Sasha Dobson, The TVD Interview

Smack in the middle of an era full of complications—and amidst a year of fear and confusion—singer-songwriter Sasha Dobson has released her four-song EP “Simple Things” that reminds all of us to divert our attention toward what truly matters.

A child of hardworking musical parents from Northern California, Dobson first garnered traction as a jazz vocalist who crafted a sonic and spiritual space for herself amidst New York City’s West Village jazz scene. Sasha befriended recording artist Norah Jones, who recognized a similar musical inclination toward the subtle, nuanced elements of artistic approach that she herself possessed, and together they co-founded the girl group trio Puss N Boots along with Cat Popper.

But Sasha’s rock inclinations were left unattended. A vow to write and write and write was held to, as Dobson devoted herself to the craft that she was simultaneously used to from her upbringing, and coerced into pursuing via her many artistic collaborations as a young artist in California and New York.

“Simple Things,” the captivating four-song EP recently released under her own name, is Dobson’s testament to the potentials of the rock idiom. And it’s a beautiful experiment heralded by the guidance of veteran producer and Blue Note Records label head Don Was who believed in Sasha from day one. A stellar San Rafael session at Bob Weir’s TRI Recording Studios with Jay Lane on drums, Was himself on bass, and Sasha leading on guitar and vocals, resulted in a lovely and authentic product by which to showcase her talents.

You’re from California originally—what brought you to the New York area? Have you lived here for a long time?

I’m a little over twenty years in New York. I spent ten years in Manhattan and ten years in Brooklyn. And I just saw myself cycling into this routine of gigging every night. I was working and I was busy, but I wasn’t building anything beyond that. And I knew that if I distanced myself from the city, that I would only say yes to gigs that made financial sense or that I really, really wanted to do. Because as musicians we’re starving for work, and so you get into this momentum.

I come from a long line of musicians who were eternally overworked. So I moved to Far Rockaway, New York for the beach and the lifestyle, but I actually ended up working more because at the same time, my career opened up more. But I did start really making sure that when I said yes to a gig or project with someone that it made sense. Certain artists like myself who are musicians’ musicians, we burn ourselves out. And I come from a long line of really hard-working musicians, blue collar musicians if you will, like people who work with other musicians and spread themselves so thin. And so for me, I just thought, I think that my life path, aside from singing jazz, is writing music.

Even though it’s not what I set out to do, and even though I fell into it kind of guilty by association—I worked with all these songwriters, I dated and lived with a great songwriter for many years who’s a dear friend of mine. My life has been deeply influenced into this category that it fell into and I needed the space to sort of dive into that. And ever since then, “Simple Things” and the last Puss N Boots record, and my next project—this jazz record I’m about to put out—they’re all a product of making the room to write all the time.

I’m getting a lot of work done. The only real drag, for me, aside from losing all the big tours that we had planned this year, is that my social life—as dorky as it sounds—was also my work. And so whatever isolation that I kind of created by living out here and kind of love—I don’t get to balance it out by going and doing a gig every night or a session. But it’ll pass.

So you had a tour planned around the release of this record originally before quarantine started?

This year was the busiest year of my adult life. I’ve never had so much going on at once. I can’t even believe I have the financial structure to survive this pandemic period, because if it were last year and I didn’t have savings from making a record with Puss N Boots—my band with Norah Jones… we also put out a record this year, which kind of afforded me this project. I really had planned my whole year out. And the universe was like, “fuck you!”

But I’m not the only one; we’re all kind of going through that. I think a lot of us were hoping to have a great year. So you just keep going. On the other hand, my new jazz project was just sort of a trail off of this. You know, you get into a zone with whatever productivity you’re into, and I was just in this really super hustling zone at the beginning of the year, and my jazz band is a big deal for me. That’s kind of like another topic, but it’s something that I think, because I was so fired up about “Simple Things” and that coming together, I just knew that as soon as the tour was over with Puss N Boots, I was going to want to have something else in the mix after “Simple Things.” The point is that if I didn’t have these two projects to work on right now during this pandemic, I’d be just so lost. I have them to focus on and push out into the world, and it could be worse.

How do you see yourself fitting into the New York jazz scene? Did you relate to New York in that music history way with your jazz career at all?

Yeah, I moved to New York in ‘97. My parents are jazz musicians, so I grew up in a family of working jazz musicians. And when I moved to New York, I was initially all about seeing jazz. I didn’t play guitar yet. And I was kind of like a privileged brat in the music world because I had this music support network. We weren’t wealthy, but I was privileged in that I knew a lot of people through my mom and dad when I came out here, and I had sort of a psychic backbone, even though I was a baby and didn’t have a lot of experience outside of working with my family. And I tragically lost my dad, who was a mentor of mine, in a car accident in 2001, so almost twenty years ago.

