Jeff Tweedy On Allowing Yourself To Fail

WILCO's Jeff Tweedy discusses his latest sonic landscape “Twilight Override”, completing the circuit for listeners and more with KFMH's Bill Klutho on October 14, 2026 in advance of his performance scheduled at Capitol Theatre in downtown Davenport, Iowa on November 7^th.

Bill Klutho: Our guest today is Grammy Award-winning singer, songwriter, producer Jeff Tweedy, also an author and best known, of course, for his work with Wilco and Uncle Tupelo, and his solo work, including his most recent release, “Twilight Override.” Jeff will be in town for one night at the Capitol Theater in Davenport, on the 7th of November. First off, thanks for taking some time to talk with us today. 

Jeff Tweedy: My pleasure.

Twilight Override

Klutho: Twilight Override has been out for a little more than a year now. Is it still everything you thought it would be? 

Tweedy: I don't know how to answer that. I don't know if I look at records as having an agenda. I'm glad it was received well and I'm happy about that. Records to me are something that you put out into the world and they're never fully what they could potentially be because you're lucky enough to have one stick around. They keep finding new people and become a part of other people's lives and that's a beautiful part of getting to do what I do.

Klutho: There was so many different musical options for people to attach themselves to with that album.

Tweedy: Yeah...I mean it's a big record (3CDs) but hopefully a lot of the people that I've talked to like the records…like the whole thing as being an immersive type of experience. The individual songs, hopefully stand up, on their own for lots of people that just hear a song at a time or something like that, but this seems like the unique quality that the record has is what people have responded to. It is almost two hours long, you surrender to just be in somebody else’s sonic landscape.

All In the Family

Klutho: I know your your kids (Spencer, Sammy) were part of the record. John Fogerty is out on tour with his two kids and Willie Nelson has had his kids are playing along with him for years. What’s it like for you to have your children involved in your work? 

Tweedy: It’s better than winning the lottery and a Heisman and a Grammy all rolled into one. It’s just the best thing ever. I think that. Music is really a loving, intimate way to spend time with people. You work hard to make a band feel like family and eventually, a band like Wilco's been around together for so long, we are family. But starting at a very young age, communicating with your kids musically, develops into a language of love and support and it's just great to get to share it but it's something I think we've done since they were little. It’s part of how we interact, how we stay connected and it’s deepened our sense of appreciation for each other. 

Klutho: Not unlike building a pinewood derby car when you were a Cub Scout. (a reference to his book ‘World Within A Song’)

Tweedy: Well, that's great too. I think anybody that shows up for their kids. That's what you're supposed to do. It’s like sitting on the floor and playing and making noise…that’s been our version of playing catch for a long time.

National League Central First Pitch Tour

Klutho: Speaking of playing catch, you've fulfilled a lifelong dream of throwing out the 1st pitch at all the National League Central ballparks. As a former pitcher myself and having thrown out 1st pitches in a couple of minor league parks, I can't imagine what it's like in a big league setting. 

Tweedy: I don't really like seeing myself on a Jumbotron, and don't know if it was a lifelong dream. It's just something I kept getting asked to do. I love baseball so I'd never say no. It just started with the Cubs and then, because I'm from the St. Louis area, the Cardinals got bent out of shape and asked me to come there. And then we played in Milwaukee on a game day and they reached out and so I looked at the schedule and eventually figured out. Then I thought…Well, I'm only two teams away from the full (NL) Central. So I went for it after that. It just seemed like something I should accomplish. It would be amazing to get all of the ballparks but I don't know if there will be the time to get to all different ballparks. 

First Time at Fitzgerald’s

Klutho: You started out this tour with kind of a home field advantage playing three shows at Fitzgerald’s Patio in Cicero, how did those shows go? 

Tweedy: They were great. I've never played there…which is just a weird thing considering all the different opportunities you would think would have arisen and being making the kind of music I've made in my life. But it was long overdue and a really great experience. They’ve newly christened this area as a kind of an outdoor venue too. It was a lovely time.

Klutho: Three nights in a row gives you a chance to play plenty of material. 

Tweedy: Yeah but solo I can play pretty much anything that I've ever written for myself or Mavis or any kind of side project like Uncle Tupelo or Wilco. So, yeah, it's a pretty vast repertoire at this point and I like that aspect of getting to play solo acoustic shows. I don't really have to have a set list and can play anything that pops into my head. Some things I like to play on a night to night basis just because there's certain songs you start to enjoy playing and you want to share them with each audience. But then it gives you an opportunity to make every night kind of unique when you can choose pick from such a big repertoire. 

Set Lists & Playing the Room

Klutho: You have more almost 300 songs now to choose from. I saw a recent interview with David Byrne talking about cycling Psycho Killer out of his set about 5 years ago but that he is putting it back in. How tough is it to put together set list for like the show that you're going to play here? 

Tweedy: Oh, I don't put together a set list. That's what I'm saying...I put out a song list every day. I'll maybe sit in the dressing room and make a list of things I'd like to remember to play included within a bigger list of things that I know I can play at any point. And then refresh my memory on a few things I'm going play along with some new songs usually…if the crowd's good. I like being able to read the room and go with the energy of the audience. 

