Rapper, singer, writer, and rising empresaria Dessa finds fuel in philosophy.
The brain of Dessa Darling has always been turbocharged by a fascination with language.
Her father remembers his 3-year-old toddler greeting a family friend who stopped by their south Minneapolis house on short notice for the first time in more than a month. “Mark!” Dessa exclaimed. “I haven’t seen you in a fortnight!”
Dessa herself recalls making up definitions for the objects her elementary school bus passed by. “For example, a hydrant might be: ‘hydrant, noun, municipal faucets on corners to be used in case of emergency by authorized persons.’”
Even her name was fair game for wordplay. Dessa was born Margret “Maggie” Wander, but confesses she never felt like a Maggie and imagined different monikers growing up. The one that stuck grew out of her participation in poetry slams as a young adult. Dessa Darling: rhythmically stylish, with a boldness that seems subtly undercut, and thus protected, by a smidgen of self-deprecation.
As it turns out, that’s also a pretty good description of Dessa the rapper, singer, nonfiction prose writer, poet, and teacher. Or, to use her umbrella term, the nationally renowned figure in “the language arts.”
Given that she came out of the U of M with a degree in philosophy (’03), language was always going to pay Dessa’s bills and crystallize her self-identity. And her appetite was always going to be omnivorous, comfortably blending “high” and “low” culture, business and art, ferocity and compassion.
She was a technical writer for a medical device company after college, copping her mother’s wedding ring in an effort to appear older. When a roommate dragged her to that first slam poetry competition, she saw it as a creative outlet, setting in motion the whipsaw similes and razor’s-edge narratives that propelled her to become the lone female rapper in the seven-member hip hop collective known as Doomtree.
Dessa took the lead in professionalizing the Doomtree brand and the Twin Cities-based collective’s business operations, first as CEO and now as president, without dismantling the practice of consensus among members. All have released records under their own names but Dessa also put out chapbooks of poetry and prose, one published by Doomtree, another by the literary magazine Rain Taxi, two others as limited-edition inclusions to the first buyers of her music as a solo artist.
Put simply, she churned on all fronts. The favorite artist of your teenaged daughter as well as the hip tastemakers on Facebook and Pitchfork was suddenly also on the cover of Minnesota Business magazine, signed to teach at the McNally Smith College of Music, a regular on MPR and public television programs, and asked to speak at Mayo Clinic’s Transform conference on innovation and at a Nobel Peace Prize Forum at Augsburg College.
That local ubiquity has led to more rarefied contacts and grander projects over the past year. Lin-Manuel Miranda called asking Dessa to contribute to the Hamilton Mixtape alongside heavyweights like The Roots, Alicia Keys, Chance the Rapper, and Sia, then gushed over her version of “Congratulations” on social media last winter. He also tapped her talents for a benefit song for Puerto Rican victims of Hurricane Maria.
The New York Times commissioned her to write an impressionistic travel story about New Orleans for its Sunday magazine last March. And the Minnesota Orchestra invited her to collaborate with them on interpretations of her music, resulting in two sold-out, well-received performances last April. For 2018, the year Dessa turns 37, expect a book of her creative nonfiction essays from the venerable publisher, Dutton.
The influence of the U
The imprint of her parents is certainly evident in both the work ethic and disparate interests Dessa has cultivated. Her father, Bob Wander, went from being a lute player of 16th century music to a day trader on the grain exchange and then a commercial glider pilot who wrote books and taught others how to fly. Her mother, Sylvia Burgos, is a Puerto Rican who grew up in the Bronx, loves theater and music, and sells grass-fed beef on a farm in Wisconsin while also, until recently, managing communications for a private foundation.
When Dessa was a junior in high school, Wander thought she was taking his dictum—talent x work = output—way too seriously. Dessa has a close bond with her younger brother, Maxie, who was 8 and took it hard when Bob and Sylvia divorced. Dessa, at 14, was fiercely protective. In interviews, she consistently describes her high school experience as that of a loner. Wander saw that she was maniacally competitive on the volleyball court and driven to excel in the International Baccalaureate program at Minneapolis’s Southwest High. But she didn’t seem like she was having any fun and he pulled her aside one day to say it was okay to ease up.
