A sense of humor unlocks the magic of Minneapolis singer-songwriter jeremy messersmith on his latest record Fox/Coyote, named after the tricksters of folklore. Now eight studio albums into his musical career, messersmith has especially embraced his funny bone in recent years. He isn’t afraid to dance silly on TikTok, get flipped off by boomers at his own shows, and he’s even working on a new agnostic gospel album.

During the height of ICE operations in Minnesota, he released a song that weighed in on the crisis with unflinching, and uncensored, directness.

Fox/Coyote is an “easy listening” record inspired by sly humor, but it is also about love and how the experience of it differs as a grown adult. Additionally, it’s a record that messersmith, The Local Show’s July Artist of the Month, continues to cite as one made only possible by the artist-loving community around him. In this interview, the musician shares the ways the Minnesota music scene gives him vitality as an established working artist.

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You have a new album out called Fox/Coyote. You've been a figure of our station since we've been around. This is your first full-length album since 2018’s Late Stage Capitalism. You've released eight studio albums, including a live album and a ukulele album. Bring me up to speed about where you're at right now.

Sure. Well, I just had side-quested for so long in music that I thought I should just make an album. So I had done the ukulele thing. I had done a live album. I did a side project, and finally I was like, "I should probably sit down and write some songs for me to sing." And I didn't really know what those were going to be. It had been a while, and it was like, “Well, what is the shape that I'm in right now as a middle-aged person?” And what is exciting? Is there anything exciting? Are there any midlife narratives that are actually thrilling out there besides getting into pickleball, or running, or craft brewery stuff. Is there anything more than that? I want more.

And the lens that I like the most was I've always had a sense of humor, and the things that interest me the most are the things that I'm amused by, and the things that I find funny. And that's something that I've tried to repress over the years. Because it doesn't really quite fit the loaded-with-feelings singer/songwriter thing, to be cracking jokes all the time. But I feel like it's a little more of who I am, and I was like, “Maybe there's a way that I can lean into that with the writing.” And then be subversive and funny, and maybe just have a good time, and see how that goes. And that's kind of where Fox/Coyote came from.

The classic tricksters of folklore, Fox/Coyote. And then there's the theme of easy listening —

Yes! [Laughs]

Tell me about "Boomers." That one in particular is a standout track, and also was kind of controversial, as I remember following along with you on TikTok.

Yeah, it's a little controversial in that I wanted the song to sound like a mid-tier Coldplay song. ... I was thinking a little bit of the algorithm, where you never know what's going to get picked up by it. But my dream is that somebody who's just — "Yes, I'm very big into this era of Coldplay" — just pops up for them. And then, “Great, this sounds like them,” — until they get to the lyrics and until they get to one line in particular. I'm there for that moment. I want them to have that moment of realization and pivot and either be destroyed or angered or feel something, feel anything, listening to it.

Sometimes that's the worst reaction an audience can have for me, when I'm playing a song, is the nothing. I play "Boomers" and people laugh really hard, and sometimes they laugh really hard and flip me off, and sometimes they just flip me off, and I love it so much. All of it gives me fuel. It's like, “Oh, wow, I made someone feel something. Fantastic.”

You were performing at the Lutsong Music Festival. You were doing just a solo set, and I literally was just hanging out, chilling. And then all of a sudden the audience, out of nowhere, erupted in laughter.

The lead single on this record is "Stallions." Can you tell me a little bit about it?

Yeah, "Stallions" is kind of a love song. Maybe it was inspired by a bit of Taylor Swift. I ended up listening to a ton of Taylor Swift over the Eras Tour thing. It's just in the air, it's in the water.

And I brought it to the band, and I think we were trying to go in a slightly country direction with it. And then my bass player Ian Allison just said, "Hang on, it feels a little bit hokey, what we're doing here. Let's just try this." And he just started playing this little eighth note thing on the bass, and then all of a sudden we were channeling U2 and some stuff that we really love and runs deep for us.

And it just unfolded, and that doesn't really happen in the studio. It can be a bit of a grind with me. I've been told I'm not super great at it. I know what I don't like. I often don't know what I want, but I can tell you what I don't want. And to just have something that seemed very easy, it was just a lovely experience recording it.

And it's also a love song ... Love at midlife feels different than it does in your 20s. And the idea that people work best if you give them space to be themselves. It doesn't have to be this all-consuming fire, and this person is my absolutely everything. Love is just like — it's showing up and seeing what someone actually needs. And so yeah, I guess I related to it on that level a lot too. And I think it's one of the songs that I'm most proud of on the album.

