Sasha Masakowski
Don’t call Sasha Masakowski a singer. She can sing with an ethereal, angelic sound but she doesn’t think like a singer. She thinks like a composer, arranger, conductor, looper, and distorter. Colleagues have described her as a “live collager” and “sonic architect;” and managers have described her as “difficult to package.” As the sister to experimental upright bass player Martin Masakowski, the daughter of iconic jazz guitarist Steve Masakowski, and visual artist and concert pianist Ulrike Antonie Sprenger, she has had an unusual amount of encouragement to go into the arts, but her path has been solely her own. Sasha has been written up in Paste, OffBeat, Vanity Fair, and DownBeat but she is almost always featured as “a singer.” Even her Wikipedia page describes her simply as “an American jazz singer.” But classic jazz singers generally don’t take multiple BOSS RC-505 loopers, an Elektron Digitakt, and DJ decks wherever they go. Her discography spans an impressive spread of moods and genres across 20 albums. She’s a big fan of collaborations and you can see the artists she admires pop up on multiple projects, in different iterations. She DJs as Tra$h Magnolia, rocks out in Hildegard, and jazzes it up with her family band. We met up on Zoom, between projects, to discuss the release of an upcoming single, the joys of improvising live, and what it’s like to use so many simultaneous looper pedals that you feel like an octopus.
You’ve collaborated with so many artists throughout the years. How do you pick who you’re going to work with?
I love collaboration. There’s so many brilliant musical minds. Everyone is so uniquely their own and finding ways to complement that with my own voices and what I do feels like these really cool musical conversations. A lot of times they’re spontaneous and free. I seek out artists that I admire, who I think it would be mutually interesting to work with. That’s how it happened with Nicholas Payton. I was like, “I don’t know this guy at all.” I’ve said “hi” to him in passing but I knew, so intuitively, that we had to work together and, if we did, it would be explosive. Kevin Scott was another one; Cassie [Watson Francillon] was somebody I didn’t know who sought me out. Now that I’m back and forth from L.A., it’s starting to happen here too, with certain artists where I’m like, ohhh, this is gonna be really good.
I rarely ask the dreaded genre question but the fact that you cover such a scope of them is really exciting.
I’ve had many managers and agents who have struggled with boxing me in. They haven’t known how to market me, where I fit in. They’d be like, “People never know what to expect from you.” I had one agent tell me, “I feel like your career is moving horizontally,” in the sense that I keep growing and expanding and learning new things but not in a useful way to them. I’m happy that I’ve tried to stay true to myself through all of it. You want me to be a trad jazz singer and put a little flower in my hair and sing “St. James Infirmary” all day long? I’m more than that, and I will say that the universe started rewarding me when I started saying “fuck you” to those managers. Nicholas Payton didn’t call me because I sing “Sunny Side of the Street.” He’s calling me because I do electronics, I know how to improvise with them, I make sick beats. That’s who I am, that’s what I do.
I know you’ve got a lot of horror stories and a lot of success stories connected to how many different ways you present yourself musically. Can we start with one of the nightmare situations and follow up with a wonderful one?
Jazz Ascona. I can laugh about it now but, in the moment, I was in the hotel crying. They booked me, as Tra$h Magnolia, to play this pretty conservative jazz festival in Switzerland and I was like, “Do you know what you’re booking me as?” And they were like, “Yeah, we’re trying something new. We want to shake it up and make it more modern and young.” I get there to set up and they have all the seating facing away from me, so I think, “OK, I’m background music.” So I keep it as easy listening, Tra$h Magnolia kid edition, [as] PG as possible. I wrote all these new songs that were more simple, poppy. I prepped a ton for this gig and then, sure enough, 15 minutes in, I’m seeing the owner of the venue fighting with the promoter guy in Italian, and in the middle of a song he comes over and says, “Sasha, please stop what you’re doing!” So I start turning down all my instruments like, “What’s up? What’s wrong?” He said, “Why don’t you just play your ukulele? We have a guitar amp set up.” And I was like, “I’ve never played a ukulele in my life.” They were so shocked, they were like, “We thought you were a solo ukulele act. You need to stop because you’re scaring away the patrons.” So I went back to my hotel so upset, but I was still really looking forward to performing a DJ set on the last day on the main stage, and then they bumped me for a Cajun band that had to go early, so the whole thing was a lesson in acceptance.
MOMs Ball was a good example of a successful one. They actually just wanted a solo Tra$h Magnolia set. I didn’t realize that, and I pushed back ‘cause I wanted the band. I wanted to go into the old Hildegard music that rocks really hard and I wanted to go heavy metal and make a statement with it and it was the right choice. People were talking about that performance for weeks afterwards. People were coming up to me on Mardi Gras Day saying, “Your set was the highlight of my Mardi Gras season.” There’s something to be said for just trusting your gut and taking the risk. I should have maybe put my foot down with the Swiss festival and offered to do a jazz set but told them that my other music was really not a good fit.
When did you start experimenting with electronics?