“I wanted her to be happy and well-adjusted, and she was putting so much pressure on herself,” says Wander. “I said, ‘You can step back a little; you don’t always have to be the best.’”
Dessa patiently told her father she planned to be valedictorian of her class. A year later, that’s what happened.
Dessa chose to attend the U because it was urban, the in-state tuition was inexpensive, and it had strong programs in liberal arts and philosophy. Her high school IB program enabled her to shave off a year of credits and she finished her coursework before turning 21. The experience was meaningful enough that she interrupted Doomtree’s first European tour, flying in from Paris one night and out to London the next, in order to give the commencement address at the College of Liberal Arts in spring 2012.
“The brilliant instructors I had at the U are not people with whom I am regularly grabbing coffee,” she says, while grabbing coffee at a Starbucks in Madison, Wisconsin, the morning after a show. “But the world that they exposed to me is the world in which I base my whole life.”
Two stood out. One was Thomas Haley in creative writing. “He was young and hot, so we were all attentive,” Dessa says. Haley unveiled the world of creative nonfiction, a prose form she had never heard of but which was an ideal fit—true-life narratives told with the artistry of a novelist. The best examples came “from a bunch of white guys named David,” including David Foster Wallace, David Sedaris, Dave Eggers, and David Rakoff.
Dessa believes this is the way she wields language best, and searing stories about her brother, her father, and a lover she met while traveling in South America, along with the New Orleans piece in the Times, back her up.
The other, perhaps even more influential professor was Valerie Tiberius in the philosophy department. One day in her Wisdom and Wellness class she put a philosophical theory on the board and asked her students to try to debunk it. Dessa, in full volleyball kill-shot, reigning valedictorian mode, laid out its flaws in a wonderful rebuttal.
“I thought I had ‘won,’” Dessa remembers, relishing the cerebral jujitsu Tiberius had executed. “I think it was a Platonic argument she had put up—I’m not sure—but anyway, I had figured it out, and therefore, at age 20, I’m better than Plato! But then she said the philosopher isn’t here to defend himself so the onus is on us to muster our collective intelligence and actively defend his argument against our critiques. Tiberius called it ‘charitable interpretation’ and it was a phrase and a lesson I knew I would keep in my breast pocket.”
The exercise initiated “a minor but significant shift” in Dessa’s thinking. Her facility with language allows her to be very comfortable with arguments; “they unfold before me like clock parts,” she says. But thanks to Tiberius, she now strives to learn more than to “win.”
One aspect of this shift is that Dessa doesn’t seem to define herself by what she’s against. She believes “it is more honorable to be persuasive than be right, and that happens by understanding the logical or moral through-line of what someone is thinking.” If you can agree on common premises, your ability to persuade is enhanced.
It’s an approach that deepens the impact of her artistry. She’s always going to be driven, but she has mitigated it in the best way possible. She’s a control freak with an inclusive generosity of spirit, a potent combination that helps explain the cultural breadth of her fan base.
The clearest manifestation of this is probably Dessa’s onstage music persona. She cuts a commanding figure—part tomboy Valkyrie, part smoky chanteuse—but tweaks it with heartfelt anecdotes and asides that hint at her vulnerabilities.
At a sold-out show at Icehouse in Minneapolis this past September, she tossed gummy bears to the same crowd from which she accepted shots of whiskey, ceremoniously twirling each glass in a circle around her head before tipping it down her throat. One minute she was shouting, “Let’s start a mother----ing rap show!” and the next she was referring to herself as a gushing soccer mom-type who had abandoned her rap-cool veneer while watching Doomtree cohort Sims play the same Icehouse venue the previous week.
“Where my asthmatics at?” she cried, searching the room for solidarity as she took a hit from her inhaler. “No, I’m not a cokehead, I’m a latchkey kid!”
“I love the dualism between her brute strength and her tenderness,” says good friend and vocalist Aby Wolf, who has known Dessa since before Doomtree and is a frequent collaborator on her projects. “She really tries hard to connect with every member of the audience no matter how big the room.”
