The Almanac of Rap

Donwill/Okayplayer

The 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. Follow Donwill's Substack: https://workingcreatively.substack.com/

  1. 18h ago

    Genre-bending trumpeter Leron Thomas on Iggy Pop, Cool Keith, and Bilal

    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!🎙️ Follow Donwill for fun hip-hop history, cultural commentary, and more. Substack: New Music Tuesdays Instagram/Threads: @donwill 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

  2. Sep 3

    La Reezy on New Orleans Hip Hop, Skiddle Bandana & Becoming Rap’s Next Generation

    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!🎙️ Follow Donwill for fun hip-hop history, cultural commentary, and more. Substack: New Music Tuesdays Instagram/Threads: @donwill Mixcloud: Donwill Website: Donwill.me 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

  3. Aug 27

    Everlast on “Jump Around,” House of Pain, Eminem & Starting Over

    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!🎙️ Follow Donwill for fun hip-hop history, cultural commentary, and more. Substack: New Music Tuesdays Instagram/Threads: @donwill Mixcloud: Donwill Website: Donwill.me 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

    Everlast on “Jump Around,” House of Pain, Eminem & Starting Over
  4. Aug 20

    Dave Giles II on Hip House, Beyonce’s "Cozy", Chicago & the Roots of Drill

    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!🎙️ 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

  5. Aug 14

    The Jungle Brothers Tell the Origin Story of Native Tongues

    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!🎙️ 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

    The Jungle Brothers Tell the Origin Story of Native Tongues
  6. Aug 6

    Chika Day feat CHIKA

    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

    Chika Day feat CHIKA
  7. Jul 30

    Durand Bernarr: Grammy Wins, YouTube Origins & Finding Your Voice

    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!🎙️ 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   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

    Durand Bernarr: Grammy Wins, YouTube Origins & Finding Your Voice
4.8
out of 5
30 Ratings

About

The 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. Follow Donwill's Substack: https://workingcreatively.substack.com/