Pretty much right away. As soon as I started studying jazz music, I was doing both. I guess I was a freshman at UNO, right before Katrina. I was the daughter of a jazz musician but I wasn’t studying it in high school. I was sent to this music conservatory in the Netherlands and I started collaborating with a singer who is a dear friend of mine, her name is Emma James, and she was like, “We should start a band!” It was called OCCO, which stood for “Organized Chaos and Chaotic Organization.” It was a free, improvised thing where it was just her and I and this drummer from Istanbul and a bass player. We were both vocalists who loved exploring the voice as an instrument with range and we really loved spoken word. And then when I got back to New Orleans, I had a band called Free Jazz, Bruh! That was where I started incorporating electronic elements for the first time. I had this TC Helicon VoiceLive Touch [vocal designer and looper] and we used to play upstairs at the Dragon’s Den. And man, it would be packed with people, and I was going so far into being weird and experimenting and climbing up on the rafters and trying to rap. It was so fun and so freeing and that was my introduction into using electronics with a voice and really going into using the voice as an element of sound design. I don’t really identify with singers because I think much more like a producer and an instrumentalist. I like to fit much more into these bands as a soundscape and bring vocal elements that are textural, much more than as a front person. That’s where I’m at right now.
What’s the most portable version of your setup?
It’s probably one [BOSS] RC-505 and the Elektron Digitakt drum machine. I love this device. It’s where I make all my beats. I’ve had it so long that all the buttons are nasty with my finger gunk. It’s such a beast of an instrument. It’s basically a computer in a box and it does so many things. There’s quite a bit of a learning curve and there’s still parameters of it that are over my head that I haven’t even messed with yet, but what I love is you can import all of your own sounds and then you can manipulate your sounds in real time, so it does make it very fun to improvise with. That’s always what I’m looking for when I’m looking at gear: How easy is it for me to be able to perform with this live and improvise with it? I can take a high hat, if it’s on beats two and four, and I can put it on more beats, I can change the sound of it, I can change the filter, the cutoff, I can add delay to it, I can change the tuning of it. It has a lot of versatility in that regard. I really like that you can micro-shift. You can set the parameter to how many times you want it to play a certain thing, so if you have the high hat you can set it to play 100% of the time or 84% of the time and then it kinda humanizes it in that way. You can also micro-adjust the placement of everything ‘cause it’s a sequencer. So everything’s on this grid, but I have this one beat that’s very J Dilla-esque so I have two snare drums: one of them’s way ahead of the beat, one’s a little bit behind, and that’s what being able to micronudge beats within that grid allows you to do.
The only other drum machine that I had, which I still also really love, is called the KORG Volca Beats [analog rhythm machine], which I recommend to a lot of people when they’re just starting off with drum sequencing, ‘cause it’s, like, a $150 little analog synthesizer. And man, the kick drum sound is still one of the best sounds because it’s this fat analog kick that really packs a punch. It’s also really fun to improvise with. You can’t bring your own sounds in—it has its set sounds—but you can mess around with the parameters and add delays and reverb and things.
Photo by Sasha Masakowski
The RC-505 is where all your looping magic comes from?
Yes. I own a few of them and I really started getting to know them during the pandemic because I had this weekly duo live stream gig with Nicholas Payton, live streamed through the Blue Note NYC. So, once a week, Nick and I would get together and I would live sample Nick in real time, so I was taking his instruments, whether it was trumpet, upright bass, synth, or Rhodes. He would run the channels to me. It would come out of me and into the sound board and I basically would live sample him and improvise with the samples as if I was a bass player or a keys player. I would do things like transpose the whole thing into another key and then he’d have to follow me, or I’d drop out and build the kick drum back up. It was a lot of pressure, but after doing it week after week after week, we got really good at it and I got really good at intuiting what Nick was gonna do, catching his phrases, like, “I think this is gonna be a four bar loop as opposed to an eight bar loop, and it looks like he’s gonna want to stack that trumpet harmony, so instead of ending the loop I’m gonna start another one in case he’s trying to harmonize with himself.” I’m clocking it. I kinda always have to be a couple of steps ahead and also, similarly, if there’s a mess up, I’m not keeping that. I’m deleting the loop I just made, starting another one, catching it at the top of the phrase. So many things go unsaid when you’re improvising. It’s just ears and eye contact.
Didn’t the project you’ve been working on with Rex Gregory start out in a similarly improvisational way?
It did. I want to say I had three RC-505 loopers and I was looping Rex’s horn in one of them, his keys in one of them, my own voice in another one, and then I had a drum machine where I was making beats. I had just come from a really beautiful festival that I play every year in Chicago called Instigation, and that particular iteration, I had taken an Amtrak from New Orleans to Chicago, which was amazing. I had a sleeper car and on the way there, I was on the train with all the windows where you could see everything and I was just making beats for hours and hours. I have this whole bank of drum patterns I made called “Amtrak” and that’s what I was using both at Instigation and then in New York, where Rex had met me to record this session. We went into the studio, did a full two days of recording and maybe another day of overdubs. It was Rex and I and a drummer named Aaron Lawson, out of Nashville, who’s amazing. We went in with zero expectations, trying to craft ideas and find grooves that felt really good. It was free jazz but groove based, with a harmonic structure, as opposed to playing totally out there for the sake of it.
