Earlier this summer, I sat down with Dessa—she of Doomtree fame, the 33-year-old perpetually on the Best Rapper in Minneapolis shortlist. Still jet-lagged from a spell in Turkey, Dess spent the afternoon at local haunt Muddy Waters ruminating on the political unrest she witnessed and speaking candidly about her process, her best work, and blueprints for the future. Parts of Speech is out now, as is “.38 Airweight“, the new single from the whole crew.
Where are you going with your solo music?
Part of the reason I went to Turkey was to try to figure that out. It’s easy to get so caught up in the business stuff that it looks more like a video game, you know—how many Twitter followers do you have, how many albums did you sell?
Do you worry about those things?
Well, I do all my own—at least a lot of my own managerial tasks. It is a business, some weeks 90% of my time is business, and 10% is creative. So yeah, I do [worry]. There are very few dividing lines between professional and social, business and creative. My boys are my friends, my boys are my colleagues. I love it, but it’s not very yogi; I’m not finding a work-life balance. You just do it as hard as you can until you fall asleep. But I do worry about the business stuff. I want my music to be shared, and how the business stuff is handled directly informs how many people get to hear it.
Do you find that informs your creative process?
I definitely don’t want it to. So I think I went in part to Turkey to try and Etch-a-Sketch my brain out.
Were you successful?
A little, but I hope I get to keep it. I feel a little more centered; I feel the compulsiveness is gone, to check your phone, to do whatever. I’ve found that, if I’m not attending to my own behavior—say I’m in an elevator—that I’ve opened every window, just refreshing. It’s compulsive. That’s lost time. I think I am hyper-conscious of…time is finite. I can’t get rid of that. I’m going to die. I’m more mindful of how I spend my time than I am of a lot of other things.
I was bothered by the fact that I was in too deep to the internet and to the business stuff, so I went to Turkey in part to disconnect. I’ve disconnected a bit, but it’s only been a few days back. I don’t want to jinx it by announcing I’m cured [Laughs].
Parts of Speech is more song-heavy than, say, A Badly Broken Code.
The thought that occurred to me in Turkey—I don’t know if I’ll take it or not—there have been a few times I’ve felt really frustrated with rap music. One of them was four or five years ago. I was frustrated because I kept trying to write these really literary verses, and they weren’t working. They were too overwrought. Then I wrote a book [Spiral Bound], and I felt so much better about rap. I stopped asking rap to be a book—that’s my book, now I can go write a rap verse. It’s like if I’m in a relationship, and my man doesn’t have a big interest in economics. I’m frustrated with my man, until I meet the right friend. Then it’s all good with my man again.
I feel like that might be the case with music right now, that I’m asking rap to be a lot of different shit that rap isn’t. I’ve considered getting into some other fields pretty hard, so that I’m not asking rap to serve roles it’s not equipped to handle. I took my first classical commissions this summer. The debut of my first chorale piece is in October, at Orchestra Hall. I wonder if that will A) inform me better as a musician in general, and B) free me up a little bit in rap music. Ideally—I don’t know if an artist can pull this off—I want to be someone who can pull off killer rap verses, but who also does great alt-pop songs, and does classical music. And I’ll just be honest about what they all are when they do it.
Doomtree is starting to work on a new crew record, no?
Yeah. We’ve demoed maybe six or seven songs. With No Kings, most of the guys would say we stumbled onto a process that ended up being really quick, in part because we made a lot ill-advised business decisions. We set the release date for the record before we were done, which is a classic bullshit move.
Why did you do that?
I think we were just like, “Fuck, we don’t have anything coming out this year, we’ve gotta get it out.” Part of that is the financial reality of a label, but part is that we were eager to get it out, which is a temptation I think every artist can sympathize with. When you’re in the midst of a creative process…like, I get annoyed with other artists when I hear them do it, then I do the exact same shit. I’ll be in the middle of making a song, not finished by any means, and I’m making the video in my head. “And then there’s this guy with a scepter, right? But the scepter’s made out of candy!” [Laughs]
But you’re still finishing the second verse.
Yeah, I don’t have a fucking song, dude. Stop storyboarding!
So this time, we’re doing it a little bit more by the book. But also, I think we really did strike a vein, in making No Kings. This one has been more short sprints of creative success. We don’t want to push all the way to the finish line and do the whole album in a week.
What’s the actual process like?
It almost always starts with the production. We’ll make a Soundcloud page that has three dozen, four dozen, five dozen beats on it. All the emcees will go and listen, then make notes: “This is great, this is great, this is a maybe, this shit is not tight to me.” Then we’ll just go through and things will naturally line up. There might be four of us who want to do a certain song. You’ll put dibs on things, but I’ve picked three or four songs where I love the beat, but my ass can’t figure out how exactly to ride them [laughs] so at some point, your dibs expire.
What happens if, say, you and Mike [Mictlan] love a beat and want to do it, but the other guys don’t even want the beat on the album?
It’ll be interesting. I’m trying to think if that might happen. Usually, my tastes are just a little to the left of the pack, if I had to guess. But if you talked to everybody in Doomtree, we might all say that. I like the melodic stuff—I’ve got a pop sensibility. Not as a writer, but musically. I like some pop shit. Connotatively, pop can be bad, but denotatively it’s not. Pop doesn’t have to be bad. So sometimes, there are beats I’m stoked on, but then I’ll have the only hand up. That’s probably happened to all of us. You just skip to the next one, because if worst comes to worst, you can always grab it for your next solo joint.
