The Almanac of Rap

Maiya the Don spent three years figuring out what she actually wanted to say. After Hot Commodity introduced a Brooklyn rapper capable of moving between drill, pop and straight-up bars, touring with Flo Milli and building an audience that first knew her as a beauty creator, Maiya found herself confronting a harder question: what does her music sound like when she's no longer trying to prove she can do everything? On this episode of The Almanac of Rap, she talks to Donwill about creating The Fine Print Club, her book club built around reading, community and creating space for Black women; recommends everything from S.A. Cosby to DMX; and hilariously puts her literary knowledge to the test against some of urban fiction's wildest book titles. 

Between books and bars, she also makes a case for independence, explains why artists shouldn't run from being content creators and delivers a warning to anyone tempted to underestimate her pen: Precious Cargo (her new album) may be personal, but Maiya the Don still came to rap.  Maiya the Don breaks down:

• Why Precious Cargo became the coming-of-age album she needed three years to make

• Turning a beauty-content following into the foundation for a rap career

• Why independence gives her control over both her artistry and narrative

• Building The Fine Print Club and creating literary community for Black women

• Why “TSA” is her answer to anyone questioning a woman rapper's pen

🤳🏾 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: Maiya The Don 

Instagram: @maiyathedonn    

Album: Precious Cargo  ⁠ 

Book Club: @fineprint.collective

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 Leron Thomas became the left-field rapper Pan Amsterdam, he was a Houston jazz prodigy sharing classrooms with Robert Glasper, touring with Bilal and building a reputation as a trumpeter willing to wander far outside jazz's borders. In this episode of The Almanac of Rap, Thomas traces that journey from Houston's High School for the Performing and Visual Arts to New York's jazz scene, and explains how listening to everyone from the Geto Boys and Busta Rhymes to David Bowie and Frank Zappa eventually made genre feel less like an identity than a suggestion. Leron Thomas breaks down:

• How touring with Tanya Morgan helped inspire his Pan Amsterdam alter ego

• Going from Robert Glasper's Houston classmate to Bilal's touring band

• How Iggy Pop discovered Pan Amsterdam and turned the connection into Free

• Why Busta Rhymes, Geto Boys and Southern rap influenced his jazz phrasing

• The creative tug-of-war between Leron Thomas, Pan Amsterdam and genre itself

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Substack: New Music Tuesdays

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Mixcloud: Donwill

Website: Donwill.me

Follow: Leron Thomas 

Instagram:  @leronthomas98

Spotify:  Leron Thomas

Apple Music: ⁠ Pan Amsterdam

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 episode of The Almanac of Rap, Donwill heads south to explore the past, present and future of New Orleans hip-hop with rising rapper, producer and 2026 XXL Freshman La Reezy.

La Reezy shares how filming run-and-gun videos around his hometown helped him build an audience outside Louisiana, how a viral streetcar performance caught PJ Morton’s attention, and why he considers himself a “leader of the youth” within a new generation of New Orleans artists. For La Reezy, representing the city isn’t simply an aesthetic, it’s central to his strategy, community and identity.

Fresh off recognition from the National Hip-Hop Museum and an appearance in Kendrick Lamar’s Super Bowl experience, La Reezy also opens up about faith, family, learning from Jon Batiste, studying Kendrick from behind the scenes and his ambitions beyond music. La Reezy breaks down:

• Why representing your hometown can be a competitive advantage
• The streetcar video that caught PJ Morton’s attention
• Performing at Keith Lee’s Family Day
• The ideas behind his debut album, Skiddle Bandana
• His dream of producing for Lil Wayne and NBA YoungBoy  

Check out archived episodes of The Almanac of Rap at: https://almanacofrap.com/  📚

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Follow: La Reezy

Instagram: lareezymusic

Album: Skiddle Bandana

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 episode of The Almanac of Rap, Donwill sits down with multi-platinum, Grammy Award-winning artist Everlast for a wide-ranging conversation about reinvention, longevity and a career that has consistently refused to stay inside one genre.

Everlast reflects on returning to music with Embers to Ashes after nearly eight years, an album shaped by the pandemic, divorce, losing his home in the Woolsey Fire and eventually finding his way back to songwriting. He takes Don through his early days with Ice-T’s Rhyme Syndicate and Divine Styler, the friendships that connected him with DJ Muggs, B-Real and Cypress Hill, and the unlikely series of events that led to House of Pain and the creation of “Jump Around.”