You have maintained such a stellar career as a songwriter and musician over the years. To have gone on for so long and maintained an audience of people who enjoy your music, and to produce this many records that mean a lot to people, I think, is really special. And can you give me some insight into this?

Sure. Well, I think it basically is just part of the ecosystem that I exist in here in the Twin Cities, which is filled with music lovers. It's filled with artists ... Mostly what I do these days is I show up and play at people's houses. That's it. That's my job. I think of it as a high-quality interaction with people, and it also means that I get to know people over the years. If you do that enough, you're in the tap water, you're part of the fabric of the community.

And that's not to say people who do things other ways are not. There's all kinds of different ways to do it. But when you're in the first phase of having a music career, it's kind of like, “All right, I need to get out there, and I need to make my music as big as possible so that it reaches the widest audience.” These days, I'm not so much planting the garden as tending the perennials. So it's a different phase, and it's something I've been very lucky to have here. And that's mostly due to our arts infrastructure here, including The Current.

I'm curious to go all the way back to your beginnings. I know that you were raised in the Assemblies of God church, and eventually found your way out of the church, and now identify as an atheist. Can you bring me back all the way to that turning point? Because I know that was a huge life transition, and it still informs some of the music you make.

Yeah, absolutely. Well, coming out of it for most people ends up being just a confusing experience. I remember telling a friend of mine that it’s like, "I feel like I have a very strong moral compass. It's just spinning wildly in all directions, and I don't know what's what anymore. It's very strange." So, a big chunk of my 20s is just trying to deal with the system that you have imprinted on you as a kid, and then seeing if you can change it to fit into the world that you are getting to know. And it's pretty common, at least for folks who grow up evangelical, to split from that once they leave their teenage years.

And it wasn't one particular moment. I think of it like the time my brother and I were playing darts at home when we were kids. And we just happened to put the dartboard — and we thought it'd be a great idea — we hung it up above the sliding glass doors. And you can guess what happened. My brother threw one, and it hit the glass. And it wasn't like it just shattered … tiny little cracks just started forming until it had spread throughout the entire thing. And it feels a little bit like that.

There were probably 100 different little moments. But overall, fundamentalism is a very rigid belief system, and those tend to be fragile. And any way to play with that system can help break it down with folks. And I think that's part of the reason why I use humor in my writing, is because I still think about reaching people who are in and stuff like that. And humor is a great way to invite people along with you and let them in on the joke.

I have a specific memory of you performing outside of a house to a street full of people. And literally the entire time, I was laughing in between every song. I was with my friend, and she was just looking over at me because I couldn't stop laughing. Your humor just kept speaking to me. I'm also into weird, quirky humor.

Thank God. You were kind of like the audience plant at shows I would call on. I was like, "Oh, thank God. At least one person is laughing at my weird stuff."

Well, I also am the type of person that, when I laugh, I laugh so hysterically ... I don't know how to contain my laughter.

[Laughs] And that's the best person you want at a show. You play the role perfectly.

Through the years, you've always had such great community around you. You do work with the New Standards Holiday Show. You put on a yearly Halloween show, and then you invite awesome special guests. I have a memory of a video that I saw of Ber singing "Bloodsucker." Tell me about finding community and collaborating in that way.

Well, I basically like to play with everyone, and that play can take all kinds of forms. But musical stuff is just, if you have a song, I want to hear it. I host songwriters in my garage over the summers. And that's a chill thing. I [played] with Sadie Gustafson-Zook at the Fine Line at the end of [June].

I love her. I just discovered her.

I was part of her little Tiny Desk crew. And Sadie is someone who's great. You just find people and they're really cool. There's actually too many cool people. Far too many.

Agreed.

Community is everything. Nothing angers me more than when I hear someone talk about the solitary genius or the lone artist who's slaving away doing stuff. I just hate that, and would discard it as a narrative. We are all composite creatures. We are all social animals. And there's this quote that I really like that I say as often as I can, but it's that ideas are generated by communities but articulated by individuals, and I'm only as good as the community that I have around me.

I'm on social media. I'm on TikTok just to see where we are. What are we thinking about? Where's the cutting edge? Oh, that's something I haven't thought about before. And also, if you step out of line as an artist, hopefully the community is going to be there to hold you accountable for that, and to correct you. And if you are part of that community and you can receive that feedback, then so much the better. Everyone is better for that. So yeah, I wouldn't really be much of anything without the artists that live here that I have relied on for years. And yeah, hopefully I'm there to help them out as they help me out.

