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Sammy Tweedy

It's a sunny day and I'm crying as Wilco's "Darkness is Cheap," a track off their new album Cruel Country, plays off a crappy bluetooth speaker on the dining room table that doubles as my desk. There are birds outside fighting at the feeder and the sky is blue after days of rain and the endless gray that defined spring in Chicago this year. Frontman Jeff Tweedy's brittle voice fills gaps between the sparse instrumentation. A horn, a piano, a guitar. It's beautiful and sad the way so many things are nowadays. Before I realize it, tears are rolling down my cheeks.

It's been a long few years. For me, for you, for Jeff Tweedy.

Amid the crushing isolation of the pandemic, divisive politics, and a creeping sense of powerlessness over it all, it was easy to feel lost and alone. As he sings elsewhere on the album, “It’s hard to watch nothing change.” This wasn’t the first time Tweedy has felt adrift and it probably won’t be the last. But it altered him, he says, in a way that feels new. Good, even. “During this period of deprivation,” Tweedy says, “it occurred to me that making music is really everybody trying to figure out how to have more good days than fucking bad days.”

Tweedy knows bad days. The beating heart of stalwart indie band Wilco, he has publicly struggled with addiction and anxiety, depression and debilitating migraines. Migraines so bad that, when he was a boy, he’d vomit dozens of times in a night from the pain, regularly landing in the hospital for dehydration. A vicodin habit to numb the discomfort came later—on tour in 2004, he’d pass out in the bathtub, thinking he might not wake up. Rehab kicked the pills, but the migraines still rage. He had one this morning, pushing our conversation back by hours.

He knows good days, too. “I feel very blessed to have been put in a position to tour around the world and make records and play music for people,” he says. “It’s just a miracle.” Wilco attracts a fan obsession once reserved for groups like the Grateful Dead, leading to a level of success that few indie acts enjoy. The band has performed on every late-night show you’ve heard of and plenty you haven’t. Tweedy sang a song for Li’l Sebastian, the legendary mini horse, on Parks and Recreation, as well as the theme song on a recent episode of Ted Lasso.

the band wilco arrive at the 54th annual grammy awards held at the staples center photo by frank trappercorbis via getty images
Frank Trapper
Wilco, photographed together at the Grammys.

But mostly, Tweedy knows the balance between the good days and bad. How they even out to form a life. “I have felt really, really hopeless at times and I have learned there are really subtle, simple joys around the corner at almost any given moment,” he tells me over the phone—while folding laundry, he admits, sheepishly—from his home in Chicago.

The subtle, simple joys Tweedy has experienced over the last few strange years–years that saw Wilco stop touring for the longest period of the band’s entire existence and resulted in Tweedy home with his family for the longest stretch of his adult life–power our conversation at the end of April. It’s the first interview about the making of Cruel Country, an album Wilco put together in just four months—a blink for the band—and how the simple, stripped-down songs on the record helped save him from the potentially “depressing” experience of revisiting the band’s seminal Yankee Hotel Foxtrot for a series of 20 year anniversary shows this spring. But more than that, it’s a wide-ranging conversation about life, family, legacy and, above all, hope.

Before we get to any of that, Tweedy has a bone to pick with me. A decade ago, I wrote a book satirizing Rahm Emanuel’s run for mayor of Chicago and, through one of those weird occurrences that happen in a big city that feels like a small town like Chicago is, at the release party I got the singer to reenact a scene from the book, where a fictional Jeff Tweedy plays Black Eyed Peas songs at a fundraiser for Emanuel. It turns out, he can’t shake the video from that night. The below has been lightly edited and condensed for clarity.


Jeff Tweedy: I have to say, you were responsible for something that I've had a very, very tough time living down.

Esquire: It's been over a decade!

I'm just gonna tell you a real quick story, I hope you don't mind. Chipotle gave me a free burrito card a long time ago. And whenever I would use it, it just freaked people out that worked at Chipotle because they'd scan it and it would come up as a 100% celebrity discount. I could have bought burritos for everybody in the place, and they'd all be free. I don't know why they sent it to me, and they eventually took it away, but when I had it, nobody would recognize me as a celebrity. I'd be sitting eating, but my name would be on the receipt and there would be people in the back kitchen Googling me, trying to figure out who I was. And one time they came running out as I was finishing eating and they made me come in the kitchen and take pictures with them because they thought I was the guy that wrote “I Gotta Feeling.”

Oh no.