The conversation also revisits the genre-smashing Judgment Night soundtrack, the transformation that produced Whitey Ford Sings the Blues and “What It’s Like,” his relationship with Yelawolf, and why his decades-old beef with Eminem is firmly in the past. Everlast also considers what it takes to create a genuine anthem in today’s algorithm-driven music industry and gives flowers to the artists who helped make his career possible. Everlast breaks down:

• Returning with Embers to Ashes after an eight-year album hiatusLosing his home in the Woolsey Fire and rebuilding his life
• How COVID and fatherhood changed his relationship with touring
• House of Pain's unexpected relationship with Ireland
• Everlast says his Eminem beef is long over.

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Follow Everlast

Instagram:  ogeverlast  

Facebook: Everlast

Spotify: Everlast 

Apple Music: Everlast

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 throwback episode of The Almanac of Rap, Donwill sits down with Grammy Award-winning songwriter and Chicago native Dave Giles II for a deep dive into Hip House, Chicago house music and the city's evolving relationship with hip-hop.

Dave, co-writer and producer of Beyonce’s hit song “Cozy” from her #1 album Renaissance, remembers growing up in a Chicago where house music wasn't a separate scene; it was simply part of everyday Black life, from radio and skating rinks to block parties and neighborhood venues. He and Donwill revisit pioneers like Mike Dunn, Chicago's Black club culture, and the unique style of rapping that developed alongside house music. Dave breaks down:

• The connection between the geography of Chicago's house era to the neighborhoods that later became central to drill music
• Examines how housing displacement, demolished public housing communities and neighborhood upheaval reshaped the city's culture
• Common's memories of Chicago nightlife
• Hip House's connection to hip-hop's Jamaican party-rocking roots
• Dave's Grammy win and work on Beyoncé's Renaissance

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Mixcloud: Donwill

Website: Donwill.me

Follow: Dave Giles II

Instagram:  davegilesii   

Web: www.davegilesii.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

On this episode of The Almanac of Rap, Donwill sits down with hip-hop pioneers The Jungle Brothers to revisit the friendships, records and unlikely moments that helped shape one of rap's most influential eras.

The Jungle Brothers take Don back to their teenage years, from high school talent shows and homemade cassette recordings to basement studios, legendary New York clubs and their earliest encounters with DJ Red Alert, Q-Tip, De La Soul and the artists who would become the Native Tongues collective. They also unpack the story behind “I’ll House You,” their groundbreaking collision of hip-hop and house music, and explain why genre boundaries simply didn't matter to their generation.  The Jungle Brothers breakdown:

• Meeting as teenagers, touring Europe and the communal studio culture of early hip-hop
• Why Red Alert deserves greater recognition in hip-hop history
• De La Soul, Buddy and Calliope Studios
• How “I'll House You” emerged before rap and house became rigid categories.

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Mixcloud: Donwill

Website: Donwill.me

Follow The Jungle Brothers

Instagram:  @junglebrothers4life

Spotify: Jungle Brothers  

Apple Music: Jungle Brothers

Link.tree:  @junglebrothers

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 episode of The Almanac of Rap, Donwill sits down with GRAMMY-nominated rapper, singer, and actor CHIKA for one of the funniest and most wide-ranging conversations of the season. From going viral on Instagram and signing with Warner Records to launching her career during the COVID-19 pandemic, CHIKA reflects on the unexpected highs and difficult realities of becoming one of hip-hop's most celebrated new voices.  Along the way, Don and CHIKA spend several minutes passionately debating fountain pens, celebrate Montgomery's official CHIKA Day, and revisit the legendary Montgomery Riverfront Brawl.  CHIKA breaks down:

CHIKA's viral rise from Instagram freestylesNavigating online controversy, mental health and social mediaThe Montgomery Riverboat Brawl ("Fade in the Water") aka CHIKA DaySurviving the isolation of pandemic success Why artists should never let social media define themThe making of Sampson

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Follow CHIKA

Instagram:  chikalogy   

Spotify:  CHIKA

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 episode of The Almanac of Rap, Donwill sits down with Grammy Award-winning singer, songwriter, producer, and internet icon Durand Bernarr for a conversation that blends music history, creative identity, and plenty of laughs. From growing up in a household filled with instruments, vocal coaching, and Earth, Wind & Fire tour buses to becoming one of R&B's most distinctive voices, Durand reflects on the experiences that shaped both the artist and the personality fans know today.