Klutho: Well, I would think that with your audience, if you would say “I've got a new song”, people are going to perk up a little. We’re always anxious to hear something new from you. 

Tweedy: Oh thanks man. Yeah...that can be a sketchy proposition for a lot of people but I am obviously gonna be attracting mostly people familiar with my music. How deep in the catalog they are is generally different on a night to night basis. And where you’re playing can be very different. You start playing in a room that has a bar that you can see. You may may be better off reminding yourself of songs that are louder!

Klutho: I know some local musicians here that really do play the room. Suddenly, it's loud over there on the left-hand side and then you realize that there's a group of people doing shots. But I don't think that'll be an issue at the Capitol. At least I hope not. 

Tweedy: No, it's just a seated theater, so it's probably fine. 

Stephen Colbert

Klutho: I know you were a frequent guest of Stephen Colbert. Did you smile a little when the show received those Emmy awards earlier this year? 

Tweedy: Yeah it's so well deserved. I’ve gotten to be fairly good friends with Stephen over the years because we played quite a few times on the Colbert Report...I bet more than almost any other musical act for that show. And for almost every record since then… I've made an appearance on the show. And for my books, I've actually sat in the chair and done interviews and stuff, so, we've kind gotten to be pals and, I have to say, Steven's one of the best people I've ever met. It’s really kind of unbelievable that he would become something controversial because he's a genuinely decent person.

Klutho: You were one of his guests in the weeks leading up to the final episode. You could see a real connection between you two. 

Tweedy: My wife and I went to the shows’ finale party and have kept in touch. We were supposed to see each other at an outdoor show we were doing this summer in South Carolina but it got rained out which was a bummer, He's obviously a very vocal critic of somethings that affects us all. But honestly, that just grows out of his decency. I think there’s a lack of decency and the way our politics have been taking a turn in this country for some sort of cruelty. It’s a sad sad turn of events where greed and other people's misery is somehow okay. 

Klutho: You always hope that things are going to get better and I think they will. 

Tweedy: Well, nothing stays the same and that goes for times like these also.

Beatles Anthology & Woody Guthrie's Love Notes To the Future 

Klutho: Elvis Costello just released an expanded edition of ‘My Aim Is True’. You’ve had some experience with expanded editions of your albums…you won a Grammy for ‘Ode to Joy’ back in 2021. In the book about your 50 most influential songs, you couldn’t tack down The Beatles for just one song but you mentioned the Beatles anthology and how it was eye-opening for you. To know that these songs didn't just burst perfectly onto vinyl…that there was a process. Is that kind of the way you look at doing special editions? 

Tweedy: Well, I don't know many people that can compare themselves to The Beatles. I don't know how many people are looking forward to 12 different versions of one song. But there are enough people that are interested. There is something unique about the way Wilco has recorded a lot of the albums that have been expanded. People have formed an opinion that includes themselves in the record. When a record becomes a part of someone's life, it is nice to let them in a little bit…into a deeper sense of how it was made.  But for The Beatles, for me when I was a kid, that was like being given the secret formula to the Colonel's chicken or something. I think it was just enough insight to be able to reverse engineer a lot of how the studio works and how creative minds inside of a recording context approach things. It makes it a lot more visible what you can do and why it ended up the way it is. 

Klutho: Speaking of expanded editions, there's a complete 4CD set of the Mermaid Avenue albums coming out in early December. (Mermaid Avenue project is a landmark modern Americana collaboration where Billy Bragg and Wilco set previously unheard, unrecorded lyrics by Woody Guthrie to newly composed music)

Tweedy: Those sessions have taken on a life of their own. It’s really flattering when anything you've been a part of sticks around, finds new people and ends up crossing over into a new generation. It's kind of what it's for. It's one of the reasons you document it and make records. It's kind of a love note to the future and you get to witness it. It is really wonderful. And of course, there's an added layer of speaking across generations because it's Woody's (Guthrie) words. So, it's almost a 100 years of communication. 

Klutho: I found it amazing that he had written so much and that there was all that material available for you to work with. 

Tweedy: What we ended up using is just to drop in the bucket. There are 100s and 100s of manuscripts and lyrics and things typed on the back of his children's drawings and other places. 

Learning More From Failure

Klutho: And you took them and ran with them. Speaking of the songwriting process…a couple of things. Are there songs where you thought ‘that's exactly what I wanted to say’ or songs that you look back on now and say ‘what was I thinking’? 

Tweedy: I tend to be pretty forgiving of myself.  I mean it's nice to see growth. It's nice to know that I wouldn't write a song like Screen Door now. Or at least I would make certain different choices in a different way, but I still think that, at its core, it’s the same impulse. And it's nice to see it being a constant. I just want a new song to sing and that's kind the way it’s always been. Once I've got a new song it becomes something for somebody else to know. I do believe there's a certain amount of ownership in each individual person's relationship with the song. Their consciousness is putting it together. They're the ones making the images in their heads of what it is that you're saying. They can misread it completely and still have a profound connection to it. So I feel compelled to honor that. And so there's hardly any songs, if I get asked to play it. I honor it. I think that for myself. I wouldn't walk around thinking I really want to play ‘Jesus, Etc.’ for myself. 

