okayplayer and he also moderated the message boards. so he has tons of experience dealing with people online.
To order 15 Year Anniversary pressing of Brooklynati visit: vinylmeplease.com
For more information visit:
Von Pea: Instagram.com/VonPea
Donwill: Donwill.substack.com
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris, Edited by Kobina Baffour & Tony Mui. Art Direction by Kaushik Kalidindi. Music Production by Von Pea.
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- 2024 Summer Round UpSep 5, 2024 · 21 minSummer 2024 is almost over so this week we went outside to find out what the streets were feeling. Top artists, album and of course song of the summer. We are still taking answers to all the questions so feel free to chime in on the comments as well!
For more information visit:
Donwill: Donwill.me
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris. Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- Lessons from Legends feat Rodney JerkinsAug 29, 2024 · 50 minThis week we talk to Rodney Jerkins about his time spent working with Micheal Jackson, Brandy, Mary J Blige, Whitney Houston and Beyonce, to name a few. We also get to the bottom of a few unsolved mysteries that have been rattling around my brain.
Rodney Jerkins is a Grammy award-winning producer and songwriter who has worked with more than his fair share of legends.
For more information visit:
MAVI: Mavi.bandcamp.com
Donwill: Donwill.substack.com
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sssay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris. Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- Artist Profile: MAVIAug 22, 2024 · 21 minThis week we talk to MAVI about his latest release, seeking the approval of your parents and the concept of a shadow self. He wasn’t able to make it into the studio so we did it via Zoom.
MAVI is a hip-hop artist from Charlotte North Carolina and his new album is titled shadowbox. He’s been widely praised for his mindful rhymes and evocative instrumentals.
For more information visit:
MAVI: Mavi.bandcamp.com
Donwill: Donwill.substack.com
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sssay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris. Edited by Travis Harris & Kobina Baffour. Art Direction by Kaushik Kalidindi. Graphic Design by Crystal Simone. Music Production by Von Pea.
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- New Artist Energy feat Lalah HathawayAug 15, 2024 · 48 minThis week we talked to Lalah Hathaway about how she stays inspired to keep her music fresh. We also talk about hip-hop samples, vocal colors, vocal signatures, and a whole bunch of other fun stuff.
Layla is a Grammy award-winning singer, artist, writer, and producer and she is also the daughter of Donny Hathaway. Her new album Vantablack is available everywhere now.
For more information visit:
Lalah Hathaway: lalahhathaway.com
Donwill: Donwill.substack.com
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris, Edited by Kobina Baffour. Art Direction by Kaushik Kalidindi. Music Production by Von Pea.
Learn more about your ad choices. Visit megaphone.fm/adchoices
- Artist Profile: JSWISSAug 8, 2024 · 36 minThis week we talk to JSWISS about his career and upcoming release. We also discussed a few recent events including the LOX on NPR’s Tiny Desk, who his personal Big 3 are and Nardwuar’s iconic journalism.
JSWISS is an artist with a career unlike any one as he’s worked with several jazz luminaries including Nicolas Peyton, Elvis Costello, Casey Benjamin, Keyon Harold and Marcus Machado. (album with Micheal Lionheart.
For more information visit:
JSWISS: jswissmusic.com
Donwill: Donwill.substack.com
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sessay for Okayplayer Media. This episode was written and hosted by Donwill. Produced by Travis Harris, Edited by Kobina Baffour. Art Direction by Kaushik Kalidindi. Music Production by Von Pea.
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- Canadian Hip Hop & DJ Battles feat A-TrakAug 1, 2024 · 36 minThe Almanac of Rap is back and for our Okayplayer-produced season opener and our first guest is A-Trak.
A-Trak is a Canadian DJ, record producer, and co-founder of Fool’s Gold Records. We discuss Canadian hip hop, the impact of Fool’s Gold and give him the chance to give the Grammy acceptance speech he never got to make.
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okayplayer Media. This episode was written and hosted by Donwill. Produced & Directed by Travis Harris. Edited by Kobina Baffour & Tony Mui. Art Direction by Kaushik Kalidindi. Music Production by Von Pea.
For more information about A-Trak visit: www.atrak.com (http://www.atrak.com)
For more information about Fool’s Gold Visit: www.foolsgoldrecs.com (http://www.foolsgoldrecs.com)
For more information about Donwill visit: www.donwill.me (http://www.donwill.me)
For more information about Okayplayer visit: www.okayplayer.com (http://www.okayplayer.com)
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- The Almanac of Rap Questions Live feat Josh Gondelman and Petey DeAbreauNov 21, 2023 · 1 hr 18 minTo read show notes for this episode go to donwill.substack.com
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- The Almanac of Rap Questions Live feat ItstherealNov 14, 2023 · 1 hr 41 minTo read the show notes for this episode go to donwill.substack.com
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- Gods and Gangs feat Timmhotep & DJ R-TisticNov 7, 2023 · 37 minToday's episode is a compilation of sorts. I asked Timmhotep and DJ R-Tistic (two past guests) two wild questions - which religion and which gang has had a bigger impact on hip hop.
We also talk about rappers that have turned to religion.
It's a fun one.
And oh yeah subscribe to the new newsletter over at donwill.substack.com
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- Comedy and Hip Hop Part 2 feat Diallo Riddle & LuxxuryOct 31, 2023 · 39 minIn this episode we discuss parody rap songs with none other than DIallo RIddle and Blake 'Luxxury' Robin. We also take a look at Russ Parr's history as a parody rap artist and track down The Rappin Duke to see what he's been up to.
