Stay ConnectedThe Almanac of Rap is a two-time Webby Award-winning show that examines trends in hip hop and their impact over time…and it’s way more fun than that description makes it sound. Each week, our host 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.
If you’re new to the Almanac, start here!
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On this episode of The Almanac of Rap, Donwill sits down with visionary producer, filmmaker, label founder, and creative architect Flying Lotus for a wide-ranging conversation about music, film, creativity, and the art of world-building.
From pioneering the Los Angeles beat scene and launching Brainfeeder Records to directing boundary-pushing films and secretly becoming Captain Murphy, Flying Lotus has spent his career challenging expectations and creating entirely new lanes for artists to exist in.
FlyLo discusses his upcoming EP Big Mama, a meticulously crafted project built without loops and designed to feel alive, constantly evolving, and impossible to predict. He also reflects on growing up surrounded by musical greatness through the legacy of Alice Coltrane, how family shaped his understanding of creativity, and why seeing artistic success firsthand made it easier to imagine his own future.Flying Lotus breaks down:
The origins of Brainfeeder Records and working with artists like Thundercat, Kamasi Washington, and Louis Cole
Growing up in the legacy of Alice Coltrane and Marilyn McLeod
The challenges of filmmaking versus music production, and directing Kuso and Ash
Producing music with computers during an era dominated by hardware
🤳🏾 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 Flying Lotus
Instagram: flyinglotus
Music: Flying Lotus - BIG MAMA
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
For the first-ever live taping of The Almanac of Rap in New York City, Donwill welcomes archivist, researcher, and Mixtape Museum founder Regan Sommer McCoy for a deep dive into the history, culture, and future of mixtapes. Recorded live at Ludlow House in partnership with On Air Presents, this special episode explores how cassette tapes transformed music sharing, why mixtapes became hip-hop's original social media platform, and what we lose when we reduce playlists to algorithms and streaming metrics.
Sommer shares the origin story behind the Mixtape Museum, a community-driven archival project dedicated to preserving mixtape culture, cassette history, and the stories behind the music. Sommer breaks down:
The evolution of the mixtape; from homemade radio recordings and DJ exclusives to street albums, playlist culture, and modern-day archives.
Legendary mixtape figures including DJ Clue, Ron G, DJ Screw, Kid Capri, DJ Drama, Don Cannon, Justo Faison and the Mixtape Awards
Preservation, ownership, curation, and the importance of documenting hip-hop history before it disappears.
The future of mixtapes in a streaming and AI-driven world
🤳🏾 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 Regan Sommer McCoy
Instagram: dearsommer
Web: Sommer.nyc
Web: Mixtape Museum
Instagram: mixtapemuseum
Soundcloud: The Mixtape Museum
Follow On Air Presents
Instagram: onairpresents
Web: Onairpresents.com
Event Recap: Photos
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.
Note: This episode was pre-recorded on March 24, 2026.
Learn more about your ad choices. Visit megaphone.fm/adchoices
This 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
This 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
This 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
Before 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
What 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
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
On 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
In 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
In 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
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