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!
Copyright: © Working Creative
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:
🤳🏾 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: 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:
🤳🏾 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 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!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
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:
🤳🏾 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 Durand Bernarr:
Instagram: @durandbernarr
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:
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!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
Website: Donwill.me
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!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
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!🎙️
Follow Donwill for fun hip-hop history, cultural commentary, and more.
Substack: New Music Tuesdays
Instagram/Threads: @donwill
Mixcloud: Donwill
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 Myles 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
Instagram/Threads: @donwill
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
Our TOPPODCAST Picks 