But it took me a long time to find my way back into jazz in recent years. When I first moved to New York, I was way on the jazz scene and bouncing around in the way that I hustle with people like Norah [Jones] and work in the singer-songwriter world. I was always hanging out in the West Village and always working with jazz musicians. That’s all I did, and so it’s a big part of who I am. And I think then, around the time after losing my dad, it was so apparent that a change needed to happen. I didn’t even want to sing jazz for a while; I mean, I was so depressed.

That was right around the time that Norah and I reconnected. And I was thinking about playing guitar. It just was this joyful thing that I never would have tried if I had still been super in the jazz world, because that’s so elite. This fun and playful thing that I was doing, with my girlfriends, was low key. Sure Norah is a huge star, but when we became friends, we were kids. And we’ll always be kids. When we get together, we’re just girlfriends no matter what’s going on. So it was like this really amazing alternate reality for me to dive into, and it just obviously kind of took off.

So when I started to make records, I was sort of not pigeonholed, but the world started recognizing me as that, and not this thing that I spent my whole life doing. It’s ironic now to come back to jazz twenty years later. I’ve always been doing gigs down in the West Village. It’s just that the mainstream didn’t know that, because I don’t have anything out in the jazz idiom. All these categories—you have to bypass all of the labels and just do what makes you feel really strong. For writing, it’s like whatever you feel you like. As long as I can figure out the funds and get the people together, I’ve enough social resources to bring this energy into this direction.

So that’s kind of what this year has been about, as “Simple Things” is all about my writing, and obviously getting to do this very unique session with these amazing musicians who made it happen. We’d never even played together—it’s the first recording. It was very magical. At least with other recordings I’ve done as a songwriter, it’s normally with musicians that I’d played a couple of years with.

Do you have a favorite jazz vocalist?

When I was growing up, my first love was Ella Fitzgerald; I mean, I am a scat singer—I hate saying that. But my dad was heavy into improv, and that’s a big part of what I do. So Sarah Vaughan, Al Jarreau. But I love Annie Ross, Anita O’Day, and Nancy Wilson. There’re so many.

What was the genesis of the “Simple Things” project—the backstory of how that came together?

I did a record, released in 2013 called Aquarius, which is the first full body of music of my own. I did a collaborative record with a great songwriter and producer, Jesse Harris, called Modern Romance which was about six years before that. And that was more of where I covered his tunes and we co-wrote; it was sort of a debut thing where it was my first non-jazz experience. Then I went on tour with Norah and worked with her and her band and got my shit together on guitar, and then I came back and I had all of these new songs. “Simple Things,” it’s really a brand new body of music. I feel like I’m writing now without the influence of a million people in my life. “Simple Things” is kind of like the first batch of songs that radiates or reflects what my life is now—which is simpler.

Don Was and Jay Lane, who are these amazing musicians, they were there and their support was imperative. But they weren’t in my way. And Don, even though he’s this really well-known producer, he wasn’t in my way. He really just sat back with his bass and he didn’t want to take this on as this big Don Was project, even though his presence was undeniable. He really just stood back and let me do my thing, and I guided the session and brought out each tune one by one. But my friendship with Don has a lot to do with it. We became friends through my relationship with Puss N Boots. Don runs Blue Note Records, and so I met Don through Norah and through getting signed to Blue Note with Puss N Boots, he kind of just became a mentor.

What made the “Simple Things” session unique to you or different from those you had worked on in the past? Did you feel a different energy that made it stand out for you?

Well, never in my life have I brought songs into a recording session with someone on the level of Don Was. And I wasn’t signed as a solo artist—I’m still not signed. I didn’t have an agenda. Don heard me do a solo performance last summer and he just keeps in touch with me and asks what I’m working on; it’s been an incredible mentorship. So I sheepishly invited him to this lame performance I was doing at this gear showcase. And when he showed up—it was hot and it was crowded and I didn’t really want him to hear me, because it wasn’t like glitter and glam. And it wasn’t with my band, you know. But he was there, and I played the best I could—and he loved it. And he said, “I want to record you. I get what you’re doing, man.”

