10 minutes with... Jason Isbell

By Anastasia Stanmeyer

July 2026

Read Berkshire Magazine's July 2026 Issue.

The Last Honest Songwriter

A conversation with Jason Isbell is one of self-reflection. Honesty and vulnerability are key to what makes him one of the best contemporary songwriters in Americana music. Despite all of his success, Isbell continues to “do the work” in his songwriting, digging deeper into themes that address addiction recovery, the human condition, and his Alabama roots. The six-time Grammy® winner is known both for his solo work and his band, the 400 Unit, with such acclaimed albums as Something More Than Free (2015), The Nashville Sound (2017), and Weathervanes (2023). On screen, Isbell made his major film acting debut in the 2023 film Killers of the Flower Moon, working alongside Leonardo DiCaprio and Robert De Niro. He then toured the world with his band, including a stop at MASS MoCA’s Solid Sound Festival. Isbell slowed down his pace and released Foxes in the Snow (2025), his tenth studio album featuring only his voice and guitar. He is back on tour with the 400 Unit and will make his debut performance at Tanglewood on Tuesday, July 28, with special guest Patty Griffin. During a recent interview, Isbell talked with me about being vulnerable, songwriting, acting, and Pokémon.

What can the audience expect when you perform at Tanglewood?

We’re sort of between records. I put out a solo record last year, and we haven’t put out a full band record in a while. So I’ve taken this opportunity to make the setlist out of the entirety of my career.

Well, anything you sing is going to be great.

Well, that is patently untrue, but thank you for saying that. There’s so many bad songs before you get a good one, even if you do it all the time. I’ll start them and leave them, or I’ll take little pieces and move them around, but nobody is just writing only good songs. The trick is to stay out of your way—don’t edit while you write. There are people who finish songs that are actually bad, and I like to do that every once in a while just to see what went wrong.

Tanglewood is the Boston Symphony Orchestra’s summer home. Does performing in that environment influence how you’re going to approach a show?

I approach every show pretty much the same way, which is just to go out and try to be in the moment. Sometimes things that take you out of the moment happen while you’re performing, and then you have to work really hard to get back in it and stay in it. The best venues and the best audiences are the ones that give you what seems like cohesive feedback in real time. So, if you’re playing a really loud song and the energy coming off the stage is really high, and the energy from the audience is also really high, then that allows you to stay right where you are. But if for some reason that’s not happening, you have to remind yourself to be in the moment and be participating in the thing that you’re doing rather than judging how it appears. That’s tough sometimes, but that’s just part of being a pro. Also, I understand that there are different reasons for the audience to be subdued. Sometimes, they’re just listening really, really closely. For my crowd, that’s a thing that happens more often than not. When the audience is seated and they’re quiet and they’re not very excitable, it means that they’re paying really close attention. But sometimes on stage, I have to remind myself that this doesn’t mean you’re putting people to sleep.

Is there a connection between Americana music and songwriting, and classical compositions in terms of structure, storytelling, or emotion?

All music is connected by the circle of fifths and by the overtone series. We didn’t invent these rules but discovered them. It is just naturally the way tension and release operates in nature. So, there’s going to be a lot of things in common. But we are dumb. The people who write pop songs, Americana music, rock-and-roll music, or country music, we are just barely touching the surface of what a true composer has to know. And for good reason, because if we get too far into it, then it’s not rock and roll anymore, and it bores the hell out of everybody. That’s not what you want. If you’re listening to carefully constructed orchestral music, then it should be well put together in a way where you don’t break any of the rules, or if you break them, you do it with intention in a way that shows that you know what the rule is before you break it. For us, we’re just up there pounding on guitars and drums and singing essentially one of the same 20 melodies over and over, throughout decades. What really is our stock and trade more than the theoretical understanding of music is an attempt to understand the heart and translate it into language. That’s something, unless you’re talking opera, that a lot of the more trained musical genres don’t even touch. They can get the same effect; they can get to the same place as we can. It’s just that we have to use words to do it, because we don’t know all that many chords.

