Every time Dessa appears in Boston, she seems to be passing another milestone. When she came through town in the spring of 2010 as an opener for P.O.S., it marked her first national tour. When she returned in November of that year, it was with the other six members of Doomtree—the first time the whole crew had hit the road together.
Almost a year later, Dessa took to the road again for a quick six-date tour of the east coast. Her November 14th show at the Middle East Upstairs was her first in Boston as a headliner and her first in Boston with a live band.
Touring in support of Castor, The Twin—an album primarily comprised of her previously released material reworked with live instrumentation—Dessa shouldered the mantle of headlining admirably. While she’s always skillfully fluctuated between singing and rapping on stage, it was Dessa’s banter about skinny jeans and singing lessons that showed she’s grown more comfortable with occupying the top of the bill. With fans packed into the many awkwardly placed alcoves of the Middle East Upstairs, Dessa performed much of Castor and her first full length, A Badly Broken Code, while also mixing in other favorites including “Sadie Hawkins” and “Palace.” For an encore, she returned to the stage without the band and covered Leonard Cohen’s “Hallelujah.”
A few hours before her set, Dessa sat down to share her thoughts on headlining, assembling her band and making her next album.
How is the tour going so far?
It’s good. This one is a short run. It’s about a week and a half total, so we’re four shows in and already at the halfway mark.
Is it weird to be just getting started but also already halfway done?
It is a little bit weird, but these shows have been bigger productions so it doesn’t feel like we’re just loading in, rapping and loading out. We take a really careful sound check and we review the set list after each show to talk about what went well and what we can try to be better at. I think if this was a DJ tour it would feel really short, but it feels like a good size for the first east coast run with a live band.
Do you like headlining over opening or being part of the larger Doomtree crew on stage?
Before these runs, I had a strong preference for opening, but I think that was because I didn’t have my sea legs beneath me as a headliner quite yet. I didn’t want to let down the band or feel like I was letting down the club by not making the evening a success. I don’t want to lose anybody money. I don’t want to have an empty room. I don’t want the bartenders not getting tips. After these west and east coast runs, I feel a little steadier on my feet. We had a sell out night yesterday in Manhattan, which felt great. I think we’re going to have a full house tonight. That does a lot to put out some of those concerns.
With your album just coming out, the Doomtree crew record about to come out and the Blowout just around the corner, how did you find the time for this tour?
Touring artists often avoid those summer months when colleges are out of session, so it was kind of a now or never prospect. We knew we wanted to hit the east coast to promote Castor, The Twin. Next week when No Kings comes out, the focus will have to shift to that record so this was our one opportunity.
What’s your set for tonight like? Are you mostly playing stuff that was on Castor?
We’ve got a long enough set that I think we picked all the songs that we can present really well. We’re doing most of Castor, a lot of A Badly Broken Code, and some other songs like “Sadie Hawkins” and “Palace” that were released on the first crew record and the Paper Tiger record, respectively.
Can you give me a rundown on the members of the band?
I’m being backed by a live trio. Shawn McPherson plays standup bass and is also my bandleader. Dustin Kiel plays both guitar and keyboard, and on one song he plays them simultaneously. Joey Van Phillips is on drums. He’s interesting because his dynamic range is so big. He can get really quiet with brushes on snares or he can get really huge, beating the shit out of his kit with huge crescendos. It’s been really fun with the trio to take advantage of the dynamic range that we’re afforded. That’s a harder thing to do with a DJ, because you’re working with music where the big performative choices have already been made. The mix is the mix. The song structure is the song structure. Here, it’s nice to really carefully turn those dials.
Does the instrumentation for the live set match Castor?
Pretty closely. Sometimes it’s contingent on the venue that we’re playing. The day before yesterday the venue had a baby grand piano on stage, so we had the opportunity to use that. But for the most part, the arrangements are the same.
Was your band already playing as a trio when you enlisted them?
No, actually. I had played with Shawn quite a few times over the years, but never as a dedicated project. We assembled the lineup together. I asked Nate Collis, the guitarist for Atmosphere, who he would hire if he was looking for a guitarist and he suggested Dustin. Joey is a guy who has played in a lot of Minneapolis outfits. Some of them are electronic dance music and some of them are jazz standards. We knew that he was a machine and he has a really good reputation in the city.
The last song on Castor, “The Beekeeper” is a single from your next full length. Is it the finished version of the song or a Castor version of the song?
I think it’s the Castor version of “The Beekeeper.” It will be pretty close, but I think I’m going to enlist Cecil Otter to freak it a little bit.
Preorders of Castor came with a short book, Sleeping with Nikki. Was it that you had a book done and an album done and you decided to pair them, or is there a stronger link between the story and the album?
For a long time, I’d liked the idea of including a short book as the preorder gift. I’ve always liked that. When I was little, I would make little books for my little brother out of mailing tape and my mother’s printer paper. Sleeping with Nikki was a story that I had been working on that didn’t have a home in another collection. I thought it would be cool as an exclusive, where only the folks who decided to support by preordering the album got a copy.
A lot of descriptions of you have a lot of slash marks or hyphens—
I think I understand why there are those slash marks and hyphens but it feels less splintered to me. If someone was to describe you like “Tim is a son and a brother and a boyfriend,” those are a lot of roles that you play, but no way does it detract from a centrality of self. For me, all the things that I do stem from the love of language. I understand that they have different names, but they feel intimately connected to me.
Do you sit down to write with a particular format in mind?
Usually, I have an idea and then decide how it’s best expressed depending on the nature of that idea. For example, I’ve been thinking a lot about the relationship between aging and beauty and death. We live in such a beauty-focused culture, I think that it can be tempting to put too large a value on that, which puts you in a position to really start freaking out when you get older and aren’t so beautiful. You paint yourself into that corner, where it really bothers you unduly to see the changes in your face and body. That subject will probably be difficult to explore in a rap song because I need thousands of words. If I wrote a 27-minute rap song, who the hell would want to listen to that? So, sometimes the scope of the idea determines the format. If it’s really brief, it’s a poem. If it’s a little longer, it might be a song. If it’s substantive, it’s better suited for an essay.
How far along is your next record?
I have about nine songs, but I think this album is going to be a lot trickier to record. It isn’t quite like Castor, which is so organic. It isn’t totally like A Badly Broken Code, which is mostly produced sounds. It’s somewhere in between. I know the songs I have so far are strong. I have a good feeling about them. But there are a lot of decisions to be made about how exactly to voice them and how to make them sound just right. I don’t have that much experience in that kind of work yet. I’ve got a lot of sleeve rolling up to do.
Do you think you’re going to try to combine the organic and produced sounds?
The short answer is yes. The long answer is that rather than trying to make an intentional hybrid, now I have a better understanding of a larger sound palette. Now I know how a violin sounds as opposed to a viola. I can distinguish a vibraphone from a xylophone or a glockenspiel. On a producer level, I know the difference between an 808 and EQed clapped snare. So, I like to imagine sitting down and deciding with any given song how it’s best treated. Instead of trying to make a hybrid, I just want to figure out what the song will benefit most from.
Basically, you’re not going to stick to a recipe?
Exactly. There are some songs that are straight up bangers from Lazerbeak where it’s like, “Cool. Done. I’m just going to go in my closet”— that’s where I record my vocals—“and rap.” There’s one that we’ve been reworking a lot—we’ve done maybe seven versions—and now I’m trying to find the right one. We’ve been really trying to freak it so that it sounds just right.