You talked about impulsivity and half-finished songs—but are there any of which you’re particularly proud?
I’m really proud of the choruses on “Call Off Your Ghost”. That was my biggest attempt at a big, pop chorus—it doesn’t feel like some club bullshit, it feels personal. I’m proud of “Warsaw”. There’s a song called “The Chaconne”, that was the headiest song I’d done. The first chorus is about birth, the second is about midlife, the third chorus is death. That’s how the choruses advance, but it’s the same phrasing. It’s really gratifying when, every once in a while, some English prof comes up and asks, “Is that intentional?”
And you use a lot of settings and imagery that wouldn’t be found on many rap records.
I think I was real shy about that at the beginning. I mean…I don’t want to be the nerd of the rap crew. Now, I’m more like, “Whatever conventions you are unwittingly participating in, identify them and burn them to the ground.” But it’s very difficult to know how much of you is native to you and how much has been culturalized.
Do you find that distinction important?
Yeah. I feel like, the first time I heard a rap song that wasn’t in 4/4, I said “I didn’t know you could do that.” The first time somebody was talking to be about Freeway, when they explained “The way he raps is like a palindrome, where the first line rhymes with the last line, second with the second-last.” It’s always “Holy shit, I didn’t know you could do that.” Any time you have one of those moments, I think it’s because someone has realized that there’s a convention they can bow out of. But it’s really hard to realize that. Our assumptions are motherfuckers. They’re the glass that we’re looking at the world through. It’s very hard to focus on the glass itself, or even know it’s there.
Are you doing more print writing right now?
I got a literary agent in New York. I don’t really know what it means yet, but I know it means something. I sent him some work, and he’s submitting it now. Most of my stuff, 65%, is non-fiction. But on [my agent’s] recommendation, I’m doing a little more short fiction.
What’s your aspiration as a writer?
Before I wanted to be a rapper, I wanted to be a writer. I didn’t even know what to do. It’s like, if you want to be an astronaut, what do you do? Stand on the roof? When you’re 19, who’s going to fuck with you? I sent out manuscripts to the New Yorker and the Paris Review and just collected my rejection slips.
Do you still have any of those?
Yeah. I still get them. But then, it got a little easier. Initially I thought “Oh, who the fuck is going to care about creative non-fiction?” But that was my bad, to underestimate the rap community. I think the rap community gets written off as lowbrow all the time.
Even by rappers.
Yeah! People are multifaceted, man. You go to a rave one night, then go to a reading the next day. I was still concerned about whether people would care, but the book went great. It was a best seller at some of the local stores here, and it really encouraged me to stay at it and revive that. To be honest, my long-term goals are in the language arts. They feel connected.
What about education?
No. I do, because I feel it’s important, but I spent some time as a teacher at the collegiate level. I loved lecturing, but I hated grading. And grading is important. Evaluation is important. I just hated doing it. Education is something that I love to visit, but wouldn’t want to live in.
What creative work do you want to have out, tangibly, by the end of the year?
That’s a good question. I want to have the Doomtree record in the bag, whether or not it’s out. I want it done. That chorale piece I mentioned. I’m collaborating with a guy named Andy Thompson here, who has done a really wide variety of work. He’s done stuff with Jeremy Messersmith, who’s a folk artist here, but he worked on the Taylor Swift record last year, too. He and I are working on that chorale piece. I’d like to have at least a couple more prose pieces done and in the chamber for the agent.
How do you hope your role develops over the next decade?
From a career ambition standpoint, I want to share more of my work, better. From an aesthetic standpoint, I like the trajectory I’m on. I hope that I can count myself as genuinely masterful [in a decade] in some of the areas where I feel now that I have talent.
How close do you think you are?
I think in some of them, I’m damn close. I’ve been a little gun-shy of putting in those final thousand hours. I don’t want to sully an idea that’s perfect in my head by manifesting it in a less-than-perfect way. It gets a little easier as you go. Initially, if Doomtree didn’t like a song, I was shipwrecked, emotionally. Because I’d only written eight! That meant they hated more than ten percent of my catalog. Whereas now, I’ve written a lot of songs, and we all have faith in one another’s talent. Years ago, if someone had a note of criticism, it was so easy to catch major feelings. It was impossible to divorce their feelings about a song from their feelings about you as a songwriter.
What about having faith in someone else’s judgment? What if someone says they don’t like a song, but your gut says to keep it?
I think I do that too much. Not that I trust my gut too much, but that I might do well to let people into my creative process a little earlier. A lot of times people will ask to see what I’m working on, and I’ll say “Cool, I’ll show it to you as soon as it’s mixed and mastered and pressed up” [Laughs] I want to present my best work. But that sometimes can make it difficult to present my work when it’s still plastic enough to be changed by the introduction of someone else’s criticism.
Outside of the Twin Cities, outside of your circle, who in rap is exciting you right now?
Some of Kendrick’s stuff was awesome. But I’m due for a new favorite.