Photos by Scott Streble
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It’s been 14 years since I first interviewed Dessa (birth name Margret Wander) for this magazine. Back in 2009, she was already established as the only woman in Doomtree, the Minneapolis-via-Hopkins hip-hop collective, but she wasn’t too far removed from her roots as a spoken-word poet. She was still the ingénue in her crew, the protégé and ex-girlfriend of Doomtree’s most prominent rapper, Stefon “P.O.S” Alexander, but she was industrious in her ambition, carving out the bookish heartbreaker persona on which she would build her own intense following.
After that first interview, we hosted a variety show together at the Guthrie Theater’s Dowling Studio, pushing her first self-published collection of essays and poems, Spiral Bound. We became friends, and through her I became close with her entire crew, even as she gradually eclipsed them all in terms of popularity.
Propelled by her own unique brand of linguistic magnetism—Dessa can rap, she can talk, and she can write—she became MPR’s darling MC, one of the most recognizable artists in the Twin Cities. Now, at 42, she’s slapped her two-syllable mononym on four full-length rap albums; her own BBC podcast, Deeply Human; a memoir, My Own Devices, published by Dutton, an imprint of Penguin Random House, in 2018; her own ice cream; her own whiskey; and tours of South Africa, China, Australia, and Europe, as well as all of the contiguous 48 states. In fact, just a few days before meeting me for seared tuna salads at The Lowry—just around from her longtime Uptown apartment—she debuted her latest collab with the Minnesota Orchestra, selling out Orchestra Hall three nights in a row, with the second show being simulcast on Twin Cities Public Television.
On September 29, she will release her new album, Bury the Lede, on Doomtree Records. It’s her first full-length since 2018’s Chime, and she’ll be touring the country with her own band to promote it starting in October, with a stop at First Avenue on November 16.
“After this many years of touring, you know where the hot spots are,” she says, with something less than easy confidence. For as beloved as she is here at home, building a following in the rest of the country has proven difficult: Her love for Chicago remains slightly unrequited, they dig her in Seattle but not as much as they do in Denver, and although she’s been living in New York half time since before the pandemic, she’s cautiously hopeful about her show there.
But it’s only when I start asking Dessa questions about the time and the place from which this new batch of songs emerged—in the wake of the dissolution of Doomtree as a working crew—that it becomes truly obvious that she doesn’t see the last few years as a string of unmitigated glory. She starts fidgeting a bit with the silver rings on her fingers while recounting 2020.
In June of that year, in the darkest days of the pandemic, only a month after the murder of George Floyd, Doomtree was at the center of a social media maelstrom regarding a litany of perceived abuses of power by her crewmate, P.O.S. A vocal subset of Doomtree’s followers prodded her into making a short video on social media, where she called out her bandmate. The video went instantly viral, but her words didn’t kick-start any healing, at least any public healing. In fact, they seemed to only intensify the community’s pain. It’s still unclear to me why so much of the social media animus was directed at the only woman in Doomtree, and Dessa is obviously still hurt by all of it, even while striking a posture of defiance.
“Nothing I’ve said seems to have made anything better for anyone,” she says. “But I’m not going to stop making music.”
Trifecta
Three things about Dessa
- Dessa’s mom, Sylvia Burgos Toftness, born and raised in the Bronx, is now an organic cattle farmer in rural Wisconsin.
- In her book My Own Devices, she writes about using a therapy called neurofeedback, which relies on brain wave data from an electroencephalogram, to get over her Doomtree crewmate “X.”
- On The Hamilton Mixtape, Dessa rapped about OG treasury secretary Alexander Hamilton. Later, she rapped about Janet Yellen for APM’s Marketplace.
The lead single on your new album is “Hurricane Party,” which is about partying straight through the apocalypse. It seems to be of a piece with the vibe of the entire album.
I’ve always been a songwriter more than an album writer. But I do think that some of the threads that run through this are sort of an open-eyed existentialism that isn’t entirely pessimistic. I like the idea of a hedonism that doesn’t ask you to disengage from your intellect—like a considered pleasure seeking that involves your mind, too.
It’s surprising how many boy-crazy pop songs are on this album—a string of tunes that all fail the Bechdel test.
Maybe I flatter myself, but I hope some of the pop jams sound infused with…[trails off]. “Blush” is a song about that grade school feeling of love, but it’s checked by loving oneself more. Like, there’s a line I won’t cross, you know what I mean? If you can’t love me sad and you can’t love me angry, then we’re probably not well matched, as much as I might like you.
I know the guys in your crew have teased you forever about the melancholy in your songs being your trademark, but sonically, this really is a fun Dessa album. Lazerbeak told me that this time you were more game to work with him on the beats he offered, to more fully engage within your long-term musical collaboration.
A hundred percent. Yeah.
Why?
I think a combination of being built up and broken down. I feel like I’m more confident now—I’m a professional musician making a living in the field. I think at the beginning of my career, I had something to prove, even within my own clique. I don’t know if it was Beak, but I remember members of Doomtree being like, I wish you’d show us the songs before they’re mixed. Feels a little late in the game to be like, “Hey, do you have any notes?”
So, you wouldn’t solicit their advice until you were on the verge of being finished.
I wanted to impress them, and I didn’t want to show them anything half-baked because I needed it to be as good as I could possibly make it, which very often meant it was far down the process.
You started rapping in your mid-20s.
Early 20s.
A time when Rap Yoda might’ve said, “Too late to become a Jedi, you are.” So, have you always felt like you’re catching up?
Very much so. And, really, I was in a group with some of my favorite artists, so it felt like the standards were really high at home.