Don pointed out how my jazz singing is there, which I think informs my writing, but the way I play guitar is kind of more like Neil Young—kind of dark. And I was like, “yeah, that’s right!” So he was like, “well, I would love to record you sometime, when we have a day off,” because he’s on tour with Bob Weir when he’s not working at the label. And I just kept hounding him, which I’ve never done. I’ve always been real shy about pushing for things because I grew up in the business, so I never want to end up like I’m another musician who’s got an angle. I’m not a hustler in that way. But this time I was like, “hey, when are we doing this? When are we doing this?” And finally, we made it happen. Don had one day off last September. He said, “we’re going to be in San Francisco, we’re going to be off.” I made sure I was in San Francisco that day. I crashed at my mom’s. And we did it. I just wrote my ass off last summer and I showed up with ten new songs. I’d just never put that much pressure on myself.

It was kind of like “there’s no option but to just do the best you can.” It wasn’t like I had days in the studio, like most artists who get to work with someone like Don. When you have such limited time with someone of such a high caliber you just do the best you can. It was a really incredible experience. I wish I had more time with those guys, but I got those songs. And I figure, “put it out into the world” and it can be this beautiful thing that I did.

Hopefully someday we’ll do more; I’ll always do more. That project was all about actually finishing songs and having a deadline and just doing it. Having that experience in the studio with those two dudes was like… it’s fleeting, you know. I tend to only work with musicians that I know I can grip at for a while; I like to work with people I know, like Norah and I, twenty years. When we go to the studio, our relationship keeps musically evolving. She just sang with me on my jazz record; normally it’s me singing on her record. It’s just an example of how I like working with musicians where our relationship can keep evolving. But sometimes it’s not like that and you just have these fleeting experiences with these people. I guess that’s kind of what “Simple Things” is about.

I was conditioned to think that you could only put out music when you sign. At some point, maybe last year or the year before, I was like, “that’s bullshit.” But there is just something really anticlimactic about putting your own music out digitally and not printing something. When you print it, on vinyl, it’s a whole other thing that then lives and then people buy it. And whether they sell it off to someone else, it’s existing. That’s why vinyl for me is like vintage clothes; it’s one of a kind. I just kind of think that, “Simple Things” will just circulate for a while and it’ll be like this cool thing.

I’ve been trying to keep the jazz project secret, but I’m so fired up about it because I’ve never put out a jazz record. This is the first. It’s a big deal to me. I finally am doing it. I just never had the money when I was really singing jazz. I sort of fell into this identity of being the songwriter.

So what made you decide to release “Simple Things” on vinyl in particular? Are you a vinyl snob or vinyl collector?

Honestly, I don’t know anyone that’s buying CDs anymore. But people are buying records. And I never invested in myself like this. Other people’s records, or the records that were made in my own name, someone else owns. But I had enough money to print this out. I’ve never done this before, and it’s like the most eye opening experience because I’m not a businesswoman. I’m a musician. So it’s interesting taking this on slowly but surely—having these that I released either only on vinyl, or digitally and on vinyl.

I wouldn’t say I’m a vinyl snob; I’m not really a snob with anything. I have records that are older than me, way older than me. I have some records that I’ve had since I was baby. All my CDs are scratched, but there’s something about vinyl that is impenetrable, as far as its ability to withstand time and stay functional.

I want to ask you about “Simple Things”— the recording sessions. It was all recorded live—what was that like for you? Listening to the record, it has this beautiful, small rock club feel to it, a sort of mildly intimate sound that comes across. Can you attribute that to the sessions?

I’m so glad that you could grip that, because it was so grunge. I came in there with my ton of songs printed out, and I was really nervous. I’m in Bob Weir’s studio, and there’s multiple rooms. They put me in this sort of grungy, artsy type vibe room; we were all in one room, and it was specifically recorded like very Nirvana, very garage rock. I’m a jazz singer; I’m used to being isolated, I’m not a screamer. But everybody was in the same room.

I think Don plugged in direct, and we all used headphones, no separation. Jay with his solo drum kit, he just played real quiet but super groovy. I’ve never played with a rock drummer like Jay who could be so intense and never overpower me. And these weren’t songs I was super comfortable playing, they were brand new. It was very one-room, and that’s sort of the sound that you’re hearing of the room, when you listen to the vinyl especially. The engineer who is like Bob Weir’s right hand man, an amazing guy, and he’s always on every tour with Bob, whether it’s the Wolf Brothers or Dead & Company. And he’s one of the best things that came out of the project, making friends with him. I feel lucky.

I think you can hear that, with you and the instrumentalists in the background. They seem sensitive to backing you up, playing with a singer, which is almost a unique skill in itself.