The pair discuss Durand's latest album Bernarr, how winning his first Grammy accelerated his career, and why social media has become an extension of his artistry rather than just a promotional tool. They also dive into his deep love for YouTube-era music discovery, the lasting influence of artists like J*DaVeY, Crash Cut, Vula, and Rochelle Jordan, and why authenticity will always outlast chasing trends. Durand breaks down:

Queer visibility in music

Working alongside Earth, Wind & Fire

His love of DJing and production 

His unforgettable Grammy acceptance speech, and the importance of embracing every version of yourself. 

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Substack: New Music Tuesdays

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Mixcloud: Donwill

Website: Donwill.me

Follow Durand Bernarr:

Instagram:  @durandbernarr  

Web: www.durandbernarr.com/

Album: BERNARR.

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 throwback episode of The Almanac of Rap, Donwill revisits his conversation with DJ R-Tisitc, one of Los Angeles' most respected DJs and music curators. From his early days producing for The Game's Black Wall Street to becoming a sought-after DJ for artists including Stevie Wonder and Issa Rae, DJ R-Tisitc reflects on his unconventional path into DJing and how studying regional music scenes helped shape his career. DJ R-Tisitc breaks down:

The unique musical identity of Los Angeles; from G-Funk and electro to jerkin' to crumping and the influences of hyphy music.

Why drill music has never truly found a home in Southern California. 

How producers like DJ Mustard, Terrace Martin, Channel Tres, and Blxst represent different chapters in the evolution of the city's sound.

Follow Donwill for fun hip-hop history, cultural commentary, and more.

Substack: New Music Tuesdays

Instagram/Threads: @donwill

Mixcloud: Donwill

Website: Donwill.me

Follow DJ R-Tisitc:

Instagram:  @djrtistic

Web: https://www.djr-tistic.com/ 

Twitch: rtistic310 

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 special episode of The Almanac of Rap, Donwill heads to Los Angeles for the BET Media House Experience, gathering an all-star lineup of artists, creators, executives, and media personalities to ask ONE question: What does winning an award actually mean?

From rising stars visualizing their first BET Award to veterans reflecting on careers filled with accolades, this special episode captures honest conversations about ambition, validation, legacy, and the relationship between recognition and impact. Guests including Rapsody, Slim Jxmmi, Salt, Kenny Burns, Miles Minnick, Hurricane Wisdom, Big Cat, Deontay Kyle, The War and Treaty, and more share what they'd say if they stepped onto the BET stage and whether awards are the goal or simply the byproduct of meaningful work.

Along the way, Don explores the idea that while trophies may celebrate achievement, an artist's greatest accomplishment is often the community they've built and the culture they've influenced. It's a candid snapshot of Black creativity during one of music's biggest weekends and a reminder that success means something different to everyone.

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Follow our Guest from the BET Media House Experience:  

Rapsody, Slim Jxmmi, Salt, Kenny Burns, Miles Minnick, Hurricane Wisdom, The War and Treaty, Deontay Kyle, Big Cat, Nico Brim, Beno Rideaux, Shane, Beverly Face, Von Wyc, Stockton Vice Mayor Jason Lee

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 special episode of The Almanac of Rap, Donwill opens the vault and shares some of the best conversations that didn't make the final edits of the first half of Season 4. From forgotten stories and extended interviews to behind-the-scenes insights, these bonus moments offer a deeper look at the people and ideas that continue to shape hip-hop culture.

Hear Masta Ace reflect on New York City's legendary car culture, the art of "jeep beats," and writing songs during Will Smith's Millennium sessions. Michael Holman revisits the legacy of Graffiti Rock, the evolution of breaking from the streets to the Olympics, and why Fab Five Freddy remains one of hip-hop's most influential ambassadors. Finally, producer Jake One unpacks the rise of lo-fi beats, the importance of making timeless songs over viral content, and the unexpected origins of his modern funk project, Tuxedo.  Bits & Pieces Vol 1 breaks down:

Masta Ace on New York's '90s car culture and the science behind classic "jeep beats"

Michael Holman on Graffiti Rock and why breaking belongs in the Olympics

Fab Five Freddy's impact on hip-hop culture

Jake One on lo-fi beats and beat culture

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Substack: New Music Tuesdays

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Mixcloud: Donwill

Website: Donwill.me

Follow Michael Holman:

Instagram:  @michaelholman101

Follow Jake One:

Instagram: jakeuno

Web: snarejordan.com

Bandcamp: Jake One

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

This week on a special minisode of The Almanac of Rap, Donwill is joined by Okayplayer's Audio Marketing Strategist and longtime collaborator Faybeo’n “LiKWUiD” Mickens for a behind-the-scenes conversation about the making of the recent Shaggy episode.

