Dessa makes music for the masses. If only the masses knew.

Bill Phelps

Midway through a long, discursive conversation about art, hip-hop, pop music, and the craft of writing, MC/singer/songwriter/writer Dessa is told that she had been recently cited as an elite contemporary rapper to a group of young, ardent hip-hop fans.

“I bet they all said, ‘Who?’” she says with a quick laugh.

And indeed, that was the response, which probably says more about the fans than the mercurial artist, who for more than a decade has been one of the most astute and inventive MCs working in pop music, despite flying under the radar of mainstream audiences.


Dessa, who plays the Sinclair on Thursday, released her most fully realized work earlier this year, the beautifully conceived and executed “Chime.” It’s filled with emotionally complex songs that effortlessly cross genres, from tough-minded hip-hop to lovely, hooky pop, without artistic compromise. “Fire Drills,” a strong-willed anthem for the #MeToo movement that sidesteps typical pop sloganeering for sharply defined psychological detail mixing defiance and empowerment, just may be the most powerful song of the year.

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And yet, Dessa, who emerged out of Minneapolis hip-hop collective Doomtree with three intelligent and ambitious records, beginning with 2010’s “A Badly Broken Code,” has yet to get the kind of attention she deserves amid a pop music scene bogged down by repetition, imitation, and mediocrity.

“I don’t know what to make of that,” says the 37-year-old artist, born Margaret Wander. “It would be easy for me to say if I was on a major [label] or well-capitalized my whole life, things would be different and people would recognize the music. This is the reality, and it sometimes confuses me. I could pretend I’m a purist and it doesn’t matter, but as a musician, I want to communicate with as many people as possible. The best part of the job is to be able to share ideas, so you just make the best music you can each time and hope to beat your own watermark.”

“Chime” is the logical outgrowth of her previous albums, with intricate, multi-dimensional hip-hop tracks overflowing with tricky internal and external rhymes, humor, and literary and philosophical allusions, all serving a deeply humane core.

“My point of entry for making music was indie hip-hop, and the best rap lyrics run on allusions, double entendre, metaphors, and wordplay, so when it was time for me to write my own, I had, and still have, a slightly different interest in subjects to create the kind of cultural references I’m making,” Dessa says.


“I spent my teenage years reading Plath and smoking weed, and then by 18, I was studying existential philosophy and being excited by these imaginative, kind of depressed smart alecks who were trying to figure out the world. So the only bells I knew how to ring were those bells, which are different references than a lot of rappers.”

On “Chime,” the hip-hop tracks are mixed with pop-oriented ballads, featuring her expressive singing (her voice has developed a haunted, burnished tone) and deeply involving lyrics about grief, estrangement, and small epiphanies. The shift to more pop melodies and hooks may be a bit jarring for indie purists who want their artists to remain in one box, but these songs feel organic instead of contrived.

“The change in the music here came from my removing the prohibition against pop,” she says. “For a long time, pop was a dirty word in indie hip-hop circles, but I think we all grow up. I grew up musically, and culturally we grew up because we’re more likely to cross genre borders than we were, say, 10 or 15 years ago. And the truth is, I like pop music. I wasn’t going to worry about being exiled from the garden because the record includes some catchy hooks.”

For the last few years, Dessa has been working with neuroscientists on an experimental project to track whether brain imaging could help her fall out of love. (A collection of her essays, “My Own Devices: True Stories from The Road on Music, Science and Senseless Love,” comes out in September.) Ultimately, some of what she learned was incorporated into her music — it informs one of the new record’s best songs, “Good Grief,” among others.

It seems like an extreme way to cultivate material for art, but the good-natured musician has no pretensions about her scientific endeavors. “I’m not trying to be the Bill Nye of the rap world. It was just part of whatever you do for two or three years that’s going to inform two or three songs on an album — it could be moving across the country or the loss of a loved one. That’s what usually ends up in a lyric. But for me working on the science stuff wasn’t, ‘Well what does cortex rhyme with?’ It was more about the big philosophical questions like free will.”


She laughs and adds knowingly, “I frame it as a science project slash art project slash attempt to get over a dude, so even if it didn’t work at all, as a curious person I was thrilled by the idea that there were some legitimate science experiments that seem to substantiate that there are a particular set of structures in the brain that would activate when you’re in love.”

‘As a musician, I want to communicate with as many people as possible. The best part of the job is to be able to share ideas, so you just make the best music you can each time and hope to beat your own watermark.’

All of this is pretty cerebral material, but Dessa makes music for the masses. It’s open-hearted and as approachable as it is challenging. One of these days, the mainstream is going to catch up to her.

She remains optimistic. “I think about Anthony Bourdain. He was unabashedly intellectual and critical and curious, and he always expressed ambivalence while providing a context and frame for opposing cultural ideas, and he made it to the big leagues. That was so exciting to see him win and not be corralled onto a farm team by a risk-averse industry.

“You have to be encouraged by that. And look, Kendrick Lamar won the Pulitzer, so that’s got to give us hope that more curious and demanding work does get recognized and will thrive.”


At the Sinclair, Cambridge, June 28 at 9 p.m. Tickets: $25 and up, 617-547-5200,

Ken Capobianco can be reached at