Flipping It on Dessa

Notables at the Nomad Puts Dessa in the Hot Seat

By Gabriel Douglas
Photography by Brian Kaufenberg
Gabriel Douglas interviews Dessa // Photo by Brian Kaufenberg

Gabriel Douglas interviews Dessa // Photo by Brian Kaufenberg

Dessa. She is an artist. She is a wordsmith. She is in a hip-hop collective called Doomtree. She hosts a TPT & MN Original TV show called The Lowertown Line. She’s into hoop earrings. She’s reading poets you will learn about years after she has devoured all they composed. She does what she loves for a living. Every day. Inside and out. 

Rapping. It’s become the profession for which she is known. “Baggy jeans, extra large shirts,” she said of her early stages of being a performer in the hip-hop world. Growing into her own skin has made her very self-aware. Not wanting to be the “girl MC,” she made a point to dress the opposite. She now wears what she wants, rather than what she wore in the early days which served as a diversion to her gender.

“I don’t have any hobbies.”

Dessa Deep In ThoughtWhen taken out of context, that’s a startling statement coming from Dessa. It could signify a very bleak, desolate box of rare after-hours adventures and weekends off. But hearing her talk about prose and songs—all the things that envelop her spirit—it makes sense. Words and rhythm don’t get the luxury of taking any moments off, much less days off, in her wheelhouse. She lives and breathes her work. She worked up to this point and she smiles often when talking about it. She does what she loves and when there is time left over, the words and rhythm get extra attention. She writes, rewrites, and analyzes all things music. There is no work/play dynamic to be fiddled with. Immersion in her passion is what drives her.

And though she doesn’t have hobbies, she puts in the time for things she cares about. She helps people. She offers an ear to people in prison. Dessa has her own lipstick. And not just any lipstick, but a rich, matte-red lipstick from Elixery, whose profits benefit a charitable cause hand-picked by Dessa. She brings real talk to detention centers. Her whole crew, Doomtree, brought their talent and energy during the whole month of March to the Roosevelt High School. “Sometimes, it’s as simple as lending an ear and telling them [that] what they have to say is important,” Dessa said, referring to the understated art of listening intently and actually giving a s**t.

The conviction of caring goes a long way—it’s seen in every decision she makes. She researches, fact checks, then dives head-first into her charitable causes (I had the honor of sharing the stage her at a benefit for the South Side Nurturing Center).

Hailing from Uptown these days, Dessa is a city woman through and through. She believes in the power of “local,” and it is evident in the choices she makes. You can still catch her at many local establishments working on some phrases, Pricelining some swanky hotels for her next run of shows, or catching up with a friend. What should you do if you find Dessa on the town? She’s happy to share a moment and give you her time.  She’s worked toward having an active audience for a while now, so being spotted isn’t something she renounces. But she also knows that those close to her didn’t ask for the attention-split when they leave the house with her. If she’s heavily engaged in a conversation, just send the whiskey anonymously. Your Instagram can wait.

Dessa and Gabe // Photo by Brian Kaufenberg

Dessa and Gabe // Photo by Brian Kaufenberg

So she has no hobbies and she’s helping all these people. Does she do it all single-handedly? She’s definitely the driving force in all things Dessa, but there is a whole network of gurus and well-to-do’s  that assist her in creating. Collaboration is an integral part of her sound from beats (many rhythms hammered into existence by the beat-maker extraordinaire Lazerbeak), to the live band (headed by Sean McPherson from Heiruspecs), and guest vocals (look for Aby Wolf throwing down a harmony). The network she has surrounded herself with is a testament to how seriously she takes her livelihood. She is quick to sing praises of all her band members, promoters who have helped her along the way, and anybody who merits a job well done.

For eight years, Dessa has been creating her own concoction of intellectual hip-hop (there’s still not an easy way to describe her spoken word prowess, while incorporating her raw, aggressive MC-swagger without completely missing the mark). She’s ready to drop her new album, Parts of Speech, in June, which is slated to have 12 tracks. It dives into both the high-level studio production of her previous album, A Badly  Broken Code, and the energy of real-time musicians she captured on Castor, the Twin.

Dessa answers Gabriel's Question

Dessa answers Gabriel’s Question

She’s done solo runs, crew runs, and recently has been bringing her live band on the road. So many factors go into what can make a successful show. The possibilities of a tour actually making money are becoming harder and harder to come by. How can you help independent artists?

“Preorder. Pre-order, pre-order, pre-order. With my new record coming out, that makes the difference,” Dessa urged.

“You can get to six feet high on a trampoline with two 3-foot jumps, or you can put it all into one six-foot jump. You get higher, more people can see you,” she said, explaining the pre-ordering system in the music world. Pre-ordering an album can give an up-and-coming artist a needed extra boost in the world of charts, numbers, and algorithms which can quickly smolder a release (low sales), or stoke the fire to keep the album ablaze (high sales). Dessa and her Doomtree crew have always been pioneers in incentives for pre-ordering from their catalog: when the No Kings album was released, they gave away special edition t-shirts, boxes, and pins. They even had some baked goods for fans scoping out the album around town.

How does Dessa write so well? She lives it. She breathes it. She conceptualizes it. She nurtures it. And whether it’ll be a full, live band onslaught or the pages of a book, you can bet I’ll be ready and waiting for the next chapter in the life of Dessa.


nomad-logoThanks to the Nomad World Pub for their support. Visit the Nomad World Pub every Wednesday when a special craft beer goes on tap for Mid-Week Beer Geek.

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