Meet Donwill, the Indie Hip-Hop Star Cultivating His Own Space in Comedy

Hip-hop indie star-turned-MC comedic DJ, Donwill, has become a sought-after figure in comedy. One half of the critically acclaimed hip-hop group Tanya Morgan, Donwill made a name for himself in comedy as Wyatt Cenac’s DJ for the widely popular weekly standup show Night Train featured on Seeso and as creator of the “Make Trump Drumpf Again” campaign song for Last Week Tonight with John Oliver.

In addition to Cenac and Oliver, Donwill has worked with a few of your favorite comedians and musicians such as Sasheer Zamata, Jessica Williams, Phoebe Robinson, and Jean Grae. His career trajectory is nothing but inspiring. Following the footsteps of other DJs in comedy such as Kid Capri (Def Comedy Jam), Cipha Sounds (Chappelle’s Show, Michael Che), and Tony Trimm (Hannibal Buress), Donwill went from MCing indie shows in 2003 to pissing off the President of the United States with a parody campaign song in 2016.

At the helm of dropping a new album with Tanya Morgan and a new season of Night Train, I spoke with Donwill about his relationship with comedy and hip-hop, his dream gig, and what exactly is an MC comedic DJ.

Tell me about yourself in two sentences.

My name is Donwill and I’m in a rap group named Tanya Morgan but I do a lot more than just rap. I also produce music, DJ parties/shows and trade riffs on stage with some of your favorite comedians.

How did you get involved in comedy?

My formal entrance into comedy came with the creation of Shouting at the Screen, an event that I do with Wyatt Cenac where we screen blaxploitation films, crack jokes, and play drinking games. I’ve riffed a bit between songs at a Tanya Morgan show but Shouting at the Screen was my first time performing in a true comedy space.

What made you want to get into comedy?

Rap is my first language, but growing up I also heavily related to shows like Robert Townsend’s Partners in Crime, In Living Color or movies like Hollywood Shuffle and I’m Gonna Git You Sucka. I can still do Tommy Davidson’s bit about singers ordering from McDonald’s verbatim in the same way I can deliver Nas’ Illmatic word for word. Maybe it was the fact that rappers and comedians both use words to entertain, but I’ve always saw a through line between music and comedy.

I’m in a rap group named Tanya Morgan and based on name alone you can expect there to be humor in my music. The humor we put into our debut album was less Lonely Island and more 3 Feet High and Rising, so no one considers us to be a parody group or anything like that, but they do know that we have a good sense of humor and a sharp musical wit.

You refer to yourself as an “MC comedic DJ.” What is that exactly?

MC Comedic DJ is basically a Venn diagram of my career. There are people that know me as an MC from my group Tanya Morgan, people that know me as a DJ, and people that know me as a guy who does comedy stuff. I don’t necessarily do standup, but I definitely do comedic things that are close enough to standup for me to be called a comedian on occasion. That descriptor is just something I threw in my Twitter bio, but I feel like it kinda perfectly encapsulates who I am at the moment.

Is it difficult straddling between hip-hop and comedy?

Not really. I bring all of myself to whatever it is I’m doing and it just so happens that in both worlds I get to be exactly who I am. They both use the same set of muscles, just in different ways. I have good taste in music and a really natural rapport with comedians and the crowd, so it all just kinda works.

The only real difficulty is finding a sensible way to marry the two, but for the most part my involvement in both has made me a stronger performer in general and exposed me to a lot of different audiences. I’m just trying to find a way to connect the dots between all of the things I do, because chances are if you enjoy one of the things you will enjoy the others.

Could you provide a brief historical context on the relationship between comedy and hip-hop?

The biggest intersection of comedy and hip-hop is The Dozens. It’s an insult game that is pretty common in the black community and can be used to contextualize battle rap and diss tracks. The humor of The Dozens is a very wry cutting sort of thing that easily translates to rap.

Black comedy and rap music both have a thing called the Chitlin’ Circuit, and the artists involved often exist in the same space and speak to the same audiences. This is how you end up with Dave Chappelle’s Block Party, In Living Color, or The Arsenio Hall Show and Wild ’N Out in general. If you look at shows like Martin, Living Single, or The Fresh Prince of Bel-Air,  we considered those shows a part of hip-hop culture. They were satire but they documented a part of the black experience in the same way that Ice Cube or Scarface did, and in some cases the shows were actually crafted by rap artists. It’s all black culture, so in a way the two are inseparable because they tap the same source of creativity.

There is a strong relationship between comedy and hip-hop.

They’ve always been intertwined, and in some ways the lines are incredibly blurry. Nick Cannon, Donald Glover, Jean Grae, hell even Yasiin Bey (Mos Def) have done standup before. It’s a symbiotic relationship with a ton of parallels – some obvious and some not so obvious.

When you boil it down, comedy and hip-hop are both just commentaries on the world we live in. Both exist to make you think about things from a different perspective and both require you to have a unique stance on any given subject that evokes some kind of emotional response.

Who are your favorite comedians? Favorite DJs in comedy?

I always dread listing favorites because someone always gets left off. I see a ton of comedy and there are some hilarious new people, but a few of my favorites are Patton Oswalt, Damon Wayans, Eddie Murphy, Maria Bamford, Louis C.K., and Dave Chappelle.

As far as comedy DJs go, I know that Russell Peters gets busy on the decks. Hannibal spins as DJ Burgerfeet – I haven’t seen him DJ yet, and if I’m not mistaken he said he’s not that great at DJing, but he’s probably not as bad as he thinks he is. I’m still trying to convince Wyatt Cenac to do DJ gigs with me as Bartlez N Jamz but he’s not fully on board with it yet. Maybe this article will convince him.

What is your dream gig?

Based on how many hats I wear at the moment I’ve got a few dream gig scenarios, but I think writing comedy is at the top of the list. I’ve got a few music/comedy-related show ideas that I’d love to get off the ground, but developing a show for TV, being in a writer’s room, or even being in the research department for a show would be dope.  

The Seeso version of Night Train came pretty close to checking almost all of the dream job boxes, especially the second season, which you guys will hopefully get to see… hopefully. Being the resident DJ for a show is really cool though, and it’s something that I thoroughly enjoy doing. I wouldn’t mind doing that in a larger capacity as well like The Roots to Fallon or Cipha Sounds to Michael Che.

Not to sound sappy, but in a way my actual life of getting to make/play music and crack jokes is a dream for me because I never imagined that this would be my life. Now, if I could just figure out how to make it all pay more money…

Ana Defillo is a Caracas-born, Miami-raised, NYC-based writer, performer, and Prince lover. You can follow her on Twitter @adefillo.

Meet Donwill, the Indie Hip-Hop Star Cultivating His […]