Your last album, Foxes in the Snow, is a stripped-down recording—just your voice and the Martin guitar. What drew you to that level of simplicity at this moment in your career?

Well, I hadn’t done it before, so that made it very appealing. And it was one of those things where I could be different as it compares to the rest of the music that I’ve made, but not weird for the sake of being weird. I didn’t have to look very far to find something new. And that’s always appealing to me, because if you put too much weight on making something that is different from what you last made, then you won’t have your priorities in order. Our top priority is to connect with people on a very specific level. I still wanted to do that, but I also wanted a record that didn’t sound like my catalog. Then, you know, I’ve been through a lot of personal changes in the time leading up to the making of Foxes in the Snow, so I wanted to document that in a way that seemed cohesive with my personal life.

It’s been described by critics as re-centering you, the artist. Did making this record seem to be a reset or a risk?

That’s a good question. I think I’m trying to create risk creatively. So it did feel like a bit of a risk, and I wanted it to feel a little scary. A lot of people, I think, lose the spark. You get older, and you don’t have so many things to hide from. Early on in your life, when you’re writing songs or making any kind of art, part of the reason that you spend so much time in that chair is because you’re hiding from everything outside of the room. Not always; some people have a very uncomplicated childhood and all that, but most of the folks I know start out writing songs or painting or playing a guitar or whatever it is they’re doing to get away from the rest of the world. The rest of the world will sometimes give you privacy and a little bit of safety if you can convince them that you’re doing something worthwhile on the other side of the door. When you get older, everything is nice. My house is nice, and the people that I spend my time with are wonderful. It takes more to put me in the chair and keep me in the chair, and so the easy out is to write broadly and vaguely, not plumb the depths of your psyche or your emotional life as much as you might have when you were younger. You have less to prove if you’ve had some success. So, you have to find ways to scare yourself and take those risks. I wanted this album to be something that was very immediate and visceral. I wasn’t trying to impress anybody with how much I know with these songs; I just wanted to take the story from point A to point B. The scary part was not knowing if I would live up to my own expectations. I’ve had enough positive responses from exterior sources, and I know now that I’m not full of shit. I can write songs. My own standards keep me honest.

What’s your next risk?

Sometimes, it’s very easy to find the challenge—like the concept of writing a song with the world in the state that it’s in, with so many people disconnected from their community and isolated and inundated with bad news. Those are the people who are privileged enough to only have to deal with the news, not the reality of the news. It’s hard to hold the concept of creating in my mind long enough to create and then to find out, what am I going to write about? What am I going to talk about? But I’ve always leaned on the craft of it, the idea that there is this rhythm of implicit reference. You can use allegory in small ways or big ways and write about anything that you need to write about without that being the immediate narrative of the story. I’ve been writing songs lately, some of them that are kind of nail on the head: This is what’s upsetting to me right now. And some of them are very far away and very allegorical. There are pieces of that inside those songs. I think there’s going to be plenty of risk and plenty of challenge. Things are getting harder, I think, for everybody—almost everybody, all the good people, anyway.

When you said that it’s hard to concentrate, I understand what you mean.

It’s tough. Why would I sit here and write a song with all this going on? It’s either get out in the street and start throwing Molotov cocktails or just curl up in a ball and wait until it’s over. Those seem like the only two rational options, but we have to find something in-between. And art is important. It’s always so important, because it’s not necessary. It’s decorative. Nobody’s eating these songs and using them for shelter. It reminds us of what’s different from us and the animals, and right now, that’s the thing that we need to be reminded of.

And this is one of those times when songwriting is most important?

