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20 Questions: Greg Freeman

The singer-songwriter wanted to separate himself from his songs. He couldn’t—and so he made one of the year’s most candid records.

20 Questions • October 15, 2026
20 Questions: Greg Freeman
Gabe Long

Greg Freeman has bars. 

“Is your life just appetites/or a menu with no way to order?” he asks a few minutes into his third album, All Set the Bone. “Life hits quicker than doubt/And regret fills the cracks like grout,” he reckons a little later in a song about a teenage car crash and the precarity of any life lived at all. And then: “You got to do something with all that shame/And give your fear a proper human name.” These three potent bits come only from the first three songs on a ragged 13-track indie rock epic that wedges hard bits of wisdom inside scenes so vivid you may wonder if you’re seeing them, not simply hearing them. 

Freeman first broke through last summer with his second album, Burnover. It slid neatly into the spaces between indie rock and alt-country, seemingly in league with MJ Lenderman and Wednesday, Florry and even Big Thief, bands echoing assorted ratios of Jason Molina and Neil Young, Sonic Youth and Silver Jews, through very personal visions. But Freeman never seemed altogether comfortable with that label, pushing it off in interviews as a tag borne of laziness.

All Set the Bone pushes it off even more. Sure, Freeman’s voice still has the same keening country quality as Molina, and there are a handful of riveting guitar solos and primitive rock outbursts. But he climbs into country-soul during “Costs,” gets wonderfully aggressive during “Hail Mary,” and drifts into ascendant electric psychedelia during the glorious “Withdrawn.” He brings a bruised but perseverant perspective to it all, like he’s seen the worst of life long enough to fully fantasize about what the best could be, like a long-thirsty person finally imagining cool water.

Alt-country? Maybe? Indie rock? Also maybe. But unequivocally one of the year’s best rock ’n’ roll rides from a songwriter who stuffs verses with unexpected linguistic shifts and miniature emotional epiphanies and lands sharp hooks even when he resists the safety of dependable song structures. Freeman spoke to Playboy from home in Chicago, soon after waking up on the morning he released All Set the Bone.

Good morning, Greg. Your third album, All Set the Bone, has been out for a few hours. What’s your release-day ritual—or at least your plan?

I just woke up, so I don’t know what I’m going to do yet. [Laughs] I always feel a little crazy around release day. I’m going to try and not be online as much as possible, but I’ll check in. I might do this meditation thing I’ve been doing—this guided meditation my friend sent me, pretty standard-issue. I burned it to cassette, so now I wake up and hit ‘Play’ on my cassette player. And then I might go to the bar tonight.

There’s a cognitive dissonance around releasing a record. There is no way to really wrap your head around the fact that a lot of people might be listening to your music at the same moment for the first time. I got a text message from my friend this morning: “Listening to the new album. It’s so good. But it begs the question: Are you doing OK?” That makes you think about how other people are thinking about you. 

How did you respond to your friend?

I just said yes.

What songs do you think may have caused your friend to worry?

The first half of the record is way more intense. But then the second half gets pretty deep, just in a different way. The whole thing is pretty high-stakes, not a chill listen, necessarily. If I made chill music, poppy or upbeat or something that’s not agonizingly intense, everyone would be like, “Oh, he’s just such a chill guy.” That’s how they would imagine me to be, but it doesn’t really matter what people think about me. 

For this album in particular, I say that it doesn’t have anything to do with me, but really it does. I don’t want to fully remove the role of the songwriter in the songs, you know? I’d like there to be that tension. I want to communicate some kind of growth or progression of thought or feeling. I think it’s unreasonable to assume the songwriter would be totally abstracted from the music—or music like mine, at least.

Why do you say these songs don’t have anything to do with you? I almost feel like I know you through three records. 

In an ideal world, it would just be your music that exists and not the person behind it. You want to remove the personality from it and just have it be a piece of art that exists in its own world, which I struggle to do. I don’t think that’s how my music exists, really. You can hear the author fighting through—the feelings and thoughts coming through the course of my album. I don’t know if I totally care about the story behind songs, but I definitely buy into the cult of the artist behind works of art I love. My favorite artists are like that—Bob Dylan and Townes Van Zandt. It’s impossible to separate them from their music. I don’t know if I believe that that’s good for society or culture. Music should stand on its own, but their music does, too. It’s a mix.

Why is celebrity bad for culture?

We’re at a point in history where I don’t think celebrity contributes to society anymore. What’s the point? The future is more about dismantling those structures, right? I guess putting people on pedestals feels regressive socially, old-world. The opposite would be a band like Fugazi or Unwound who wouldn’t play shows if there was a stage involved. They had to play on the ground. That kind of world is very community-oriented, a model for a very different kind of society. That feels more like something to be admired these days.

Do you feel like celebrity and community are a binary, or that celebrity at least undermines community?

