Dessa showcases her creativity on multiple fronts

She’s a local star with many titles — musician, rapper, author, poet, public speaker — but Minnesotans recognize her by just one name. Dessa.

Those who know the Southwest High School graduate best have watched her develop from a self-conscious 16-year-old to a role model and ambassador for the Minnesota music scene.


But she didn’t make it there on pure luck. Dessa’s devoted following, especially in the Twin Cities, is a product of hard work and several revised drafts.

“I wasn’t very good as a teenager,” she said of her artistic output. “When I read the work I did at 16, and I compare that to the talented 16-year-olds I meet today, my work really sucks.”

That might be hard to believe. As far as her fans are concerned, Dessa is a jack of all trades. Although music is her forte, she has invested her talents in various outlets. Whether she’s working with teens at Minneapolis’ Loft Literary Center or creating her own shade of lipstick that helps educate women in developing countries, Dessa knows how to carry a full plate.

But it all comes back to her work behind a microphone.

Her recent solo record, “Parts of Speech,” is riddled with autobiographical references that showcase a softer, more vulnerable side. A side that contradicts the tough, rugged rapper persona associated with Minneapolis hip-hop collective Doomtree, Dessa’s secondary music project.

Much of “Speech” has a post-break-up, almost Adele-esque feel, revealing a new, self-confessional approach. On single “Call Off Your Ghost,” Dessa purrs, “I don’t think badly of her/I hope she makes you happy.”

Not only is she letting down her defenses, Dessa is looking beyond personal reflection with her music. Many of her new songs beckon listeners to feel comforted — and even empowered — by the lyrics.

The ages-old moving on story told in “Ghost” isn’t just a message to Dessa’s ex-boyfriend. It also allows listeners to make connections beyond the tough-girl facade; to relate to Dessa’s emotional struggles and embrace vulnerability.

This new songwriting perspective exemplifies the ever-changing nature of how to properly harness artistic ability, she said.

“It usually develops over time — for almost every writer. It doesn’t mean you’re not going to be awesome. It doesn’t mean the work you’re doing isn’t strong,” Dessa said.

“Hustle hard, work at it, listen to what readers have to say about it. And avoid the temptation to think that just because something moves you, it moves everybody. It doesn’t.”

For our latest @16 profile, ThreeSixty intern Madie Ley chatted with Dessa earlier this summer about perceptions of beauty, being a role model and why work-life balance (at least for her) is overrated.

What were your high school years like?

During that time, I wasn’t particularly well-adjusted, so I think I ran away from home just briefly when I was like 14. I cut off all my hair and dyed it in the Mississippi River. I was really academically focused, I think because it felt like something I could excel at, something I could control. I wasn’t totally living in my own skin yet, in a social way.

Do you have any regrets about those years?

I wish I had been a little more sympathetic to my mom. I don’t know if I would revise any of my positions in our fundamental disagreements, but I don’t think I realized the power that I had to hurt her. I didn’t realize how much she was hurt. I thought that when she would say that she was hurt, that maybe she was just trying to win an argument, and I didn’t realize how much pain I could cause her.

Have you always wanted to be who you are now?

No. I think I was always really attracted to music and to have a job that had a really public aspect, but my mom was an amazing singer — way better than I am — and I thought that if she didn’t make the cut, then I don’t stand a chance. It was only when I was older that I realized that just wasn’t her ambition. She wasn’t running on that track. It was probably when I was 20 or 21 that I first thought maybe there was some (musical) potential.

You’re known for your solo career and your work with Doomtree. What is it like being the only woman in Doomtree?

I think it’s sort of tough to comment on, because I haven’t done it any other way. It’s like, “What’s it like being the only child?” You can comment on it in a general way, but you don’t really have a point of meaningful comparison. I think if there was a time the novelty of being a woman was at the fore of (Doomtree’s) mind, it probably wore off in the intervening ten years. I do notice that the crowd is interested in that, reporters are interested in that, and I can understand why — there’s not that many women in hip hop. I think it’s a non-issue between us, but I can see why it’s an issue in the larger scope.

