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Ellie Jackson on outdoor open mics, farm friends and guitar gifts

Mychelyn Schnettler

Singer-songwriter Ellie Jackson has gained quite a bit of notoriety since starting on the scene a few years back through her stellar live shows and her time spent collaborating with Milwaukee musicians like Caley Conway. But scant recorded material — save for a handful of singles and demos in 2019 and one in 2020 — has kept her a bit under the radar.

For many musicians, the past three years have either inspired them to write more or been a creative blur. After a brief release hiatus, Jackson has dusted herself off in 2023 and taken things to the next level with not one but two singles in the past week alone: “Dream Girl” and “Dinner With a Friend.”

She shared the news of both songs via Instagram with a simple message and reminder. “I do believe that music has power,” she said. “It helps us grieve. It helps us celebrate. It can slow us down enough to take a breath or ramp us up enough to move our bodies. … It’s a small gesture that I hope adds a little light to your days.”

Jackson’s songs indeed shine a light, especially in regards to different periods of her own life. She owned a guitar for some time before finally learning to play it, and then only used it to play cover songs, waiting to feel the spark to write her own. “Dream Girl” is the very first song she wrote before she became “electrified” (guitar-wise), and it has circulated in the form of a demo for several years.

The thoughtfully gritty song was Jackson’s toe in the water, taking the reins of songwriting and sharing her perspective with the world. “Dream Girl” is a searing statement on the male gaze — particularly in regards to a female-identifying artist and the role of “muse”, according to Jackson — and is one heck of a first single.

That gave Jackson her start creating songs in her own voice. Soon after, she happened across an Epiphone Wildcat and shifted from acoustic to electric guitar. Gaining an instrument with an electrified element allowed Jackson to expand her sound via effects pedals.

The pop-leaning “Dinner With a Friend'' exemplifies Jackson further exploring her voice as she reprocesses her responses to attachment and rejection in relationships. In turn, she expands her sound with layers of vocals, keys, and a bridging of both acoustic and electric sounds.

Both songs show Jackson’s strengths as a songwriter to always be true to her own story while also working with friends as often as possible. Jackson recorded both songs with Josh Evert at Silver City Studios in Milwaukee and invited a slew of pals to join in, creating a communal feel to her solo work.

While supported by her talented friends, Jackson (who also performs with Milwaukee’s Caley Conway, Maximiano and Old Pup) still brings a distinguished force to her solo work. She anchors her ’90s-meets-modern indie-folk rock sound with gutsy vocals, thoughtful lyrics and plenty of distortion. Listen closely, and you’ll hear those combined influences of current artists like Julia Jacklin, Angel Olsen and Japanese Breakfast mixed with ’90s acts like Fiona Apple and Sheryl Crow.

Jackson spoke with me at the end of summer, just as she was laying plans to release the two songs as a digital 7-inch. We talked about her beginnings as a Milwaukeean and a musician, her unique love and relationship with radio, creating with intentionality, and how a payment plan landed her that first Epiphone Wildcat.

The following interview has been edited for length and clarity.

I’m fascinated to know that you're not from here, and the reason why you came to live in Milwaukee was because of the Riverwest 24 bike race. Is that true? 

So, I moved to Stoughton, Wisc., when I was like nine going on 10. My family all lives in Wisconsin. I went to college in Stevens Point, and I was living in Point for like eight years. I went to college there, and then I stayed after to work at a renewable-energy organization up there.

I was kind of at a place where I was like: “I love Stevens Point. I love the community. I love my work. I love my friends. I could stay here, or I could move.” I was at a crossroads. Milwaukee was attractive to me because of its size and because of all the things I could experience here that I couldn't experience in small towns across Wisconsin.

I moved with one of my best friends, and it was sort of just because it was easier for us to find a place that we could share more affordably. We were looking around the East Side, and [at the time] it was the Riverwest 24 that really sucked me in and made me convinced that Riverwest was where I wanted to be.

I was also really attracted to Milwaukee because I was wanting to be anonymous; I really wanted to move to a big city where I didn't know anyone. The idea of starting over seemed attractive to me at the time, although it was pretty lonely. I really didn't know that many people here.