You have a great presence on social media, because you tell stories, you give advice, you share behind-the-scenes clips. Tell me about using this platform, because it seems to be such a massive tool to also build community farther away. And then also to market themselves.

That's true. I confess, I was a lot more excited about social media some years back. And now it does seem like it is a massive tool, mostly for massive tools.

[Laughs]

Which kind of sucks for a lot of us. But the only way that I can really engage with it is if I'm having some fun. It's kind of like when I do a song-a-day challenge, where I try to write a song every day for a month. I will absolutely bucket that, and I'm like, "I don't want to. I can't write anything today. I got nothing." If I just sit down and force myself to make stuff, I enjoy making things. Social media isn't always the thing, and I do have a fair amount of community coaching from that. Leslie Vincent has helped me out a bunch.

Shout out, Leslie Vincent! She's great.

Leslie is always like, "No, it's not that hard. You just stand in front of the camera and have some text there. Just make sure the lighting is halfway okay." I'm like, okay, all right. I guess I can do that.

One thing that I was delighted by was TikTok started off as just a bunch of teenagers dancing to stuff. And there were dance challenges. And I thought it would be really funny if I did my own dance series, but I'm not really a dancer. I like to move my body, but I don't know anything about it, really. And if you see me dancing socially — no, you didn't. But I sent my song "Huckleberry" from Fox/Coyote to a bunch of dancers and choreographers on Fiverr. And a lot of it is weird scammy stuff, like, "Get your music heard with 100% guaranteed viral dance that will take the world by storm." I'm like, wow, okay, that's a really big promise for somebody. Somebody who can promise all that for only $5.

So I hired a bunch of people from all over the world. And then I started picking places where the U.S. was dropping bombs currently. And then I was sending them $5 to choreograph a dance. And then I would try to replicate the dance as best I could, and it was very funny, because I didn't realize that my body didn't care that I was dancing ironically. I absolutely loved every single little dance video that I made. I was like, “Oh, turns out just moving your body is good for you … Is this the best thing ever?” My mood was elevated. It was absolutely fantastic. So I think one of the things that's gotten easier for me over the years is caring a lot less what people think about me, especially on social media. And I feel more free than ever.

I'm curious, because you've been such a part of our station through live in-studio events, shows, interviews, the whole gamut, basically —

Yeah, I'm on the founding member wall. I remember when it first launched, and I just remember thinking this is exactly the kind of station that we need. I still think about the music that I make, and I'm like, it should be something that The Current would play. That's where I want to live. That's where I want to be.

As somebody who has had such a storied history with our station, can you give me a favorite highlight?

There are so many with regards to this station. Playing Rock the Garden when that was going on. I had this feeling afterwards of, “Well, what do I do with my life now? Okay, I played the big show for my hometown crowd. I guess I need to just go off into the woods now or something.” But I feel like I've achieved everything that I ever would have dreamed of.

And then obviously the big one was the very first time my song "Novocain" ever got played on the radio. I remember driving home from work and hearing Mary Lucia, at the time say, "Next up, we've got some new music that's by an artist I don't think anyone's heard before." And I knew it was me. I was like, “I know that I'm about to get played on the radio for the first time ever on the coolest radio station. Let's go.” And I remember I raced home and turned on the stereo at home. And then the song that I had written in the basement, three feet below where I was standing, was actually going through the airwaves. And that's something that I will just carry with me forever.

Amazing. Yeah, that's something I definitely don't take for granted, as somebody who hosts the radio program that I do, is that I get to give so many people their first opportunity to be played on the radio station. And to see people's little videos of them sharing them get played on the air — it makes my heart soar.

You've got a big Halloween show coming up at the Sheldon Theatre in Red Wing on Oct. 30. You're also working on new music. I don't know how much you want to share, but I'll let you share what you'd like to share.

Sure, I'll talk about it. I am making an agnostic gospel album, Found Jesus. I'm very excited to basically process my sort of coming out of fundamentalism with an album, as so many artists have done before. But this is my take, and it's a little bit different than — I did a little side project called Mixtape for the Milky Way. And that's all very personal, very nonfiction. I don't really perform those songs. And this one is just going to be an absolutely rip-roaring time with a gospel choir and stuff. And it's going to have so many surprise guests on it. It's like a Gorillaz album of vocalists and people stepping in and doing stuff. And I'm still in the middle of it now, so my to-do list is quite long. But I'm very excited for people to hear it when we get it done.