Yeah, maybe so. But I recoil at the pressure that is put on creative people. “We need a protest song.” It’s like, you have a lot of protest songs. What you need to do is listen to them and actually pay attention to them. And every song is a protest song. Every little piece of art, to me, means that somebody had a big enough pile of food in the cave where they could take a minute and decorate the place instead of just drawing, well, this is where the bears are, and this is where the food is. They can go, well, I’ve got enough food for once. So maybe I’ll just draw a picture of my kids or something. It’s amazing to think. We went through thousands of generations before somebody got five minutes free. And that’s when it was born. So, to me, I feel like that’s always a protest against all the forces that are trying to keep us either busy or dead.

Has this latest solo album altered the way you think about arranging or storytelling in a live show? Is there anything that’s changed in you after you produced the album and then went back to your band, the 400 Unit?

It alleviated some of my concerns about pacing, because I played a lot of solo shows behind this album, and I realized that the songs, if they’re strong enough, they’ll do the work of pacing for you. That’s not to say that I’m going to play five slow songs in a row, but you might see three nowadays. I went through so many years of thinking we’ve got to keep everybody on their toes. We’ve got to have a slow song; we’ve got to have a fast song. And then I go out and I play these quiet, small songs—everything becomes small in the solo situation—and it worked so well that when I went back with the band, it kind of made me think, okay, we don’t have to punch them in the face every other song to keep them interested.I did miss the horsepower when I was doing the solo record and playing the solo shows. It’s walking to work rather than driving. It’s nice for a lot of reasons, but you also miss that acceleration.

When you’re writing, are you thinking about the audience, or is it more of an inward process?

I have one sort of educated stranger because you can’t get self-referential in these songs. So I have a representative of the audience that I’ve built in my head. Just in the writing process, the audience is a stand-in for clarity, because something has to hold you accountable or else you’ll get vague in ways that you don’t mean to, and you’ll get self-referential. That happens a lot in songs. For example, when somebody is hosting SNL or something, and the joke is only funny because of who said it, I try to avoid that. So I do need to have a representative in mind when I’m writing new songs.

You’ve written everything from relationships to addiction to the complexity of Southern identity. What are some of the themes that feel most urgent right now or compelling to you?

It’s the fragility of all of us—humanity in general, but on a personal level, too. The fact that you become stronger the more vulnerable you’re willing to be. The more you participate in community, the more it gives you the opportunity to develop as an individual. These are things that I think are really important right now. It’s kind of a perfect storm of separation. I don’t mean division, because that has a different connotation. I think we should be divided. I think it’s very important that we are divided, because everybody is against war until somebody makes them a slave. I think division holds that same sort of connotation of well, we should all just agree to get along, but if we do, a large portion of us is going to be left out of the process of decision-making in a really bad way.

What I’m more interested in is experiencing your community and understanding more closely what your neighbors are like and revealing yourself to them. Understanding that it’s okay to show weakness is still a major problem. Actually, it’s getting less cool to show weakness and vulnerability, because the people in charge are so incredibly weak and vulnerable, and they know it, and so they’re doing everything they can to keep from showing that. Making these impulsive decisions with these horrifying consequences just because they won’t say, “I don’t know exactly what to do here. I’m going to take my time and try to figure it out.” And then there are so many commercial capitalist motivations for us to be separate. You and I would have been sitting in a room having this conversation 50 years ago. We’ve sort of reached a perfect storm of separating us all from each other, and it’s a lot easier to form biased notions about the other members of your community if you aren’t looking them in the eye.

Has your songwriting evolved through the years by what’s around you?