How do you get into a community and then conversely get into the music scene,and was it music that brought you closer to people when you were still new?

I think I was like, “I just want to go to all the shows.” So maybe it was through, like, super-fandom of all the bands that I was going to see.

Who were those bands? 

Early on, it was the Grasping at Straws. I really liked going to Grasping at Straws shows. I really liked New Boyz Club. I went to a lot of New Boyz Club shows, and Johanna Rose of New Boyz Club has become one of my best friends. But I remember early on, Johanna was like, “You're really fun to see in a crowd. Thanks for coming.” And I just was like … I don't know. [laughs] I just loved all the music happening.

Two women smile brightly while standing on a stone-paved trail with trees and an apartment complex in the background.
Ellie Jackson / Instagram
Ellie Jackson (left) and Johanna Rose.

And I was volunteering with a creative placemaking group who were working on building the infrastructure along The Beerline Trail by Keefe and Richards up to Capitol, trying to connect the neighborhoods of Riverwest and Harambee, which are separated by so many socio-ecological factors. But this trail could geographically connect people, so that was sort of the goal: to figure out a way to geographically connect people and bring people to one place that bridges both sides of the neighborhood. And part of that was through music.

We played films out there, we had big barbecues out there on the trail, and I hosted an open mic. So before I was playing out in Milwaukee, I was hosting open mic on the trail. And it's a weird space. It's like almost a mile of industrial land, so you have to really mean it. If you come, you have to walk like half a mile down a trail at seven o'clock at night, in the dark.

I don't know, you're some kind of weirdo if you do that, and that worked for me. I aligned with and met a lot of people that way. I think that was how I met Justin Otto through his band, The Hatchets. I met Cheston Van Huss, Johanna Rose, Michael Gerlach (of King Courteen) — just like a bunch of musicians who started to become part of my community.

Before you came to Milwaukee, were you playing guitar and singing? Or were you always doing that when you were a kid? 

I got a guitar when I was 18. I didn't really start playing it until I was like 21 because I could play at open mics when I was 21, and I used to just cover songs. I didn't really write songs. I wrote a couple songs, but nothing that I would play [live] — I would cover John Prine and Feist and Iron & Wine. I had half a dozen songs that I would go to open mics and just play occasionally. That was when I was living in Stevens Point.

So you were more into indie folk and classic folk songs?

Yeah. Stuff like that.

From the sets I’ve seen you play, your music is more rockin’ and crunchy.

Well, I got an electric guitar. [laughs]

So you discovered distortion. 

Yes. It was two things. I played acoustic guitar. My dad got me an Ibanez when I graduated high school, and that’s how I learned music and eventually started writing folk music on an acoustic guitar. I feel like I didn't quite realize that, when I’m covering songs, I'm thinking about that person's voice in that song and how they're playing the music. And I think I tried to embody that and tried to replicate that.

It wasn't until Milwaukee and writing and starting to play for people with opinions about how my music sounded that I even considered what my voice was doing. I was trying to emulate some voice, I think, and I didn't even realize I was doing that. So a few things changed: I started singing with my own voice, without putting any kind of effect on it, to the best of my ability. And then I started playing with Caley Conway.

Cheston Van Huss, at some point, was like, “I think you need to play with Caley because you both write from similar places, which is for yourself.” But it took years for me to actually meet Caley. I mean, we met through the music community, but we really got to know each other through farming. We had a volunteer CSA shift together, so we would drive up to West Bend and farm once a week for four or five hours, and then drive back. We would just talk and learn about each other and brainstormed new ideas about music and not about music.

A black-and-white photo of two women looking at the camera with neutral expressions on their faces. The photo has a vintage look to it.
Margaret Muza
Ellie Jackson / Instagram
Caley Conway (left) with Ellie Jackson.

Then, sort of at the end of that growing season, I had an opportunity to play for Jane's Walk Milwaukee. I was like, “Do you want to do this with me?” And we learned a bunch of covers. It was all folk, like Bob Dylan and Joni Mitchell and a bunch of activism-focused music. We did that together, and then we just kind of haven't stopped.