Together, they unpack Shaggy's stories about military cadence, reggae's influence on hip-hop, and the origins of his unmistakable vocal style before taking a detour into Eddie Murphy's surprisingly massive influence on rap culture. From Eddie Murphy Raw to Coming to America, the conversation explores how comedy, music, and hip-hop have always been more connected than they seem.

Don and Fay close out with a fun debate inspired by the “semiquincentennial” weekend events during the Fourth of July: What is the most American moment in hip-hop history? 

Call 1-877-DONWILL (366-9455) and tell Don your pick. It could be a song, an album, a performance, a headline, or a completely ridiculous moment…the more whimsical, the better. 

Follow Donwill for fun hip-hop history, cultural commentary, and more.

Substack: New Music Tuesdays

Instagram/Threads: @donwill

Mixcloud: Donwill

Website: Donwill.me

Follow Faybeo’n Mickens

Instagram:  @likwuid

Web: FaybeonMickens.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

On this episode of The Almanac of Rap, Donwill sits down with Grammy Award-winning artist Shaggy for a wide-ranging conversation about building one of the most enduring careers in music, navigating the intersection of reggae and hip-hop.

From his early days recording "Oh Carolina" while serving in the U.S. Marines, to the global success of "Boombastic," "Angel," and "It Wasn't Me," Shaggy reflects on the moments that shaped his career and the mindset that helped him remain relevant for more than three decades. Shaggy breaks down:

Working with Michael Jackson, Sting, Spice, and Eddie Murphy

Dancehall's influence on hip-hop, and Jamaica's rich lyrical tradition

His new album Lottery, and starring in The Last Ship at New York's Metropolitan Opera.

🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️

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Website: Donwill.me

Follow Shaggy

Instagram: direalshaggy

Tik Tok: DiRealShaggy Facebook: Shaggy 

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 episode of The Almanac of Rap, Donwill sits down with Awon, and Joe Miles of The Other Guys for a conversation about independent hip-hop, running record labels, vinyl culture, and the realities of building sustainable careers outside the major label system.

Awon is the founder of Don't Sleep Records, while Joe Miles runs HipNott Records, home to artists including Skyzoo, Tanya Morgan, and Shay Noir. Together, they discuss their new collaborative project Solidified, the years-long friendship that led to the album, and what it takes to balance artistry with entrepreneurship.  Awon and Joe break down:

The challenges of operating independent labels in today's music landscape  from pressing vinyl and managing distribution to navigating shipping costs, manufacturing delays, and maintaining direct relationships with fans. 

Lessons learned from years of self-releasing music, retaining ownership of their catalogs, and building businesses rooted in community rather than competition.

Mentorship, family life, touring, jazz influences in hip-hop, and why ownership remains one of the most important principles for artists seeking longevity.

🤳🏾 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

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Mixcloud: Donwill

Website: Donwill.me

Follow: The Other Guys

Instagram:  @otherguysmusic   

Website:  HipNott Records  

Follow:  Awon

Instagram:  @awon1988

Website: Dontsleeprecords.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

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

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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   

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

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

Grammy-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

In 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

🤳🏾 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:

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

🤳🏾 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

Religion 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

This 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

📢 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

In 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

What 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

What 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.

Substack: New Music Tuesdays

Instagram/Threads: @donwill

Mixcloud: Donwill

Website: Donwill.me

Follow Cupid: 

Instagram: @officialnewcupid

TikTok: @officialnewcupid

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

For 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.

Learn more about your ad choices. Visit megaphone.fm/adchoices

This 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.

Learn more about your ad choices. Visit megaphone.fm/adchoices

This 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.

Learn more about your ad choices. Visit megaphone.fm/adchoices

This 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.

Learn more about your ad choices. Visit megaphone.fm/adchoices

This 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.

Learn more about your ad choices. Visit megaphone.fm/adchoices

This 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.

Learn more about your ad choices. Visit megaphone.fm/adchoices