Thematically. Unless you’re Dylan, who did just the opposite like he does everything else, you start off writing about yourself and your heart and these personal relationships. You get a little bit older, and you’re like, well, that feels kind of naïve and immature. So you start writing about the world outside, and it’s very easy in that transition to lose the magic and to go from being very specific and emotional and vulnerable in these songs to being set in your ways and closed off and vague. There’s a real narrow line between immature and vulnerable, and we need to make sure that that stays in place, because the narrator needs to grow in order for him to be more believable and to sell the story that he’s telling. At the same time, you can’t outgrow your willingness to be humiliated, because if you do that, then you close yourself off and you start writing these big, terrible—and I’m talking about terrible—songs about the world outside. It’s amazing how great somebody can be at writing songs when they’re in their 20s, and then they have some success and start writing literally the worst trash songs you’ve ever heard. The primary reason for that is this combination of their life getting better and them also being afraid to continue to dig for what’s inside of them because of the embarrassment of it. So, I try to continue to embarrass myself in these songs and say things that aren’t comfortable. A very important rule for me is that if something makes me uncomfortable, it has to find its way to stay in the song.

You’ve been doing this for a long time, so it’s probably a bit quicker for you to write songs, isn’t it?

It’s quicker to get one line and then slower to get one song. (Laughs) Like I said earlier, it’s harder to stay in the chair. I’ve got a kid, and I can afford groceries and all that stuff. So it’s tempting to take the kid to the grocery store. But to get one line, it is much quicker.

You’ve done some acting. Are there any other on-screen projects on the horizon?

I’ve been working on a couple of small parts here and there. I don’t think that would ever become my primary job, just because I really still love playing and touring and writing songs more than anything else. But I like helping people tell a story, and I like to see the way a director creates the environment. I think that’s really helpful to me as a songwriter, because it’s all about which details you choose to bring in, and then you let the viewer’s brain fill everything else.

Is there anything we should lookout for?

I did a movie with RZA from the Wu-Tang Clan, but I only was there for a few scenes. He and I wrote a song together for that, which was really fun. It was more like one of my songs than one of his. He sent me a demo on his phone of him playing the guitar and singing a folk song, which was amazing. This dude is so talented. He can do pretty much anything on earth. The movie is called One Spoonful of Chocolate.

How has success changed you?

It’s really hard to know what has changed me. Thank God I’ve been changed, but I don’t know what did it. I know having a kid did it. Creative success certainly did it. Critical financial success, commercial success, that all changed me in some ways, too, because my day-to-day life is very different today than it used to be. I got up, got my daughter ready for school, and then I took a nap. Then I’ve just played guitar all day, so I don’t know if that’s changed. Minus sending my daughter to school, that’s what I would have done when I was 14. Success has given me an opportunity to spend my time the way I want, and I’m eternally grateful for that. If I want to be somewhere, I can go there and be with the people that I care about. Possibly it’s made me a little bit more skeptical of new people and of the world at large. It’s also made me more confident with the work that I do, which can be a really good thing, as long as it doesn’t lead to complacency. But also, time will change you in those very same ways.

You sound very wise for your age, because you’re not that old.

Well, thank you. I’m 47. My teeth are much younger, but the rest of me is 47. I’ve been around a whole lot of different kinds of people, and I’ve moved through very different stages and different circles and bounced on the bottom a few times and gotten myself into some pretty rough situations, and then wound up in a place that I’m very satisfied with and very proud of. Hopefully, through all of that, I learned a little bit of something, but, ultimately, figuring out that I don’t have a whole lot of answers and being okay with that has done me a lot of good. Right now, I’m in the process of trying to figure out which questions to ask.

How old is your daughter?

She’s ten and a big Pokéman fan. Today’s argument was over whether or not she should take her Pokémon cards to school, because she really wants to show them to her friends, maybe do a little trading. But this makes me nervous, because, you know, when I was a kid, you take something to school and there’s like a 50/50 chance that’s going to get stolen. So

I have to remind myself, first of all, that her school is not the same as my school. Also, that sometimes you just have to let them learn. Last week, we went to a Pokémon trading night at this little card shop about an hour away from home, and there were 80 people in there trading Pokémon cards, ages four to 50. It was serious business. And why not? The art on the cards is gorgeous, and it’s social, and it teaches you how to negotiate with people and how to value certain things. I’m into it. I’m gonna have to take her to Japan sometime soon.