We went on a tour on one of Caley’s projects, I think it was in the winter of 2018. She had released a bunch of Christmas music — some of my favorite Christmas music of all time. Someone on our tour described it as “dystopian snow globe.” We were playing in Rhinelander, and this sweet couple put us up. And when we woke up the next morning, there was an Epiphone Wildcat sitting out, and [the owner] was like, “Oh, I meant to say this last night. If anyone on this tour wanted to buy this, I would sell it for half of what I bought it for.”

I had never owned an electric guitar and had been thinking about an electric guitar. I also had almost no money, so even half of what he had bought it for was, like, insane for me to buy. I had never bought an instrument before. He said he’d let me pay him in increments. I know it was very trust-based. So that was my first electric guitar. After that, I was borrowing pedals from people, and I discovered delay and stuff … distortion. I was, like, 32 or 33 years old. It wasn't that long ago.

I think about that sometimes because I think about who maybe got the opportunity to play with distortion when they were young and figure out different sounds. Electric guitar and effects pedals were like a game-changer for me; it changed the way I write songs. I wasn’t limited to quiet, acoustic music — although that's still very much part of me. Now, I can get loud. I can just express myself through sounds in a way I couldn't before.

That's kind of the hallmark of who you are: Not loud, but I feel like you've got some grit to what you put out there. Where do you pull that kind of influence from? From inside yourself, like something really visceral from deep within? Like PJ Harvey — as one good example of another female musician who really digs in? 

I never grew up with PJ Harvey. There's a lot of music I don't know about, which for me is really exciting because it makes me feel like I might be pulling from some visceral place because it's not like a lot of people who I'll get compared to. I know that they're great, but I don't know their music. Well, a few things. I did college radio. I had a shift as a DJ at Stevens Point.

I've heard about this college station.

89.9, “Your Only Alternative.” And I listened to a lot of different music, but to be honest I did it for so long, and it was such a range. We were just allowed to program so many different kinds of genres, and I did. It was all still analog, and so everything was like CDs and records, and I would just pull from the shelves and just play all sorts of music. I just developed my own sense of taste there.

That was, like, 2005 to 2009 — in that window. [Artists like] Architecture in Helsinki, Iron & Wine and Feist and Regina Spector and … I don’t know, so much I couldn't even begin to tell you. It was years of just pulling from so much music. I don't think I had a go-to. I mean, I had go-tos, but it was like four hours’ worth of go-tos. You know what I mean?

It wasn’t just like, “This is an album I listen to over and over.” It was so much music, and it was sometimes random ’cause when you have just so much time, you have to fill it up. I’d be like, “OK, well, I know I like this section, which is mostly indie rock, right?” Or electronic or whatever. And I'd just pull and play music.

So maybe some of these experiences creep back into your own sound a little bit? 

Yes, but because it was such a range of music for so long, which is such a cool opportunity, I'm not exactly sure where my influences are from. But it's for sure from other musicians. It’s ambiguous.

It's like a wash. 

Yeah. It is a wash of things. But I am really drawn to female vocalists and singer-songwriters. These days, I love listening to Julia Jacklin. I love her music so much. I feel like it’s a combination of really warm and tender, but also it can get really rocking and hard — both of those things.

I also love Angel Olsen. I've been falling in love with Japanese Breakfast more and more. I feel like I sometimes get compared to Mitski. I don't really know her music very well, but I think I like what I know of her. I love Feist so much, and her new music is cool. Her old music is cool. I grew up in the ’90s, so Fiona Apple and Sheryl Crow. I think there was an 88Nine thing where it was like … [pauses]

“Who are my top 50 artists of all time?”

I don't even remember what the question was, but my answer was Sheryl Crow. [laughs] My answer was 1996 Sheryl Crow. Like, if I were on a desert island and I could only bring one album, I think it would be her album from 1996 — her self-titled album, specifically. I think it was last summer, I was driving with Caley and her band up to play in Appleton, and we listened through the whole album again, and I was like, “The tones are incredible. The vocals are incredible. The sentiment is …" I don't know, I just love it.

I mean, Tuesday Night Music Club was the first CD I bought. It’s funny, I was interviewing Alicia [Bognanno] from Bully, and she was describing how she was listening to Sheryl Crow and Jewel and Sarah McLachlan in high school. I was like, “Yeah, dude. I was totally right there with you.”