That is so many loopers.
It’s a lot. I feel like an octopus.
How many hours of recordings did you guys capture?
It was long—we had 10-to-12 hour days, but it was exhilarating ‘cause we were doing what we love to do. Rex has always been someone I’ve really looked up to musically, artistically. I’ll often say, “I think Rex is New Orleans’ secret weapon.” Even in college, I always thought he was such a musical force of nature. I remember one day we were in the park and he was just sitting there with a pen and paper transcribing [Maurice] Ravel or [Dmitri] Shostakovich. So to have him on this project where he could just let go… I specifically picked him because I love the way his mind thinks about harmony. Most people know him as a saxophone player but I know him for his writing, through various projects like our Bionica days to his record An End to Oblivion. I thought it would be fun to have him more as a keyboard player first, taking over the harmonic structure of the session, which he did [on] piano and synth.
He described you to me as a live collager and said that the two of you really spent time distilling the session into tracks as different stories came out of them. He said, “She completely recontextualized what we did in a way that was shocking and amazing. In one fell swoop, she changed the whole nature of the session and made everything make sense.”
Yeah. That whole record, I probably know every single solo by heart because you have to listen to it over and over and over and wait for the melodies to present themselves. Endless hours of trying to hum melodies, going, “Is this the hook?” voice memoing ideas, and eventually whatever it is starts to just appear… It’s as if you’re taking a massive block of ice and trying to carve it into a really cool ice sculpture. It took a few years. We’re both really busy and have a million projects going on, but I think we gave it the time and the space to let the songs emerge themselves. I’m really happy that we were able to take as much time as we did to complete this project because now I think what we have is something so interesting and so unique sounding. I’ve described it as Little Dragon meets Return to Forever.
I leaned into this project specifically because I know you’re planning to release the first single, “No Witnesses,” later this month, in conjunction with this article and your upcoming birthday. So, can you tell me a little bit more about that song?
I wrote the chorus first and I wanted to get into it with some interesting harmonies. What was cool about that track was that there was a lot of space to fill with vocals. These samples of Rex’s horn set the bed for that and it’s kind of tucked, but it draws the listener in.
To bring it back to one of our first topics, you did something really interesting the night of that Jazz Museum gig. You subtly integrated electronics and quotes from local legends. What inspired that?
[Two Worlds] the record that just came out is intentionally not from “The Masakowski Family.” I wanted to call it “Steve Masakowski and Friends,” even though it’s something that I came up with the concept of, produced, and wrote grants to get funding for. I really wanted to honor my dad ‘cause everyone knows he’s this great guitar player but to me, he’s this genius composer. There’s several compositions of his on the album, and mine and my brother’s, but I wanted to focus on that. They’ll already play his songs at the Bayou Bar, like “Sidewalk Strut” and “Crescent City Jones,” and, to me, composition is the truest form of expressing yourself and what I think will outlive him and all of us. My brother, same, is an amazing bassist but the way he takes all these Middle Eastern influences and rhythmic concepts to the upright bass, and then me, I’m in the electronic, hip-hop world so it’s kinda fun that we can all come together to get behind this one really cool record and make one that just sounds cohesive and good and I’m very proud of that.
The quotes you’re talking about, the first one was from Allison Miner. She was one of the founders of Jazz Fest and a big time mover and shaker in New Orleans, always advocating for artists’ rights. She was just a very powerful woman who kind of got pushed out of the festival and was very upset about it. She passed away very young but my parents both knew her. I learned recently that her birthday is the day before mine and I felt so weirdly connected to this woman and thought, “People need to know her name and hear her voice.” So, when we got booked at Jazz Fest this year I knew I had to work in a quote of hers into this song called “The Real McCoy” by Earl Turbinton, who was known as “the African Cowboy.” [He] was also a legendary modern saxophone player who, if you know you know, but there’s not a lot of recordings or interviews or documentation of him and some of these elders who basically carved the path for what modern New Orleans music is today, so I want them to know that they’re still out here in the ether and we’re still honoring them, shouting them out, playing their music, incorporating their wisdom into what we’re doing, making it known that they’re not forgotten. So I used this Allison Miner quote in the intro of the song: “It’s very important to me that people see music as something that’s a healing force, something that’s not just there to boogie and party and drink to, which, in New Orleans, that has consistently been the way music has been used, it’s been very irreverent…” I also incorporated some Harold Battiste quotes, where he talks about how musicologists tend to get in there and try to pigeonhole things and put labels on terms and, all of a sudden, we start noticing the differences more than we notice the similarities.
For more info, check out sashamasakowski.com.
Top photo: Sasha Masakowski performs as Tra$h Magnolia at Carnaval Lounge in 2022. (photo by Forrest Reiff)
Bottom photo: Masakowski performs at Jazz Fest 2022 as part of New World Order, with Nicholas Payton and Cliff Hines. (photo by Caitlyn Ridenour)