You can check out One Song hosted by DIallo RIddle and Blake 'Luxxury' Robin here.
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
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- Comfort Albums: Almanac MiniOct 24, 2023 · 7 minDo you have a comfort album? If so leave your response in the comments section of this Instagram post and I'll include them in an upcoming episode!
I'll be back in your
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- Comedy and Hip Hop Part 1 feat Will MilesOct 10, 2023 · 37 minIn this episode we talkt to Will Miles about the distinct bond between rap and comedy. We look at a few comedians who have bars and talk about a few rappers that are actually hilarious
You can find out more about Will Miles at his website
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
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- Artist Profile: Armand Hammer in 2015Sep 26, 2023 · 30 minOn this episode we revisit an interview that I conducted in 2015 with Billy Woods and Elucid of the rap group Armand Hammer. They were fresh off of the release of their album Furtive Movements and preparing to release a set of solo albums. We talk about their origins as a rap group and their creative process.
Their new album We Buy Diabetic Test Strips drops on 9/29 via Fat Possum Records.
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
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- LA Rap and DJ Battles feat DJ R-TisticSep 19, 2023 · 30 minOn today's episode we talk to DJ R-Tistic about LA dance music, west coast rap and discuss a few fantasy DJ match-ups. DJ R-Tistic is an LA native who has DJ’ed events for everyone from Stevie Wonder to Issa Rae. You can find out more about him at his website.
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
Twitter.com/donwill
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The Almanac of Rap:
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- Pussy Rap and Misogynoir feat DJ TaraSep 12, 2023 · 21 minIn this episode I try to wrap my head around the co-relation between Pussy Rap and the conversation about rap being boring or uninspired or whatever and lean on my friend DJ Tara for support.
You can tune in to her radio shows and find out where in the world she's spinning next at her website.
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
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The Almanac of Rap:
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- Jersey Club and Tik Tok Dances feat MorufSep 5, 2023 · 25 minIn this episode Donwill talks to Moruf to figure out what exactly Jersey Club is. He also tries to figure out if Tik Tok dances are the new break dancing.
You can find out more information about Moruf and Some Jazz Playing here
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
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The Almanac of Rap:
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- What Happened to Hip House feat Dave Giles IIAug 29, 2023 · 26 minIn this episode Donwill talks to Dave Giles II to figure out what happened to the danceable hip-house style of rap music. He also brings up that time KRS-One battled KRS.
You can find out more information about Dave and his many dope projects here
For a list of 10 Chicago House & Hip House songs, Kool Rock Steady's music video, a short documentary on Hip House and more visit donwill.me/aor/hip-house
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Donwill:
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The Almanac of Rap:
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- Season Two Is Coming!Aug 11, 2023 · 5 minWe are coming back August 2023!
To check out past episodes, join my newsletter or get more information in general visit www.donwill.me/aor
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- Love & Hip Hop feat Kathy IandoliApr 25, 2023 · 35 minThe mix for this episode is available on Soundcloud.
Kathy is an author and professor at NYU who’s written books with Lil Kim, Prodigy and T Pain. You can learn more about her work here
Follow the us on social media:
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Donwill - Twitter / Instagram
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- Politics As Usual feat TimmhotepApr 18, 2023 · 36 minThe mix for this episode is available on Soundcloud.
Timm is a writer and curator.who created Levels & The One’s for pitchfork. He hosted Squeeze Radio on the legendary 89.9 FM with Sucio Smash and currently has his own show on NTS radio.
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
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- The Spelling Bee feat Petey DeAbreuApr 11, 2023 · 34 minThe mix for this episode is available on Soundcloud.
Petey is NYC comic who reps the Bronx thoroughly. He has credits on Comedy Central, That Damn Micheal Che and stages across the country. For more info check out his Instagram
Follow the us on social media:
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Donwill - Twitter / Instagram
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- Rap Groups feat Tajai & Von PeaApr 4, 2023 · 28 minThe mix for this episode is available on Soundcloud.
Tajai is a founding member of Souls of Mischief/Hieroglyphics. For more info check out their website. Von Pea is a founding member of Tanya Morgan. For more info check out their website
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- Industry Plants feat Psalm OneMar 28, 2023 · 27 minThe mix for this episode is available on Soundcloud.
Psalm One is a chemist turned rapper turned author (Her Word is Bond) and founding member of The Shift Cooperative, a Minneapolis based Mutual aid fund providing relief and support to disadvantaged and underserved communities. For more info check out her website
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- Rap Singers feat PhonteMar 21, 2023 · 29 minThe mix for this episode is available on Soundcloud.
Phonte is a rapper, singer and producer who is a member of Little Brother & Foreign Exchange. He also co-hosts Questlove Supreme and does the music for Sherman’s Showcase.
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Donwill - Twitter / Instagram
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- Rapsploitation Soundtracks feat Wyatt CenacMar 14, 2023 · 31 minThe mix for this episode is available on Soundcloud.
Wyatt Cenac is an Emmy award winning comedian, actor, writer & producer. For more information visit wyattcenac.com
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Donwill - Twitter / Instagram
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- Unhinged Content feat Jean GraeMar 7, 2023 · 28 minThis episode originally aired on March 7, 2023
The mix for this episode is available on Soundcloud.
Jean Grae is a writer, comedian and retired rapper. You can find out more about what she’s been up to at patreon.com/JeanGrae
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