Yeah. Same kind of zone. It was a good zone.

We’ve talked about how you got to Milwaukee, your influences, how you picked up guitar. Now let’s talk about how you've been cooking up singles and releases on Bandcamp. Sort of quietly, a storm's been brewing. Does this point to a full album?

To be honest, I don't really know when that is gonna happen. But yes, I want there to be a full album. Right now, I have some singles in the works, and I don't have any other albums. This would be like a debut album, I guess, and I'm gonna be releasing these two singles.

Like a seven-inch, basically, right? 

I guess we could call it that.

A CD or Bandcamp seven-inch? 

A Bandcamp seven-inch. OK, that's perfect.

Are the two songs together being issued as a pair purposefully?

I wish. Man, if I could have some intention behind it, that would be great, but it's like my recording has been in fits and spurts. They were both recorded at Silver City Studios with Josh Evert. One is called “Dream Girl,” and one is called “Dinner With a Friend.”

“Dream Girl” is one of the first songs that I wrote, and I think some part of me is like, “I just need to release this so that it can be out in the world, and I can not think about it anymore.” But I think I write differently than I did then, and I just feel like I need that out so that I can kind of move on my own.

But they're both really like sort of higher-energy songs, which I find really interesting, only because I was moved to record them. “Dinner With A Friend” I wrote this winter, and I was like, “I need to record that. I want it to come out while it's still warm out.” I just had this idea of it being a sort of dance-y, fun song for people to listen to. Not that much intention behind why those two songs, except I was just moved to record them quickly.

As a musician, it's so hard. The planning stages of releasing music can be almost intimidating to the point where you just freeze up.

Yeah, I know. So I think it's pretty common for people to often just be like, “OK I need to get these out.”

Tell me about the first song because I feel like that stretches back pretty far, and you said it's something you wrote first. Was it written when you got an electric guitar or before that?  

Before the electric guitar. I wrote it on acoustic guitar. It came from kind of an angsty and fed-up place about the male gaze and just specifically wanting to carve out time to spend with my friends who are all wildly talented, creative, beautiful women. I get why the world would want to give them attention, and obviously I want that for us, but not in an unwanted way. It just made me think about the “Manic Pixie Dream Girl Complex” and how it's been infused in our culture in this way that feels so hard to pull apart from.

Like, where are we allowed to live in an authentic way? Where are we supposed to be a muse to other people? And what if we are a muse to other people? Does that have to be performative, or can we actually just be amazing for the sake of it and not for any other reason and not for any other person? That's kind of what the song’s about.

It must be weird to put your music out there and have everything up for interpretation.

In some ways, I love it. Though the interpretation part … because I feel like I've always heard people say, “When I write a song, it's no longer mine. That it’s up for interpretation, y’know?” I get it more now where someone will tell me after a show, “Oh, I get what that song's about.” And I'm like, “Cool. I'm not sure what you think that's about is what I thought it was about, but that’s great.”

I feel like “Dream Girl,” for me, has been a song where when I play it, people are like, “Is that your song?” I think it's been really validating over the years of playing that song in particular and hearing mostly from women, “Oh, that was a really cool song.” That's kind of what I want, you know? Like, a song for us.

Let’s fast-forward to the new song, “Dinner With a Friend.” What does that center around?

I think “Dinner With a Friend” centers around attachment and rejection and reprocessing my own responses to those things. I think, in some ways, maybe the two songs … and I hadn't really thought about this until now, but “Dinner With A Friend” is very much me, and “Dream Girl” sort of represents this societal larger feeling that I'm observing. Not necessarily grappling with my own self and cleaning up a messy little corner of my mind and trying to figure out why I am the way I am or respond the way I do.

I think a lot of us, if I'm interpreting it correctly, have a lot of social anxiety after the pandemic, and how we socialize was kind of put under a microscope.

I think that's true. I also started therapy, and I think that's part of me grappling — just having the tools and the language to be more self-aware.

I think that's part of it — have a different perspective on subjects that have been sitting there for a while, right? 

I think a lot more of the music that comes to me these days is more that. It's more self-reflective. I think “Dinner With a Friend” is like where I wrote this song … and that's how I feel about that. You know what I mean? Like I just needed that process of songwriting to figure out that part of myself, at least in that moment.