They’ve been touring with Bob for the past two years, who is a very unique artist; he’s not a screamer either. So I basically stole his band for a minute. It worked—thanks, Bob! I was kind of hoping we could get Bob to join us; it was really an ironic day because that day Robert Hunter passed away. Bob ended up having to go and do all these interviews that day, but he stopped in the studio for a minute and I asked him if I could use his amp. And he was like, “oh, sure, have a great time!” He was very, very generous.

“Wanna Be Like You” reminds me of Elvis Costello’s “I Want You” with that kind of murky, volatile sound.

I love the way that one came out; I love Don’s part on that. A sort of dreamy bass. Elvis Costello, I love how prolific he is.

And versatile like yourself—doing different projects.

I love artists like that. To me, it doesn’t seem unfocused, like Dylan, obviously, and Bowie. I was just watching an interview, a Bowie interview, a great Dick Cavett episode. There’s a freedom to not being pigeonholed by a label, but you want support. I want support, because I want to reach as many people as I can, and I know I’m not a businesswoman. I’m not a computer whiz; I don’t understand algorithms. I do know how to play music. I feel like I’m getting a lot better at writing music. I’m starting to understand, there’s something really liberating about just doing what makes you feel super-charged and not worrying about a label.

There’s something really powerful about just doing what gives you energy, whatever inspires you. And there’s something so humbling about doing it yourself. I mean, eventually it’d be nice to turn it over to someone else. But it is kind of profound to see exactly who’s bought your product. It’s like this whole full circle experience scenario, where I would never have known that any of these people from all over the country decided to buy my record. If a label were doing it, I would have no idea. So it’s a good experience for now. But it’s a lot, and it’s taking away from you. There’s only so many hours in the day.

I want to ask you about the title track, “Simple Things.” What was the inspiration behind that? Can you talk about its composition or what that song means for you?

What I recall when I began writing it, as I was staring off into the horizon, sitting on the beach closer to the end of the day—the words “I see signs of change brewing” came pouring out. And I stopped and thought, “and it’s happening all around me.” A couple was playing in the water. A kid was laughing in the sand. I remember feeling like, for me personally, things were maybe going to start shifting. I’d taken a lot of physical and mental steps towards making changes in my personal life and career, but I wasn’t yet on the other side of things like I feel I am now.

Between now and last year, I made a full album and an Christmas record with Puss N Boots, we recorded “Simple Things” and I made the jazz album, all based around the idea that if I really created the space to write, my life would begin to shift around that concept. That’s what’s “Simple Things” is about—shaping things down to the core of what matters. “And the simple things they matter, I can’t think nothing of it / And the distance we created and the closeness we can’t change.” So those two lines are coming from a literal, physical distance but also an emotional or spiritual closeness or connectedness.

It’s so weird how much that song connects with what’s happening right now. I feel like that song in particular, it’s strangely tied in with what’s happening. I don’t know why I wrote it at the end of last summer. I wrote it in my favorite office, which is the beach. I live by a beach, but I kind of go out of my way to a beach that’s way more remote and off the grid; sometimes I take my guitar.

It came out of thin air. I was really hustling last summer, because I thought I had to finish enough songs so that we have way too much music for this session. This one day, you know, and I was trying to finish two other songs that day and “Simple Things” came out of thin air. Being a typical musician, a writer, you need a lot of time for yourself. I’m not just a musician who’s practicing multiple instruments; I’m also a writer. I love to wake up and write and shut the world out and drink coffee for a long time. I think I was dealing with some mild broken heart disillusionment too… things were happening.

Writing music is an interesting process for me. It has a lot to do with attaining this person, or attaining this part of me that I’ve spent my adult life trying to get to. There’s just something so rewarding about writing that I’m just starting to fully realize. I didn’t go to school to be a writer, I just sort of assume this position. But it’s definitely something that I’m sure I’m supposed to do.

Are you planning to work with your Puss N Boots bandmates again in the near future?

Yes. I mean, we’re like lifelong friends and I see us, god willing, like The Runaways—still raging! I’m sure things will pick up eventually with us—at least that’s the thing when there’s a label involved. There’s a certain amount of energy that you sort of get around the release of a record, which I don’t know how much of that was gained or lost now.

But when things are okay again, we’ll book some shows. Norah put out her record, and she lost a huge tour. We lost a number of gigs this summer and maybe a few leading into the end of the year. And then me, all of my smaller shows are built around those shows that I was going to do. It’s so abstract at this point because nobody really knows; it’s kind of hard to just reschedule because we don’t really know what’s going to happen. I sense things will go back to normal, meaning that we’ll be able to come together as one and hang out.