I’m sure there are sociological papers written about stuff like that. On some level, there’s always a hierarchy of popularity, right? Social media forces people onto these pedestals. There’s this weird illusion of celebrity that’s very much central to being online, and that does feel antithetical to community, just being at home on your phone. But whenever you talk to a musician or artist you really love in real life, you have that moment where you break that illusion. You realize that they’re like you a little bit. The more you engage with people in the real world, the less likely there is to be that elevation.

What heroes have you met who made you feel that way? 

Oh, wow. I don’t think I’ve met anyone that I worshiped as a child, where that sense of awe is ingrained in me. And there’s only a couple people where I would really be awestruck. That hasn’t happened yet. I worshiped The White Stripes when I was growing up, so I think if I met Jack White, I’d probably have that moment. I met the photographer Steve Gullick. He has photographed every legend ever in rock history, so it’s like when you meet someone that knew some untouchable person. He’s photographed Nirvana a hundred times, Neil Young, Sparklehorse, Jason Molina. We took some pictures in London the first time I played there. He was so nice, and we’re friends now. But I definitely was in awe, because there’s something about a person who has a very intimate relationship with all these people. He’s like a secondary celebrity, kind of a mythical guy, but also really sweet. 

You’ve said before that writing a song feels so much better than talking about writing a song. I’m sorry to be a sadist here, but what does it feel like to write a song for you?

[Laughs] There’s kind of a spectrum of how certain things make you feel in the process of playing music and being a musician. What’s at the bottom is, like, doing a bad interview. Writing a song is the best feeling. Doing a good interview is in there somewhere. There’s so many other experiences—playing a show, looking at your record for the first time on vinyl. Playing a show is second from top, but finishing a song—well, not finishing, even the process of writing the song—is first. That’s when you feel the best about life, about being alive. You’re just doing your craft, and everything else is just executing it, performing it, packaging it.

That’s why I started writing this album when I did. I was so sick of all the boring shit that you have to do in anticipation of an album. It just went on for so long with my last record—the process of mixing it and remixing it and mastering it. By the end, I just needed to write more music, to remind myself of why I’m doing what I’m doing. I started writing right before Burnover came out just for the sake of feeling good about being a musician again.

Have you always had that feeling, that writing was the best feeling?

I always have had it, but now it’s weird because you immediately think about how other people will hear it. I still do it for the sake of doing it. and I’m pretty good at tuning out overthinking what I’m doing in the moment. But there’s a little bit more compartmentalization now. That’s just part of maturing as an artist. It is like a job in that way, in that there’s all these things you have to work on all the time—psychological and spiritual work, in addition to physical. You just have to know yourself, know what is destructive and productive for you. 

When did you start to think of yourself as a songwriter?

When I learned how to play guitar, maybe 10 or 11, I always wrote songs. There’s people that grow up wanting to be in a band and play rock ’n’ roll, so they might learn how to play guitar and are just doing it because it’s cool. And then there’s people that have no choice. They just do it because they don’t know why they do it, an ingrained thing. That’s how I always was. I never thought about the possibility of being in a band. I never liked playing covers, playing other people’s music. It just always felt natural to write my own songs on guitar. 

It makes sense that my songs exist in some internal world, because that’s how I grew up writing music. Bill Callahan is from right next to where I’m from, and David Lynch partially grew up in Northern Virginia. It’s a terrible place but it makes sense when you think about his work, the obviously horrifying psychological implications about the mundane. Writing music always felt like a refuge, a more interesting internal world, than what was actually going on around me.

And when did you realize that songs were a way to put how you felt about the world at large into music?

I really liked hip-hop early on and then classic rock around when I started playing guitar. But I remember hearing Townes Van Zandt for the first time in a record store in Baltimore. They were playing it on the speakers, and it was one of the few moments I’ve had where it’s not even that you immediately love it but you’re just captivated, like you’ve never heard of anything like that before. It was the CD from the documentary about him, a compilation. Once I heard that, 14 or 15, it changed my trajectory. It’s just very haunting, and he’s barely even trying to sing. It is just so boiled down to its essence.

You’ve told me that part of the appeal of writing lyrics was that it’s something you could control, because you didn’t like your voice. I admire how much you speak like you sing, how it seems like the distance between those two acts is very small. How did you learn to embrace your voice?

Really on my I Looked Out album. I had made music before then, obviously, and put out music online. It took me a long time. I’m slow. Some people are born fully formed artistically, and I feel like it took many years—until I was … 22?—to feel comfortable singing, just singing with my own voice in a way that felt natural. In Chicago, there are all these 20-year-olds who have it figured out aesthetically. Their bands are incredible. I’m just like, “Damn, I was fucking not doing anything when I was 20, just fucking around in a dorm room somewhere.”

You struggled to find a music community where you grew up, and then you went to Burlington, Vt., with a scholarship. Why Burlington?

It was far enough away from home, a freaky little town. It was the right decision, because, as soon as I got there, I was playing music with people. It changed my life—being in a place where you can play shows whenever you want and people are in bands. It was invigorating, and people were supportive, too. I remember doing open mics right when I got there, and people thought it was actually good. That felt like the first time I’d been validated by my peers. It wasn’t intimidating. And it’s a very tight-knit community, everything in a one-mile radius. You can make anything happen in Burlington. If you want to play a show, you can play shows. Your use of free will goes a long way. I had a friend who just ran for sheriff, Chittenden County Sheriff. He didn’t win, but he definitely ran for sheriff. [Laughs] It seems way harder to do that in a big city, kind of impossible in a suburb. 

