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Dessa embraces pop in new album, Minnesota Orchestra performance

The latest show comes at the heels of a new single and a music video Dessa dropped today from her forthcoming new album, “Bury the Lede,” which will be released on September 29.

Dessa with the Minnesota Orchestra performs Thursday, Aug. 3, Friday, Aug. 4, and Saturday, Aug. 5 at 8 p.m.
Photo by Sam Gehrke

Singer, rapper, and writer Dessa is bringing a “Hurricane Party” to the Orchestra Hall this week. She first performed with the Minnesota Orchestra in 2017, then again in 2018 and 2019, striking an album, “Sound the Bells” based on live performances. The latest show comes at the heels of a new single and a music video Dessa dropped today from her forthcoming new album, “Bury the Lede,” which will be released on September 29. Among them is the upbeat and subversively political “Hurricane Party,” which she’ll be performing at the concert, as well as the emotionally revealing “Chopper.” 

Also airing on TPT this Friday and streaming on the Orchestra’s website, the concert brings together Dessa’s luscious wordplay and danceable tunes with the full richness of the Orchestra’s sound, conducted by Sarah Hicks, the Orchestra’s principal conductor of Live at Orchestra Hall. 

I spoke with Dessa over Zoom from her apartment on the Upper East Side of New York a couple of weeks ago. Here’s our conversation, edited for length and clarity.

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Sheila Regan: What have you got cooking in your final preparations?

Dessa: For these shows, the translation of the songs from their recorded, produced versions to the live stage version with the orchestra— it’s a pretty serious transformation. It’s less like translating a book from one language to another where all the words are replaced than it is like translating a caterpillar to a butterfly. It’s melted and reforged. 

I work with Andy Thompson; he’s the arranger. He melts down the songs to figure out, okay, we’re working with a totally different color palette— how do we want to extract the feelings that we’re looking for with a different set of tools at our disposal? After he finishes arranging the songs, I’ll go in and arrange the vocals— me or Aby Wolf, who I’ve collaborated with before. I’m listening to a MIDI mockup of the songs. I don’t read music, so that means singing each part into GarageBand, and then panning it left and sending it to another singer who doesn’t read music to say, learn all the parts in your left ear, forget all the parts in your right ear, and doing that for every different voice on stage. 

SR: And Aby Wolf will be performing with you? 

D: Yeah, Aby will be there. In past years, I’ve been joined by Aby Wolf and Cameron Kinghorn. He’s also the front person for King Pari and formerly Nooky Jones. And then my two bandmates that I tour with now— Joshua Holmgren and Aviva Jaye, who is a beautiful vocalist who plays the harp, from Brooklyn. Then also Matthew Santos, who I’ve [sung] with in the past and Ashley DuBose. All these people are solo artists in their own right who have kindly agreed to pile on stage together for this night and make a little pop choir. 

SR: Tell me about your new album, Bury the Lede. 

D: It’s 11 songs. And there’s always, for me anyway, this pendular bipolarity, before releasing a record where you’re like, ‘I’m king of the world and also, I’m a total hack.’ And you volley between those two extremes, spending very little time in the middle. I do feel like it’s one of the strongest we’ve ever done, it feels really good. I think as I’ve moved from indie hip hop to pop and some sort of vocal experimental stuff, I’ve always done so apologetically, because I was worried about alienating people who’ve found me through hip hop. The world is different, and I’m less worried about it. The worst that can happen is you don’t like it. And then you go listen to something you do like, that’s not that big a deal. I think I’ve embraced my pop sensibilities without apology on this one in a way that I hadn’t in the past. Pop music was sort of a dirty word when I was coming up in Minneapolis. A lot of those distinctions have dissolved. 

SR: How did it come about originally for you to collaborate with the Minnesota Orchestra? 

D: It was entirely them. I received an email that seemed 100% too good to be true, asking if we might work together. It was so good, it felt fake. And then I went into that meeting, trying to impress: I had a PowerPoint. I figured I had to be extra professional in an effort to meet the orchestra on their terrain. And it turned out the orchestra was totally game to meet me. I was just like, well, I imagine your business objectives for this show are XYZ and they’re like, our objective is to make this awesome. It’s been one of the most rewarding collaborations of my career. 

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SR: I imagine it must be very different rehearsing with the orchestra— who are union and rehearse during the day, and work very quickly– and how it is with the collaborators you normally work with? 

D: Yeah, I mean, you’re right. The schedule is really different. They rehearse earlier in the day together than I would be more likely to with a band. My gig is so nocturnal and I’m sure that clock is sort of internalized. I’ve been doing it for a long time now. My body clock is very much aligned with signing merchandise at nights and a late hotel checkout, if you can get it. That’s not how orchestral players operate. But I think some of the things that surprised me about the way that they get ready is how much prep they do on their own time. And maybe they are doing that late, when they’re at home.

They sometimes rehearse for a show just once. Just a few hours, which is madness to me,That’s probably part of what reading music is. The same way that you and I don’t have to learn how to spell anymore because spellcheck does that for us, they’re able to have this written repository of musical information. When I learn music, I have to get my repeats in to memorize parts, because I won’t be reading anything on stage.

The first time that we started working together, I was apprehensive that I wouldn’t be considered a real musician, because of the genre that I work in and because of how different my skill sets are. And it was really sweet to be welcomed in. And the same questions that I had about the particulars of how they made music like, you make your own reeds every three days? That is insane. They had so many questions about how I make music. Like, that’s so many syllables— when are you breathing? How do you go that fast? They were legitimately curious about it, and that was so sweet.

SR: What have you brought from your work with the orchestra into the rest of your practice? 

D: Some of the most surprising parts of collaborating with the orchestra for the first time were actually bodily sensations. I’m so used to being on stage where there are monitors by my feet. You hear the show from the front coming up at your head from foot level and in the orchestra, all the music is behind you, which gave me the distressing sensation that my ears are facing the wrong way. You have to really tune into what’s happening. 

SR: Can you tell me about the pieces that you’ll be sharing?

D: Some of them will be familiar to people who’ve heard the album that I cut with the Minnesota Orchestra in 2019, which was called “Sound the Bells.”  I picked the favorite songs from that record. We have some orchestral debuts of a handful of songs that people might have heard on rap albums and pop albums, but have never been performed live with the orchestra. And then two new songs. One is “Hurricane Party.” 

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You can Listen to the non-orchestrated version on Dessa’s website.

Dessa with the Minnesota Orchestra performs Thursday, Aug. 3, Friday, Aug. 4, and Saturday, Aug. 5 at 8 p.m. ($44-79). More information here.