The night after Icehouse, Dessa played a block party in downtown Madison. Although she was an opening act, the crowd size and enthusiasm for her performance eclipsed that of the headliner. Performing outside before more than a thousand people, the songs from the stage were delivered vigorously. But there were stark moments of intimacy that sealed the connection.
In one, Dessa stood on the metal fence separating the crowd from the stage. After finishing a song, she was afraid she’d look silly climbing down and demanded that everybody turn their backs and face the Capitol grounds. “I’m not kidding!” she hollered so passionately that everybody knew she was camping it up, but almost everybody turned anyway.
For “Children’s Work,” a wonderfully fragile and intense tribute to the relationship Dessa has with her brother Maxie, Dessa jumped into the audience and asked that everyone with small children bring them down close. Then, she rap-sang to them, her phrases illuminating the night like so many rising Chinese lanterns.
Finally, on “Call Off Your Ghost,” while again wandering into the audience, Dessa asked everyone to sit down and hold up their phones the way baby boomers once used lighters. She delivered the song’s sad, incisive lament about being unable to shake the heartache of a bygone relationship. The phones created a ghostly, campfire glow.
Dessa has sardonically remarked on more than one occasion that heartache is her “niche.” She has admitted to tenaciously loving someone for a decade’s time, long after the relationship had physically ended. It is the one riddle in life she has been unable to parse.
“Perhaps heartache for Dessa is the thing she can’t escape but it fuels her to create something beautiful, like a grain of sand inside an oyster becoming a pearl,” says Aby Wolf.
“Dessa is beautiful and giving and kind, but also pretty complex,” says fellow Doomtree rapper and friend, Sims. “She can also be driven and demanding, and it might be hard to remain in a relationship with somebody that way. We have a good but complicated friendship. There are months that go by where we don’t get along because I can be as uncompromising and foolish—and as thoughtful and kind—as she is.” If so, then maybe there’s hope, because Dessa regards the way Sims and his wife Sarah love and interact as a model for the type of connection she aspires to have.
In the lobby of Dessa’s brain
A highlight of Dessa’s successful shows with the Minnesota Orchestra last April was the clever way she set the scene for “Call Off Your Ghost.” Weeks earlier, she had sent a letter to the U, stating that she wanted to find out from a scientific, physiological perspective why her heartache refused to fade. The result was extensive work with the U’s Center for Magnetic Resonance Research, including MRIs and multi-day studies in which researchers attempted to pin down the exact locations in her brain that induced her heartache. Dessa put up a huge image of her brain scans and referred to it at various points in the concert.
The wisecrack of the performances occurred when Dessa, chronicling her angst, remarked, “Now that I knew where all the love is, all I had to do was take it out.”
Suffice it to say, barring a life-and-death circumstance, no scalpel is getting within a country mile of Dessa’s brain. It’s proven to be a singular source of insight, wit, artistry, and curiosity. And about 13 years ago, for a few terrifying days, Dessa found out what it was like to have it malfunction.
The emergency began when she had an ovary removed, screwing up her body chemistry, physically and mentally, in a manner that medication couldn’t correct.
“My self-concept is very cerebral and language-based because I do all my thinking in words,” Dessa says. “If I had to make a list of personal attributes, my facility with language would be at the top of the list—plus it is what I love doing. So when I couldn’t find words to use effectively and quickly, it felt like more than a rug coming out from under me; it felt like I was sewn to that rug being pulled out.”
It took about a year to feel fully “normal” again.
Since then, of course, Dessa’s brain has roared back with a mighty vengeance. In a short piece for Twin Cities weekly City Pages a few years ago, Dessa herself perfectly described the joy of engaging with that organ between her ears: “It’s a great privilege to report to work each morning in the lobby of my own brain and punch the elevator button that reads Invisible Universe of Ideas.”
The elevator keeps going up.
Britt Robson, once Rudy Perpich’s speech writer, covers the Timberwolves and all forms and styles of music for a variety of local and national publications.