What else are you engaged in besides your musical projects?

I’m a writer. I do a little bit of poetry, a good share of creative nonfiction, and I write a column for Minnesota Monthly on philosophy.

How do you strike a balance between all of that?

I don’t. I’m not huge on work-life balance, so I’ll go as hard as I can until there’s a big problem, and then I’ll pull off the acceleration a little bit. I don’t spend a lot of my time figuring out how to craft the perfect cocktail or balance the way I spend my time. I just go hard until something goes wrong, and then I take a break.

Do you have a favorite between any of your non-music endeavors?

I used to say I like creative nonfiction writing the most, but I don’t know. They’re all super hard. I like them, and I feel awesome after I’ve written a piece I’m proud of, but I feel super lousy while I’m writing that piece. It’s very frustrating and slow going — I’m a slow worker. But the feeling of having completed something that I know is good is a feeling you want enough to do almost anything.

In 2011, you worked with the Loft Literary Center on their Teen Writer’s Conference. What was that like?

The Loft was awesome in that they really let me craft a program I felt like I would be good at instructing. I think there’s a lot of youth writing programs where I wouldn’t be an ideal instructor. I’m not the most sentimental youth worker. There are some people where they are like, “I love youth, I love kids,” and I’m like, “I like some kids, I don’t like every person.”

Dessa Parts of Speech
Dessa’s love affair with language has helped her musically — most notably on “Parts of Speech,” her acclaimed 2013 album — and as an in-demand writer and speaker throughout the Twin Cities.

So I said (to The Loft), give me the opportunity to review every application and then a) only pick people whose work I feel like, “I kind of get what that’s going for. I bet I could help get it there.” and b) that exists within a realm of my expertise.

If somebody said, “You know what, I’m really into sonnets,” I’d be like, “That’s awesome, I don’t really know how to write a sonnet.’ I could look it up and figure out how to do it, but they should really kick it with somebody who’s bangin’ at sonnets. So I was able to handpick a group of people whose aesthetic interests were similar to mine, and whose work I thought had promise.

What was your favorite part about working with teenagers?

There was this one dude who was super funny, and he had really good comic timing. It was like almost anything was funny. It’s kind of like old magic, when someone’s really funny, you’ll sit through almost anything. He was really good.

As an instructor, there were a few moments when an exercise I had made up the night before — hoping it would drive home a particular point — worked. “Truth in Letters” was the name of my part of that program. I feel like that was when I landed on an instructional framework. But I was like, “This holds water.” I can take this to other institutions and feel like I’m earning my keep. I can be confident that people who do some of these exercises and really like to hustle at it will leave, genuinely, with valuable writing skills. It’s easy as a student and as an instructor to go through some busy work, but we both know that’s not really helping.

Can you talk about your lipstick project?

There is an independently owned cosmetics company in the city of Minneapolis called The Elixery. They approached me and asked, “Do you want to design a lipstick with your name on it?” And I think my first response was like, “Ooh, fancy!” And then my second response was like, “Mmm, there’s so much messaging about beauty already.”

There’s lots of lipsticks in the world and there’s lots of pictures of pretty people that have been touched up to total falsity. I don’t really know if I want to get into the beauty culture, man. I like to wear makeup sometimes. I’m wearing eyeliner right now. I like how it looks, but I don’t like how important it has become. I was worried about adding my few grams to that side of the scale.

I messaged the proprietor — she’s a super cool chick. She’s a chemist who pours every stick of lipstick by hand, animal-free, cruelty-free, and she sources as many organic ingredients as she can. I liked her as a person. I liked her vibe. We talked about me giving all my proceeds to a charity named CARE who helps with — amongst other missions — (educating) women around the world.

So I said. “You know what, I’m bouncing into it.” I like lipstick, I like the idea that I get to pick one that’s exactly my shade — because I can never find it — and I feel like on the whole I was doing good work. And I really believe in that company. They’re really good people. I was hesitant, and then was won over.

