The Almanac of Rap
The Almanac of Rap is a two-time Webby Award-winning show that examines trends in hip hop and their impact over time. Each week, host Donwill asks a question, presents a theory, and finds a guest to come to some sort of consensus about it. It's a show about rap, by a rapper who loves rap music.
Episodes
AOR Throwback: Hip House ft Dave Gilles II
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
Native Tongues feat The Jungle Brothers
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 enc
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 c
The Lean feat Durand Bernarr
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 refl
AOR Throwback: DJ R-Tisitc
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
The BET Awards 2026 feat Rapsody, Slim Jxmmi, Miles Minnick, Salt and more.
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 capture
Bits & Pieces Vol 1 feat Masta Ace, Michael Holman and Jake One
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'
AOR Mini: The Most "American" Moment in Hip Hop
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 befo
The Lottery feat Shaggy
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 reflect
Indie Labels ft Awon and The Other Guys
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
LA Beat Scene and Beyond feat Flying Lotus
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 Lot
Mixtape Museum feat Regan Sommer McCoy
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 or
Rapping Actors feat Jharrel Jerome
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 pictu
Rock n Rap feat Sequoia Holmes
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 e
The Rapper’s Rapper feat Grafh
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
Graffiti Rock feat Michael Holman
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 audien
The Chef feat Raekwon
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,
AOR Mini - Michael, Tara Chase and StaHHR
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 c
Big Ohio Status feat Blueprint
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
AOR Mini: Mailbag
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 compl
The Dungeon Family Tree feat Mr. DJ
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 so
AOR Mini: Underrated LPs
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 mes
The Falling Season feat Masta Ace
🤳🏾 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
Infamous to Infinite feat Havoc
🤳🏾 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
The Buddha and The Beat feat Born I
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 referenc
Rap Snacks feat Bun B
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 S
Canadian Connections feat Shad
📢 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 Ho
The Two First Namers Club feat Reuben Vincent & 9th Wonder
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 Reube
Type Beats feat Jake One
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
Black Line Dance Power Rankings feat Cupid
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
Art Official Intelligence feat Lupe Fiasco
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
Artist Profile: Homeboy Sandman
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
T
Artist Profile: Cory Gunz
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
Hip Hop Cartoons & Pioneer Power feat MC Lyte
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: Donw
Artist Profile: Cavalier
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 Do
Internet Rappers feat. Von Pea
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
2024 Summer Round Up
Summer 2024 is almost over so this week we went outside to find out what the streets were feeling. Top artists, album and of course song of the summer. We are still taking answers to all the questions so feel free to chime in on the comments as well!
For more information visit:
Donwill: Donwill.me
Okayplayer: Okayplayer.com
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Oka
Lessons from Legends feat Rodney Jerkins
This week we talk to Rodney Jerkins about his time spent working with Micheal Jackson, Brandy, Mary J Blige, Whitney Houston and Beyonce, to name a few. We also get to the bottom of a few unsolved mysteries that have been rattling around my brain.
Rodney Jerkins is a Grammy award-winning producer and songwriter who has worked with more than his fair share of legends.
For more information visit:
Artist Profile: MAVI
This week we talk to MAVI about his latest release, seeking the approval of your parents and the concept of a shadow self. He wasn’t able to make it into the studio so we did it via Zoom.
MAVI is a hip-hop artist from Charlotte North Carolina and his new album is titled shadowbox. He’s been widely praised for his mindful rhymes and evocative instrumentals.
For more information visit:
MAVI: Mavi
New Artist Energy feat Lalah Hathaway
This week we talked to Lalah Hathaway about how she stays inspired to keep her music fresh. We also talk about hip-hop samples, vocal colors, vocal signatures, and a whole bunch of other fun stuff.
Layla is a Grammy award-winning singer, artist, writer, and producer and she is also the daughter of Donny Hathaway. Her new album Vantablack is available everywhere now.
For more information visit:
Artist Profile: JSWISS
This week we talk to JSWISS about his career and upcoming release. We also discussed a few recent events including the LOX on NPR’s Tiny Desk, who his personal Big 3 are and Nardwuar’s iconic journalism.
JSWISS is an artist with a career unlike any one as he’s worked with several jazz luminaries including Nicolas Peyton, Elvis Costello, Casey Benjamin, Keyon Harold and Marcus Machado. (album with
Canadian Hip Hop & DJ Battles feat A-Trak
The Almanac of Rap is back and for our Okayplayer-produced season opener and our first guest is A-Trak.
A-Trak is a Canadian DJ, record producer, and co-founder of Fool’s Gold Records. We discuss Canadian hip hop, the impact of Fool’s Gold and give him the chance to give the Grammy acceptance speech he never got to make.
The Almanac of Rap is Executive produced by Donwill & Isha Sesay for Okaypl
The Almanac of Rap Questions Live feat Josh Gondelman and Petey DeAbreau
To read show notes for this episode go to donwill.substack.com
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The Almanac of Rap Questions Live feat Itsthereal
To read the show notes for this episode go to donwill.substack.com
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Gods and Gangs feat Timmhotep & DJ R-Tistic
Today's episode is a compilation of sorts. I asked Timmhotep and DJ R-Tistic (two past guests) two wild questions - which religion and which gang has had a bigger impact on hip hop.
We also talk about rappers that have turned to religion.
It's a fun one.
And oh yeah subscribe to the new newsletter over at donwill.substack.com
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Comedy and Hip Hop Part 2 feat Diallo Riddle & Luxxury
In this episode we discuss parody rap songs with none other than DIallo RIddle and Blake 'Luxxury' Robin. We also take a look at Russ Parr's history as a parody rap artist and track down The Rappin Duke to see what he's been up to.