I've played that song a lot. But I never feel like I'm playing it too much when an audience sings along with it and I get to complete that circuit for an audience. And you get the sense that it just feels worthwhile. 

Klutho: What is your songwriting process? I've read you have notebooks filled with lines on them and you use that in the process. How do you how do you go about writing a song? Actually, you've written a book about it, so maybe people could read that. 

Tweedy: I don’t know if I can describe it. Once you write a book about something… a single question in an interview, kind of can't compete. (Klutho Note: Check out Jeff's book "How To Write One Song: Loving the Things We Create and How They Love Us Back”)

There's a lot of different parts of a process for writing a song…there’s no one process. But the main thing, if you're going to answer a question like that concisely, the main thing is to just start. Develop some sort of a routine or habit of writing, and most things will grow out of having that discipline or that practice, a daily practice. And allowing yourself to fail…you learn more from failure. You don't learn from your perceived successes, you don't like write a song and say ‘Oh, that's the greatest song I've ever written…I guess I write great songs.’ That's not going to teach you anything.

New Material & Collaborations Always In the Works

Klutho: Speaking of new material, anything in the works?

Tweedy: Well, yeah, always, 

Klutho: That's why that's you have The Loft. (Wilco’s Chicago base that includes a studio)

Tweedy: I have the Loft. It’s not really an exaggeration to say that I write a song every day. I call a lot of things songs that maybe wouldn’t be a song to somebody else. But I can hear the potential in and document them on a daily basis. I end up with a lot of finished, fully-formed songs laying around. I don't know what's going to happen to all of them. But I know there are a lot of them. 

Klutho: So any more collaborations? Like you and Mavis (Staples). Any more collaborative efforts with anyone? 

Tweedy: Yeah, there's some stuff on the horizon but not stuff I'm probably willing to talk about yet or shouldn’t. But I like playing with other people, and I like being given the opportunity to learn from other musicians and. I like playing music and all of the opportunities you get to do it. You learn something and you grow. That’s the best part of it, you know? I like feeling like I'm getting better or like at least I’m still learning things. I like feeling like, not dismissive of my past, being able to measure myself against my abilities just even on the guitar. Honestly, the guitar is like my real barometer. I play guitar a lot and knowing I can play things. If something's easier for me than it was five years ago, it is really just a wonderful feeling. I think everybody should have something they work at like that, that gives them a little bit of a marker of accomplishment. 

John Prine's 80^th Birthday Party & Columbia House

Klutho: So, how was it playing at the John Prine 80th birthday celebration? 

Tweedy: Oh, it was great. I mean, those kinds of shows can be a little bit nerve-wracking because it's like a talent show. There’s sort of an unnatural flow to a show like that where each song has an individual performer that comes out and sets out a different microphone and the flow of the show is in fits and starts. So I was 2nd to last before the big encore, so it’s a lot of waiting around and anxious to play. 

Klutho: I don't know if you read that Columbia House shut down in September. In your book’World With A Song’, you said you were in the process of filling out the ’13 albums for a penny’ form and your brother told you to stop, went to his room and came back with a boatload of albums that changed your life. I didn't know whether you had seen that news but Columbia House has finally said goodbye. 

Tweedy: It’s hard to believe they stuck around that long, to be honest. That's the shocking part of that bit of news to me, like what would they possibly be doing, once you reach the digital age and streaming. But I can see why they shut down…the government should have shut them down a long time ago because it's predatory. Yeah, I feel like I dodged a bullet. I’d probably still owe them money! 

Klutho: And it wouldn't be right if you sounded Billy Joel. 

Tweedy: Yeah, well, my brother actually had Billy Joel records, so I didn't dodge that bullet.

Klutho: Jeff Tweedy…thank you for your time. Jeff will be at the Capitol Theater in Davenport on November 7th his last show at the end of a small tour for you. Wilco will be on stage back in Chicago in early December but we're really anxious to see you here the 1st Saturday in November. 

Tweedy: Looking forward to it. Thanks for talking to me.

Learn more at https://jefftweedy.com and https://www.firstfleetconcerts.com/events/detail/jeff-tweedy-solo-1480580

Listen to Bill Klutho on www.99pluskfmh.com Monday through Friday from 9am to 1pm as he curates blues, rock, jazz and reggae classics and new music alike.

From the archives comes Reader publisher Todd McGreevy's concert review of WILCO's November 2002 live show at the Iowa Memorial Union in Iowa City, Iowa: https://www.rcreader.com/music/more-alt-country Excerpt: “Not having cultivated an appetite yet for Wilco’s sound, which has been rightfully called a new American aesthetic, I found myself wincing at moments of formulaic pop and nearly trite country-fication. But with each song, Wilco turned those clichés on their ears and surprised me with complex rhythm and lead-guitar arrangements, fierce soloing by Tweedy, wistful and haunting keyboards, and consistently inventive drumming.”