My name is Jon, and I’m a music nerd. I get really passionate about artists that put their hearts into their work and create music as art and expression, and not just a commercial product. I love to talk about song structure, lyrical feats, and polyrhythms. And on Saturday nights, I tell jokes.
I perform improv comedy with Midnite Show, Voyager, and ComedySportz. I’ve been on stage semi-professionally for a decade, and for even longer, I’ve been a fan of singer, rapper, writer, podcaster, TED Talker, and budding cake maker Dessa. I was first introduced to Doomtree, the Twin Cities-based hip-hop collective of which Dessa is one-seventh, in 2010 and slowly began diving into each member’s solo discography. The group is comprised of strong lyricists and compelling performers, and Dessa sets herself apart with wit, tenderness, and effortless genre-jumping. Lin-Manuel Miranda recruited Dessa to bring life to “Congratulations” on The Hamilton Mixtape, and Senator Amy Klobuchar announced her presidential candidacy in 2020 by walking out to Dessa’s “The Bullpen.”
I’m lucky enough to have gotten the opportunity to chat and raise a glass or two with Dessa over the years, and I bought my tickets for her show on Friday, September 20 at Vivarium the day they went on sale. So when Milwaukee Record asked if I wanted to interview her, I picked my jaw off the floor and jumped at the chance.
Milwaukee Record: What intention do you to bring to your show now as a veteran versus when you were first starting? Does how yourself see you as an artist come into play? Does who you are as a person come into play?
Dessa: I think when I was first starting, the biggest objective was just to tamp down the fear and adrenaline enough to stay cogent—like, don’t lose your feet. Stage fright still plays a role in those first few moments and sometimes the first few songs after a set begins. A lot of my objectives have held pretty steady, even if the way that I achieved them has changed. For me that feels like trying to put on an honest show. Will I recycle a joke on occasion? Sure, of course I have, but I much prefer to try to build something that feels like it’s the product of that particular time and place—to be able to react in real time to something goofy that somebody in the front row does or the drink special that night or whatever just happened in national or global news, you know, whatever might be on our collective minds.
I think I’ve honed that skill as I’ve gotten more reps in, but I think part of the challenging thing is making sure that you are the person that you are presenting—which is so hard because all of us fall into certain tropes or ruts and patterns of behavior. But I want to make sure that I’m arriving on stage and behind a microphone authentically. The way that looks over the passage of many years is going to change. So, I wanna make sure that I’m not larping myself of 10 years ago, you know? Hey, what do you actually feel right now? What do you want to do? What do you want to say? What does the crowd look like? What are the bartenders like? What do the lights feel like right now? And to try to respond in real time to some of those factors.
Photo: Scott Streble
MR: Stepping into a persona but not a character?
D: Yeah, and I would try to say that I tend to strive for a really thin sliver of daylight between my persona and my personality. My persona is practiced at what she wants to say, but I think my personality would still say it.
MR: Do you think that’s something that as you have become more comfortable as an artist has come more naturally? Do you think that earlier on there was a facade, there was this image, and now you’ve kind of become this person?
D: I think that most of us are guilty, even just in daily conversation, of picking and choosing and presenting a self that is more likely to be liked by the audience at hand. And some of that is natural. The language I’m gonna use with my mom at brunch is going to be different than the language that I’m going to use at midnight with friends drinking or something. Some of that’s just being polite and empathetic, but I do think that there can be sort of a speedy, adrenal component of being on stage that lends its own frenetic energy, at least to me. So yeah, early on I was dancing too fast, talking too fast. Because my nervous system is all ramped up on being anxious and excited to be on stage.
MR: Are there things that happen in the audience that throw you off—obviously beyond gross human behavior—like seeing people singing the wrong words or people on their phones?
D: I think more than I perceive myself to be in competition with other artists, I perceive myself to be in competition with the world of other pastimes or human attractions. So yeah, most of us are on our phones a lot, probably more than we wish we were, right? When you get that buzz in your pocket, your hand I think automatically jumps to find out who just texted.
And my job as a performer is to be more interesting than the buzz in your pocket. Is that always possible? No. Like, if you’re waiting for the birth of your first kid, check the screen. But yeah, if I see somebody scrolling on Instagram, or if I see that someone’s making or taking a call, that might be an opportunity to swoop over and take that phone and talk to the person on the other end and turn it into a moment. The thing that I’m most hoping to see is engaged faces. As far as singing the wrong words—and you might not notice this—but when you’re rapping to a lot of people, a lot of people will fake like they know the words.
MR: I mean, I guess maybe I’ve seen that, but I’ve absolutely, definitely never ever done that.
D: Yeah, I guess I have probably done that, too. But from the stage vantage point, you do get to see like how common that is. But yeah, I think for me, people looking anything other than rapt is what I don’t want to see. Like, I’ve got to find a way to send out a lasso, and try to try to do something that makes them eager to get dragged in.