You can check out One Song hosted by DIallo RIddle and Blake 'Luxxury' Robin here.
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Do
Comfort Albums: Almanac Mini
Do you have a comfort album? If so leave your response in the comments section of this Instagram post and I'll include them in an upcoming episode!
I'll be back in your
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Comedy and Hip Hop Part 1 feat Will Miles
In this episode we talkt to Will Miles about the distinct bond between rap and comedy. We look at a few comedians who have bars and talk about a few rappers that are actually hilarious
You can find out more about Will Miles at his website
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
Twitter.com/donwill
Instagram.com/donwill
The Almanac of Rap:
Instagram
Artist Profile: Armand Hammer in 2015
On this episode we revisit an interview that I conducted in 2015 with Billy Woods and Elucid of the rap group Armand Hammer. They were fresh off of the release of their album Furtive Movements and preparing to release a set of solo albums. We talk about their origins as a rap group and their creative process.
Their new album We Buy Diabetic Test Strips drops on 9/29 via Fat Possum Records.
Visit
LA Rap and DJ Battles feat DJ R-Tistic
On today's episode we talk to DJ R-Tistic about LA dance music, west coast rap and discuss a few fantasy DJ match-ups. DJ R-Tistic is an LA native who has DJ’ed events for everyone from Stevie Wonder to Issa Rae. You can find out more about him at his website.
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
Twitter.com/donwill
Instagram.com/donwill
The Alm
Pussy Rap and Misogynoir feat DJ Tara
In this episode I try to wrap my head around the co-relation between Pussy Rap and the conversation about rap being boring or uninspired or whatever and lean on my friend DJ Tara for support.
You can tune in to her radio shows and find out where in the world she's spinning next at her website.
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
Twitter.com/don
Jersey Club and Tik Tok Dances feat Moruf
In this episode Donwill talks to Moruf to figure out what exactly Jersey Club is. He also tries to figure out if Tik Tok dances are the new break dancing.
You can find out more information about Moruf and Some Jazz Playing here
Visit donwill.me/aor to check out the show notes and sign up for our newsletter!
Donwill:
Twitter.com/donwill
Instagram.com/donwill
The Almanac of Rap:
Instagram.com/theal
What Happened to Hip House feat Dave Giles II
In this episode Donwill talks to Dave Giles II to figure out what happened to the danceable hip-house style of rap music. He also brings up that time KRS-One battled KRS.
You can find out more information about Dave and his many dope projects here
For a list of 10 Chicago House & Hip House songs, Kool Rock Steady's music video, a short documentary on Hip House and more visit donwill.me/aor/hip-ho
Season Two Is Coming!
We are coming back August 2023!
To check out past episodes, join my newsletter or get more information in general visit www.donwill.me/aor
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Love & Hip Hop feat Kathy Iandoli
The mix for this episode is available on Soundcloud.
Kathy is an author and professor at NYU who’s written books with Lil Kim, Prodigy and T Pain. You can learn more about her work here
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
Visit Donwill.me to subscribe to my mailing list, book me for stuff or just find out more information in general.
Le
Politics As Usual feat Timmhotep
The mix for this episode is available on Soundcloud.
Timm is a writer and curator.who created Levels & The One’s for pitchfork. He hosted Squeeze Radio on the legendary 89.9 FM with Sucio Smash and currently has his own show on NTS radio.
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
Visit Donwill.me to subscribe to my mailing list, book me for s
The Spelling Bee feat Petey DeAbreu
The mix for this episode is available on Soundcloud.
Petey is NYC comic who reps the Bronx thoroughly. He has credits on Comedy Central, That Damn Micheal Che and stages across the country. For more info check out his Instagram
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
Visit Donwill.me to subscribe to my mailing list, book me for stuff or jus
Rap Groups feat Tajai & Von Pea
The mix for this episode is available on Soundcloud.
Tajai is a founding member of Souls of Mischief/Hieroglyphics. For more info check out their website. Von Pea is a founding member of Tanya Morgan. For more info check out their website
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
Visit Donwill.me to subscribe to my mailing list, book me for s
Industry Plants feat Psalm One
The mix for this episode is available on Soundcloud.
Psalm One is a chemist turned rapper turned author (Her Word is Bond) and founding member of The Shift Cooperative, a Minneapolis based Mutual aid fund providing relief and support to disadvantaged and underserved communities. For more info check out her website
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter
Rap Singers feat Phonte
The mix for this episode is available on Soundcloud.
Phonte is a rapper, singer and producer who is a member of Little Brother & Foreign Exchange. He also co-hosts Questlove Supreme and does the music for Sherman’s Showcase.
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
Visit Donwill.me to subscribe to my mailing list, book me for stuff or just f
Rapsploitation Soundtracks feat Wyatt Cenac
The mix for this episode is available on Soundcloud.
Wyatt Cenac is an Emmy award winning comedian, actor, writer & producer. For more information visit wyattcenac.com
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
Visit Donwill.me to subscribe to my mailing list, book me for stuff or just find out more information in general.
Learn more about you
Unhinged Content feat Jean Grae
This episode originally aired on March 7, 2023
The mix for this episode is available on Soundcloud.
Jean Grae is a writer, comedian and retired rapper. You can find out more about what she’s been up to at patreon.com/JeanGrae
Follow the us on social media:
The Almanac of Rap - Instagram
Donwill - Twitter / Instagram
Visit Donwill.me to subscribe to my mailing list, book me for stuff or just find
The Almanac of Rap Season 1 Trailer
Simply put, this is a trailer for ashow about rap made by a rapper.
There will also be mixes to accompany each episode and they can be found at Soundcloud.com/donwill once the episodes go live
Follow The Almanac of Rap
IG: Instagram.com/thealmanacofrap
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