Donwill’s ‘The Almanac of Rap’ Enters its Elite Era

Photo by Kaushik Kalidindi for Okayplayer.

How was the learning process like with some of your earlier recordings—was there a certain point or interview when you finally felt you hit your groove?

The learning curve has evolved over the years. In the first season, it was about assembling the episodes. Each one was the equivalent of writing, recording and editing a full album. Each episode also had its own specific difficulties.

In the second season, the learning curve was a lot of boring technical stuff like RSS feeds and podcast analytics. Things that aren’t so sexy but are the lifeblood of actually publishing in the digital landscape.

But for both seasons the biggest learning curve in general was about collaboration, learning how to work with people as opposed to doing everything by myself. I am fiercely independent which can make working with people kinda tough but OKP has proven to be a really amazing company to partner with.

The interview portion honestly came easy for me mostly because I’ve been doing it for a long time. I’ve been on both sides of the table as an interviewer or interviewee so I can tell when the interview is going good or bad. I can also figure out how to reroute the energy in the moment a lot of times. I feel like if you are curious, almost anything is interesting and I also believe that there are no boring people either.

What episodes/guests stand out to you as your favorites from the first 2 seasons?

It’s hard to pick favorite episodes because each one is special and has its own stand-out moments but here are two from each season that I’d consider essential listening:

“Politics as Usual w/ Timmhotep” — This episode is about some of rap’s more political moments. Not just Public Enemy but also the time Luther Campbell ran for mayor. Timmhotep is such a sharp and insightful guest and he gave so much wonderful context to the conversation.

“What Happened to Hip House with Dave Gilles II” — In this episode I openly pondered if hip-house was still a genre. Me and Dave talked about Chicago’s early hip-house scene and even got some clarity from Common himself about one of his bars.

“Pussy Rap w/ DJ Tara” — This episode was a fun one because as I recorded it I realized that I had to have a woman’s POV so her interview was actually a response to what I was working on. I had a lot of fun putting it together.

“Unhinged Content w/ Jean Grae” — We talk about the unhinged genius of LL Cool J and it leads us to some hilarious places. Anytime I team up with Jean the results are epic and this is no exception. This is the first episode of the series and I feel like it embodies everything that the show is about.

Pivoting to this new season with Okayplayer producing the podcast, how does this milestone feel? Does it feel like a 360-moment since you originally started off in this music/media space through the OKP boards?

It truly does. The OKP message boards are where I found my first audience. It was a community bound by common interests and I’m still friends with a lot of Okayplayers to this day.

I’d almost liken the message boards to a second college because I learned a lot about internet etiquette and being online. This was long before social media so I was pretty well acclimated when the social networks were introduced.

And with it being a message board the communication was solely via written word. No memes, no photos, no voice notes; just you and the words. It’s where I really practiced my online voice.

Also, now the podcast has a visual element as well. What surprises and new features can the audience expect with this new enhancement?

We are honestly still seeing how far we can push the visual elements. It’s an exciting time. There will of course be video elements and found footage but we’re also using graphic elements to really flesh it out.

We are also working out a livestream version of the show as well to make it feel even more interactive but that is still in development so the surprises will be surprising to me as well!

Let’s dig into your conversation/hosting style for a bit — how would you describe it and what do you feel sets The Almanac of Rap apart from all the other hip-hop content available for listeners?

My interview style is journalistic but lighthearted. Conversational in tone but pointed in intention. I try to keep shit whimsical but informative.

I think the thing that sets this show apart is how well-researched it is. It’s fact-based entertainment but still has a fun tone to it. I set out to make a show that wasn’t built around speculation or second-hand information and opinions. I am trying to find answers to questions that I have so I am talking to guests that have insight which gives each conversation so much intention.

My ultimate goal is to provide a level of context to the landscape. So much of the internet is about cropping out the context to get the hot take or being hyperbolic to get a rise out of people. AOR is about rabbit holes that music nerds fall down and the humorous things they find in them.

Are there any other hosts/shows in this space that inspire/motivate you/

I listen to a lot of podcasts and I tune in to each one for different things. Here are some of my favorite music-related ones:

What Had Happened Was with Open Mike Eagle, The Questions with Sean Kantrowitz, Diggin The Greats, Rob Markman’s new YouYube Show, Questlove Supreme, Juan Ep with Peter Rosenberg and Cipha Sounds, anything that ItsTheReal does and the Reflections of A DJ podcast. Speedy Morman is dope too.

And The Combat Jack Show is the greatest rap music podcast of all time. Period. He’s the podcasting North Star and I have to shout out Dallas Penn too. They are both giants in the world of hip-hop podcasting and a lot of what I do is in homage to them.

I really enjoy shows that have some kind of historical value. People who help archive the culture.

To close, can you share why everyone should be checking for this brand new season of Okayplayer Presents The Almanac of Rap?

It goes without saying that I’m biased, but the show is just excellent. It’s made by people who care immensely about the subject. It examines sides of stories that you might not have even thought to look at. It is also clinically proven to make you smarter and more interesting at dinner parties. Trust me. Why would I lie to you?