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I know you’re still working with Lazerbeak, but we’ve never really talked about what happened in June 2020 with Doomtree. The group was scrutinized as part of an online reckoning over sexual misconduct in the local music scene that went down barely a month after the murder of George Floyd. Three years later, are you guys still friends? What’s the state of the crew?
Some of us, yeah, and some of us, no. I mean, I think there are historical ties that you can’t undo—it’s like the people that you spend your 20s with. And I have so much love for the people in that crew. Our constellations of relationships are as different as they would be even in a sibling relationship—you’re close to some; you can’t get with some all the time. I mean, the whole crew has been together a few times in the past few years, and that’s felt good and important.
What can you say publicly about how that went down and how you’re feeling about it now?
I think that it was difficult to disconnect some of the needed conversations about sex and gender from the ambient threshold of anxiety about public health and from the racial conversations happening at the same time. I’ve never lived through a social upheaval in that way. I think at my most chill and generous, I’m like, “Change is messy, and there is collateral damage as people try to suss everything out.” At my least generous, I’m like, “I think not a lot of care or generosity was shown in trying to make social changes. I think under that much stress, very few people were operating as their best selves.”
There was so much anger and terror in the air.
For me, that was the hardest time of my life, hands down, which includes a stint at a mental institution [in my 20s].
So, you lived through all this inner crew turmoil and pain. Is this album about getting past some of that?
I am motivated by resistance, which I think isn’t that uncommon, right? You’re told, You can’t do that, and you want to go touch the frozen pole with your tongue. I know that I have some of that, which is just like, “I don’t want to go out like this. This isn’t right and it’s not fair. And it’s going to be uncomfortable and I will be publicly criticized, but I’m not going to stop making music.”
Who is saying you should stop making music?
Social media, right? I think I’m driven, and I’m not going to be derailed by Twitter criticism that doesn’t feel warranted.
So, do you regret making the video where you called out P.O.S on Instagram?
I’m bummed that so much of this interview is about that, to be honest.
OK.
I wish I had been my absolute best self and resisted the pressure to respond as quickly as I did. Yeah. To see if I could do something more thoughtfully and fairly.
Did it feel like everything was going to come tumbling down?
It felt urgent.
“I like the idea of a hedonism that doesn’t ask you to disengage from your intellect.”
—Dessa, writer and rapper
You’ve used your voice in so many different ways. In addition to all of your albums, you’ve written for The New York Times Magazine, you’ve written a book-length memoir, you’ve had two seasons of your podcast broadcast on the BBC. What feels like the most rewarding medium for your voice?
I think 10 years ago, there was more pressure to pick a lane. And then for some regrettable reasons—notably, the collapse of a big chunk of the music industry—I think we’re more comfortable with people working in an interdisciplinary way than we used to be. So, it’s not just me. I used to sense the current that I was swimming against in conversation with people who were members of my business team. Like, Hey, you get to be a musician. You can be a writer later, but doing both at the same time would split your resources for either. And now, you see a lot of artists who make music—from Open Mike Eagle to Janelle Monáe—who write for television, who also have podcasts, who star in movies. I think the pressure to really pick a lane and ride it has disintegrated a bit. So, in the intervening 10 years, I think the decision that I’ve made to work across disciplines has become normal. I think there is a distinction between stage work and page work and recorded stuff, but it’s not as much as a retailer would have you think.
How do you earn your living?
I got a great book deal. So, if we were to excise that from the calculation, then live performer all the way. But that one paycheck was a really big deal to me to finance the next couple years of art making.
Are your audiences for each medium distinct from each other?
What do you think?
I think the true Dessa stans are probably loyal across all platforms. So, in all these uses of your voice, what resonates most with you?
It sounds like I’m dodging, but I do think there’s something to the way that your gustatory appetites rotate. I love peanut butter cups, but after three days of peanut butter cups, you’re like, “My kingdom for some quinoa,” or whatever. I think there is an ego return on a room full of people enjoying your work that you most certainly don’t get when you press “The End.” But typing “The End” on a piece that I feel proud of does feel more lasting.
Really?
Maybe I’m wrong in that, but I do feel like the tastes of the music world can be fickle and things can sound dated quickly, and yeah, that can be also true of the way words are used. But I think that the fashions in literature, as far as constructing a great sentence and a great story, I think those change a lot more slowly than the way that we prefer our hi-hats.
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Dessa plays a sunset show in July on the Hewing Hotel’s rooftop.
That maybe explains why you were more willing this time to turn the hi-hat work over to Lazerbeak on this album.
Also, he’s just brilliant. And to be clear, I’ve never written a great hi-hat bar, so I don’t want you to presume that I used to and now I don’t. I just mean leaning in and being like, “Hey, I’m soliciting your feedback. What do you think would be good here?” And also on the stuff that I do well—I mean, Beak works with a ton of mega-talented MCs, so if he’s got something to say about my rap verse, I’d like to hear it. So, I’m taking language input from him there, too. In part because, yeah, I feel like I don’t have to present to him a perfectly cut, finished, polished gem to earn his regard and respect. I respect him, and he respects me already.
You’ve been great friends for 20 years, but it took a long time to find this equal creative footing.
Yeah. I think our friendship developed fast—our brother-and-sisterhood developed quickly on the road, but our relationship as collaborators took a little more time to mature.
You’re not just living here in Minnesota anymore—you’re spending half your time in New York, when you’re not on the road.
I think it was something that I meant to do in my 20s and never got around to. My mom’s Puerto Rican side of the family is out there, and they were always like, “Come to New York.” And I’ve been going since I was a kid, and there had been a homecoming feeling to going to New York even when I was little.
So, is Minneapolis still home to you?
Yeah. I think it’s one of two.
This interview has been edited for length and clarity.