But Burlington doesn’t look a lot like the rest of the country—it’s much whiter, for one. You’ve been on the move a lot since leaving. Did you feel like you had to go and see the country as it is?

Touring has allowed me to engage with the country in a way that I can’t at home, or when I lived in Burlington. I’ve spent a lot of time in cities, and I lived in New York for six months before college. If I wasn’t touring a lot for the last couple of years, I definitely would have left Burlington a while ago just for the sake of needing to live a richer life, surrounded by different types of people. 

But there’s ways to do that even in a small town. Vermont is slightly more diverse than people think. I would help with farmworker meetings, volunteer meetings, towards the end, trying to engage with the greater community. But I eventually moved to Chicago.

What drew you to Chicago?

It feels very industrious in a genuine way, in a way that doesn’t exist in other cities anymore. It feels very earnest. You go out to a coffee shop, and people are writing. I don’t believe in performative reading or any of that, but people are more invested. There’s less layers of weird performance than there is in New York or LA—everyone just doing what they want to do here, making things for the sake of doing it. There’s a beating heart to Chicago that feels unique. 

By the third time I played here, it felt like a second home. It’s a great place for a writer. You can talk to anyone. You go into any bar and talk to anyone, and they’ll just have a conversation with you. Just being here, I’ve met so many people—not even through music, but through running into a stranger. You end up going to the museum with them a week later. 

Tell me about a time you saw two strangers interact in an unexpected way in Chicago.

I was reading The Heart of the Matter by Graham Greene in a bar a couple days ago. Every time you’re out at the bar in Chicago, it’s where men go to socialize with other men who they don’t know. There’s always some interaction of two complete strangers who have a 10-minute conversation over beers. I was sitting next to this one guy, a 40-year-old tech bro. You know when tech guys try and explain their job and they’ll talk about it for five minutes and you have no idea what their job is still? So there was that guy and then a guy who had been in the military for the last 10 years. They had an interaction, and it felt like the start of a joke.

Speaking of reading, you use “spaniel” as a verb during “Withdrawn.” That’s not a common play, and it instantly told me you were a reader. Where did you find that usage?

[Laughs] I forget. I saw that used as a verb in something, and it had been in my Notes app for a year or two. I’ve been waiting to use it in some song. I like when words make sense without really making sense, the way you understand a meaning without knowing the expression. Since I’ve been writing songs, reading has become essential for finding inspiration, the same way watching movies feels like a big part of “working out” creatively, consuming other forms of art.

You referred to yourself a few minutes back as a “writer” instead of a songwriter, and you’ve done it before in this conversation. How do you perceive what you do?

That’s what I make, songs. If I made poems, I’d be a poet, or if I made stories, I’d be a story writer. You are what you are. Elvis wasn’t a songwriter—no one would say that about him. But we’ll say that Taylor Swift is a songwriter, and what does that even mean? What does any genre title mean? When people ask me what type of music I play, I’m resigned to saying indie rock. I could say rock music. Neither seem true, but both seem true at the same time. 

You’ve mentioned hip-hop as a primary influence on your writing, particularly MF Doom. How does rap shape the way you approach lyrics?

It’s everything. David Berman said something once about how musicians who don’t care about their lyrics are like a painter who doesn’t care about their brushstrokes. That seems true. Hip-hop is the only genre of music where so much thought and intellect go into what you’re saying and how you’re saying it. I think that’s a beautiful, very special way of writing music. There’s so many words in an MF Doom song that you can listen to it 100 times and still be catching the meaning. It asks to be listened to many times, reveals itself slowly. You turn on a lot of pop music now, and there’s just nothing even to reveal. You hear it, and there’s nothing there to change your mind or think about. Hip-hop feels endlessly inspiring in that way that’s so different from most rock music.

This reminds me of “Totaled,” maybe my favorite song on All Set the Bone. It starts off as a tune about a car crash, or what comes after a car crash, about self-doubt and the general anxiety of existence. It changes a little bit every time I hear it. But to be clear, did you crash your car? 

When I was 18, I totaled my first car, which was a ’98 Camry. It was my fault. We were sneaking out of school to go to the mall to get food during lunch. It was snowing, and I was trying to drive, making this hard turn with a yellow light. I went straight into the guard rail. A bunch of my friends went to the hospital, but they were fine. I just walked back to school, because we were close, and took a math test.

But that moment of being in the junkyard, like collecting the shit and CDs out of your completely wrecked car, you don’t really forget that. The real image in my head is: You’re in a junkyard full of cars, and you don’t know who died and if this person was OK or if everyone in this car died or whatever. Something about there not being a distinction between the wreckage left over is haunting. You realize how dangerous what you’re doing every day is, very casually. 

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