And they were watching the video of me singing it at the Hideout.

That probably directly led to the removal of your free Chipotle card!

It might have. I don't know, but to this day, it’s the closest I've ever come to being viral. I’ve had people criticize me for, like, going out of my way to make fun of that band. I still get requests for that song all the time when I do solo tours. No good deed goes unpunished, I guess.

Well, I'll try to make it up to you with this interview.

No, no, I love it! I was happy to be a part of it. It was such a fucking amazing book and thing to be a part of.

Well, thank you. I tell people now, and they don't believe that it happened.

Well, believe me, there's proof.

There sure is—but that’s enough about the past. You’ve got a new Wilco record coming out, Cruel Country. You picked a hell of a time to make a record about America, man.

Yeah, well, what else is there to think about?

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Was making a record about the problems and promise of this country—albeit in a Wilco way—the intention at the start, or was it more of a thing where as you sat and looked at the whole of it, you realized that’s what you’d done?

A little bit of both. Early on in the pandemic, writing folk songs and country songs—which is something I've done my whole life—really took on a deeper kind of consolation for me. It was like a comfort food to really just focus my writing within those narrower limitations. It’s hard to think of new shapes for a song when the ground is shifting so dramatically, so there were all these country songs and folk songs piling up. Some of them ended up on my solo record, but a whole bunch of them just kept coming.

Wilco had started work on new a record before the pandemic, it was art pop. We had been working toward some new ideas that would be exciting to us. Being a band still putting records out after 20, 30 years, or however long, that’s the fun of it: wanting to make a new shape and surprise yourself. We continued working on some of that stuff during the pandemic from afar, just sending takes around the way all pandemic records were made.

But then when we were finally able to get together, none of that material felt grounded enough for us all to sit in a room and play it together, and so I started breaking out all of these songs that I had actually set aside. I called them Cruel Country from the very beginning. I had a name for the other record too, and we basically made two piles. And once we were able to just sit in the room and play together, this is the stuff that reestablished our connection with each other.

This was the first time in a really long time that you recorded all at once, all together live in the studio. Being in the same space making music, in 2022, feels really profound to me. That must've been really emotional.

Absolutely. Yeah. There was an urgency, a desire, to have a song to sing. A song to sing together. It felt silly to go back to the ways we'd made the last few records, where I did a bulk of shaping of the early basic tracks and people put their parts on as it was being worked out and arranged and it wasn’t all of us playing together in the same room. We basically made pandemic records before the pandemic. But yeah, getting to play music with your friends, it's an intimate thing to do. It relies on wordless communication. All the takes we ended up picking are the ones that just have this thing that you can't really say exactly what it is. They sound like a moment that you want to share with people.

“Finding a song to sing together” is really beautiful to me.

Isn’t it? It's simple. It's elemental. I feel very blessed to have been put in a position to tour around the world and make records and play music for people. I think it's just a miracle. But within that little context of my whole life, there have been little squabbles within communities over authenticity, little squabbles over styles, squabbles over how people go about making their fucking music as if it's something that can be critiqued. But during this period of deprivation, it occurred to me that making music is really everybody trying to figure out how to have more good days than fucking bad days.

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Speaking of what seemed like pretty good days amid a lot of bad days, you spent so much of the pandemic livestreaming with your family. What made you all want to bring people into your lives that closely?

You tuned in?

Yeah, I watched a number of them, especially early on.

Oh man. Well, before the pandemic, Susie was starting to toy around with the idea of live streaming some of the junk—the stuff—in our house and talking about it, but she's a little shy of being in front of the camera and so she thought it'd be fun if we did it together. But then, after the tour got canceled because of the pandemic, it really grew out of her reading all of the comments online from people that were so disappointed. It just really underlined the role the band plays in some people's lives. And I think she just wanted to make sure they were OK, or at least reach out and connect with them somehow. But it grew beyond that pretty quickly.

My own feelings about it was that it was an unbelievable moment in time where there were no stages and there was really a dismantled hierarchy. It was temporary, unfortunately, but for a moment there were no stars, there were no amateurs or pros. We were all looking for that connection that we didn't have any more, and everybody was a little scared. So without even thinking about it all that much before it started, it became a way for ourselves to cope by getting together and learning some songs every night—just so we didn’t go crazy—and to share that experience with other people, to connect to other people. It was a nice thing to do.

Your boys were at home then. Are they both still there?