Do you have a set band that you play with nowadays? I know you play with Caley.

I play with Caley Conway. I attribute a lot of why I play to Caley, helping me feel more confident in myself as a musician. I just love playing with femme people and being surrounded by people who embody that kind of level of support. Barry Paul Clark recorded on this. Devin Drobka recorded on “Dinner with a Friend.” Josh [Evert] added to “Dinner With a Friend” and “Dream Girl.”

I mean, to get into the nitty gritty of “Dream Girl,” I was sort of like, “I have so much music to record, but I also work outside of music, and it’s hard to find time to record.” Josh, luckily, is a dear friend of mine and someone who's a dear friend of music in Milwaukee just generally, and is really understanding and easy to collaborate with.

I felt that I needed to get a standing time to come over [to Silver City Studios], even if I didn’t know what I was doing, because I didn’t think I was going to have the capacity to come up with a plan for recording and then show up and execute that plan. I just needed to be in that space and to make something happen, even if it's just one song. That was sort of the goal.

The first day I went into the studio to record, I ended up getting sucked into a work meeting. And I couldn't even do the thing that I meant to, but Josh was there, and Cheston [Van Huss] popped into the studio. Cheston ended up laying down this key line on a slightly out-of-tune piano that's in Silver City, and it sort of gave a shape to the recorded version of “Dream Girl.”

It isn't exactly how I play it live, but I liked it, and I also just honestly appreciated the support of these two collaborators and supporters just being like, “OK, go do your call. We'll just start, then come back.: Y’know what I mean? It was really nice.

Looking forward, what are your plans for the months ahead? Do you have any hopes and dreams these final months of 2023 into 2024?

First of all, I want to say that I've been thinking lately about how there’s no other industry that moves with such a slow, intentional trajectory as music. This is tangential, but I sang on Social Caterpillar’s new album, and I feel like Social Caterpillar is on top of their s***, and it's still something that's coming out months later because of vinyl, because of studio time and because of mixing and mastering.

Ellie Jackson (center) with Social Caterpillar and friends at Cactus Club for the band's album-release show in 2022.
Samer Ghani
Ellie Jackson / Instagram
Ellie Jackson (center) with Social Caterpillar and friends at Cactus Club for the band's album-release show in 2022.

It’s such a slow process. Even when it's fast, it's still really slow. What other world operates like that?

Books, maybe? Publishing?

Just the arts, I feel like. And I think that’s good that we keep it that way. I mean, that’s how you get something intentional, something thoughtful. And that’s even outside of the creation portion. It all takes so long. You could be sitting on songs for like a decade and finally see them come to fruition.

I went to a Milwaukee Symphony Orchestra show, and it was about water, and it’s aligned with the work that I do outside of music. For one of the pieces, they had the composer there, and they were recording that piece for the first time. And it was a 10-year-old piece. And, to be honest, it made me feel great. I was like, “Cool! People who have that level of access to amazing musicians and resources that might come with a symphony orchestra, even they are taking 10 years to record a piece. It takes some of the pressure off from me!”

I've been trying to slow down my own shows, trying not to play out very much so that I can be really intentional and hopefully be less frantic-feeling when it does come time to play out so it can be more enjoyable. And, honestly, I just want us all to have managers and marketing teams and stuff like that. As you know, we don't all have that. So you're wearing a million hats when you're a musician, which I love in some ways, but it also requires me to actually say no a lot because I would have to clone myself to do all the things I want to do.

I've been playing music — singing and playing — with Caley Conway. I've started playing a little with Old Pup. And Maximiano. And I just love singing harmonies. If I could sing harmonies in everyone's band in Milwaukee, it would make me really happy. I also started picking up flute again and have been playing flute a little more, so maybe it's rediscovering some different musical aspects of myself that I forgot about.

Moving forward, I just want to play shows with friends and collaborators that inspire me. I want to play in spaces that inspire me, and I want to be really intentional about what resources I am getting and distributing among my band so that it’s worthwhile for everybody to put on a really great-feeling show.

88Nine Music Director / On-Air Talent | Radio Milwaukee