Photo: Zoe Rain
MR: You’re very thoughtful with your writing and deliberate about word choice, but have there ever been times that someone has come back to you and been like, “oh I loved it when you did this,” and you had to act like that’s what you meant to do the whole time? Are there times that fans interpretations have added new dimension to your art?
D: One hundred percent. I think also even more frustrating than receiving a compliment that you didn’t earn, that somebody else sorted out is the accidental homonyms that you didn’t realize might be misheard, essentially.
Even just like, in one song I say ennui, the French term, feeling kind of alienated and melancholic. And everybody, hears it on weed, so it sounds like I’m accidentally writing a stoner anthem when I’m supposed to be, like, on a fainting couch.
MR: How do you respond to the times that you share something during the artistic process that’s maybe vulnerable or necessary for the artistic project, but then maybe you wish you could have that back? Do you double down and own it, maybe don’t mention that anymore, or just straight up lie about it?
D: I think it’s tricky in that, as an artist I don’t have any interest in sharing secrets or sensitive, vulnerable stuff for the sake of exhibitionism. But I think that sharing tender, personal, important stuff can lend stakes to a song, because very often that’s the stakes of our lives: the private moments where we’re frustrated or we’re hurt or we feel like we’ve messed up or we’ve been abandoned whatever—those are some really salient parts of our lives. And so in some ways, I feel like I have license to mine my own private personal life for songcraft, in part because that’s the only life that would be available to me, meaning I don’t want to run around and tell other people’s stories. The tricky bit is that I think so few of our secrets happen in isolation. So there have been times when I’ve written a song, I’ve definitely sent it to the people it’s about in advance to ask, “Is this cool?” These are not songs that use their names or anything, but they could reasonably recognize themselves in the song even if a random listener couldn’t.
I know that there’s been at least one song that was insufficiently anonymized, so you know, I changed features of this character, but that character was still recognized, and yeah, I felt horrible about it. That was a lesson I wish I didn’t need, and I certainly wish I hadn’t hurt somebody’s feelings, and I think beyond that point, it’s an apology. But after a song is released, it’s pretty tough to put toothpaste back in the tube. The feelings about it are mine and I have license to share, but that doesn’t happen in a vacuum. The circumstances are shared, which they almost always are.
MR: Let’s talk about cakes! I’ve been amazed by your cakes that you’ve been posting on social media. Tell me about your artistic passion for cakes.
D: Totally blindsided. You know, I think I have not historically been a particularly gifted in the kitchen, generally. Passable, and that’s kind of it. But I lost my voice at the very end of 2023 and ended up with a bunch of time on my hands. I wasn’t speaking at all, which was a first. It was the holidays when the music industry closed us down, and I’d recently baked a couple of cakes, then really dug in. So I had time to like fully rabbit-hole. I don’t think I have ever discovered a passion as abiding as an adult. I went and watched a fufillion YouTube tutorials on how to make photorealistic buttercream flowers.
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These are sculptures, essentially made in buttercream, where you’ve got sepals and petals and interior folds and, you know, all varieties of leaves and vining, and, like, all of a sudden, I found myself as a crazy student of botany. Now I’m stopping in every bodega in New York to try to figure out, “okay, this is the center of a gerbera”—flowers that I didn’t even know the names of—and “where does scabiosa grow?” And I follow bunch of Korean buttercream artists. They’re the best. They use a particular kind of buttercream that’s rarely used in the U.S. And yeah, I dream about it. I go to bed thinking about cakes, and I wake up thinking about cakes, which is also just like hella-culturally confusing because I live my life as a rapper in combat boots. But yeah, man, we contain multitudes.
MR: You’ve worked with Lin-Manuel Miranda, and I remember seeing Jordan Klepper pop up in a Doomtree fan video at one point a number of years ago—can you talk about what it’s like meeting people that you respect that are fans of your work?
D: Generally on the topic of meeting celebrities—artistic celebrities—I admit I get pretty weird. And I get weird in the completely pedestrian and predictable ways, which is my least favorite way to get weird. I get a little nervous. I worry, “Am I being cool? Not just “Am I being normal. Am I being cool?” It feels like very seventh grade, you know what I mean? It’s those junior high feelings.
So the first time I was at like a fancy dinner party, I got to sit next to Yo-Yo Ma, and I was so excited. He said something nice about a science presentation that I had recently done, and I was just so stoked to talk to him. I wasn’t sure, like, at what point I was monopolizing his time. So then do you just bail on a conversation midway through like a weirdo? Or at what point do you seem careering, right? That also makes me really nervous, where I’m worried that the more famous person thinks I’m trying to shake them down for a feature, which of course, I would love—if you would like that, I would love to. So how to naturally have those conversations with people in generally the same industry, I don’t know. I think that is a moment at which my social graces are at a career low.