Yeah, for the most part. Spencer lives with his girlfriend nearby. Sammy was in college when the pandemic started and he’s basically been in his room since.

I'm still reeling from the year and a half that both my kids were home. In many ways it was wonderful and also then I zoom out and think that was insane. Do you feel like you learned something about yourself and your family in that time together?

Oh yeah, I feel changed, absolutely. It's hard—knowing the toll that covid has taken on a lot of people—to express any positivity about it, but for me it created some positive change. I just don't know any other way to put it. I had never spent that amount of time in one place in my adult life, so I had always worried that I wasn't really cut out for that kind of thing. I’d worried that maybe my family had benefited from me being gone and my marriage had benefited from me being gone. Learning that we were actually compatible and able to cope with really challenging time was healthy.

Musically and artistically, I feel like I didn't let that pain go to waste either. I feel like I really reaffirmed that the most basic coping strategy for my whole life is to write and create to lose myself and free myself of a burden. But not just writing songs, learning other people's songs too. We learned like a thousand songs or something over 200 shows at our house. Around seven o'clock every night, Spencer and Sammy would start throwing ideas at me of what songs they wanted to sing. I got better at playing guitar and better at learning how chord progressions work. I mean, stuff I had thought about a lot in my life, that kind of concentrated effort made me better. I feel it now on stage when we play. So all of that, that's all good, but also everything is so terrible.

I think the new record captures that experience of things being both good and terrible. It captures the mournfulness of right now quite well. It has a lot of death in it—just like our lives do—but it also has hope. You describe the record as moving from dark to light and I’m curious how you work to square hope and grief?

I just trust that it happens the way it has always happened through music: that singing about problems—about death, about your fears—doesn't make them go away but it makes them feel less heavy for a little while. And that's good enough, sometimes.

I don’t think you can write a song that's going to make people not care about death anymore, or not care about their own mortality. You can obviously write a song that’s going to bum somebody out all day, but I'm trying not to do that. I think that mostly I just feel a little bit better when I've done something with my imagination that looks at something that is scary to me and I master it with melody just enough to get through those moments. That's working from dark to light, in my opinion.

There’s a line on “Story to Tell,” from the new record, where you sing, “I've been through hell / on my way to hell.” We have been through hell lately, and yet it also sort of feels like we've gone through it just to still be in it.

That’s a quintessential country line to me. You can tell people everything in one line. When I come across a line like that, I feel really lucky. You're always looking for something like that.

For me, I was probably thinking more about the fact that a lot of the things that people claim will send you to hell ultimately kind of put you through hell. But, in a broader sense, yeah, I think life is like that. You do go through terrible times and they pass. You're aware that you survived terrible times and you're stronger than you think you are, but at the same time it makes you aware that there's likely another time like that on the horizon.

I forget who said it, but I often think about a quote I saw once that country music—the good stuff—is really music for people who have lived their life a little. You've been in this band for a long time and you’ve lived a lot of life in that time too. You’re announcing Cruel Country on the heels of the 20 year anniversary of Yankee Hotel Foxtrot, and you’ve been playing all those old songs in their entirety live for the last couple weeks. What is it like to look back on that legacy while simultaneously moving forward?

I think that’s part of the reason that everything's accelerated in terms of getting this record out. Without having this new record we want to share and we want to sing, I think the whole task of recreating Yankee Hotel Foxtrot in its entirety for people would have felt depressing to me.

First of all, none of those songs are songs that we stopped playing, but when they're wedged between songs from other periods in the set, they’re transformed to fit in with our current sound and how we feel. When we play them in a normal set, they no longer recreate the sad landscape that I was walking around in at the time. But these last few weeks when we played them all together and really worked hard at making the arrangements similar to the way we played them in the studio, honestly, it's brutal. I was really surprised at how much it wiped me out the first night we did it. I thought it was powerful and I was really proud of the performance, but I was glad that night that we didn't book 20 shows, you know? I’m not sure if I'm answering the question you asked, but I'm really happy that we have something new to focus on.

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That's part of the reason can't shake some optimism, because I have felt really, really hopeless in my life and I definitely have learned that there are really subtle, simple joys around the corner at almost any given moment. You can't predict them, but they're worth waiting for, and you can have a certain amount of faith that they're going to be there if you're willing to accept them. I hope it doesn't sound new age-y or self-help-y or something, but I think it's just true. Even in my worst moments, the world would unfold into some kind of crazy joyous day and I don't think that's an aberration.