What are your own thoughts on beauty?

I think beauty is entirely too important. On the other hand, I want to appreciate what’s good and pretty and glorious in the world when I encounter it. I think I’m still deciding what my relationship with beauty is. I mean, I went to India when I was five, I cut off all my hair, I stopped wearing makeup — I only wore it in school. But I felt like that was just reactionary to the culture I had found, and what it would have been to participate in that culture.

Either way, I was letting the culture determine how I think about how I look and my impulse to attract a partner — to be beautiful for someone, not just myself — and letting that be formed by the culture I found, because I’m reacting to it, instead of just walking my own lines.

How do you view your role as a white female rapper?

I look white, and I am culturally white. My mother is Puerto Rican, but I enjoy all the white privileges, so that’s a totally fair question. Do I understand that my job is informed by the way I look? Yes. Do I know exactly what to do about that? No. Do I like being told I’m pretty? Yes. Do I worry about becoming too attached to that? Absolutely.

I’ve got a young body for a few years, but I’ve got this mind for my whole life. Ideally, I think I’d enjoy it while it’s here and move on, enjoy the rest of my life with whatever body I live in. But it’s hard. I think you do get attached. We tell girls, “You look pretty!” and we tell boys, “You’re smart, you’re strong,” and yes, that creates problems.


How do you think modern/popular rap music portrays women in general?

It’s hypersexualized, hyper-objectified. I don’t have a problem with hypersexualization, I don’t have a problem with objectification. I do have a problem with that being the only thing there is, with that being so over-represented. I do have a problem when women are marginalized. Which is to say, “Not only are you sexy, but I’m going to treat you like hell to prove I can.” Which is a totally different thing. But yeah, I think it’s a drag. I don’t want there to not be Nicki (Minaj). I just want there to be other people out there, too.

Your recently released album, “Parts of Speech,” sounds like it has many autobiographical elements to it. Can you speak more about that?

I think almost all of the songs that I write that sound like they could be true, are true. There are some occasional flights of fancy or totally obvious extended metaphors. The singles on that record like “Call Off Your Ghost,” I went to a wedding and there was my old boyfriend. And in addition to having an emotional moment there, there was like a secondary radar that went off and said, “Hey, this might not only be a personal story that you’re invested in and you’re freaking out in this moment, but this might also be a scenario that is representative of enough peoples’ lives.”

It was like the art bell went off. Because a lot of times when I’m really moved or bummed or sad or exalted, it’s like no one cares except for me. But then I feel like there’s a second kind of awareness where there’s this chiming bell that’s like, “Oh, there’s an aesthetic potential there, as well.” I think I went to my car and wrote it on a parking ticket, you know, the beginnings of that verse. And that’s true for a lot of the record.

“The Man I Knew” was really about an ex who was using drugs, and doing awesome. Which wasn’t what I expected from someone who started using drugs. And it freaked me out super hard. Both because I didn’t know this dude anymore — he seemed far away — and because a big paradigm was really rattled, just watching him seem to be OK. So I wrote a song about that.

You’re a prominent role model for young girls. Did you have anyone like that when you were growing up?

This woman named Skunk with a bald head, kind of a performative, Grace Jones-type — she was sexy but she was also freaky, like scary. She was existing outside of the pinup kind of role of sexuality. I liked some pop people, too. I liked Gwen Stefani when she was making “Tragic Kingdom” with No Doubt. I liked people like Dorothy Parker, as writers, people like Susan Sarandon were also cool to me. I liked this idea of the “New York intellectual.” That seemed cool to me, I was attracted to that. People with sharp tongues, usually well-dressed, in fitted suits, smoking cigarettes.


  • Profession: Rapper, singer, spoken word artist and writer
  • Name: Margret Wander
  • Age: 33
  • High school: Southwest HS, Minneapolis
  • Find ‘em: On Twitter @dessadarling and