JEFF TWEEDY THINKS THE ENDING IS ALL WRONG. The singer and songwriter for the band Wilco leans forward on a black leather sofa, set before a large recording-studio console, in the group’s cavernous northwest Chicago loft. The space, stacked to the ceiling with vintage amps, drums, and guitars, doubles as the band’s studio and rehearsal space, and it’s the closest thing to an office that Tweedy, who began releasing records with his first band, Uncle Tupelo, in 1990, has ever known. “I still kind of regret one edit at the end where we made the solo longer,” he tells Tom Schick, the in-house engineer. “Now I wish we would have ended it after two rounds—how it used to go.”

Schick, on a stool nearby, sifts through old rough mixes on a computer and cues up the part. Whenever Tweedy—who, at 51, has let his gray hair grow to his shoulders and increasingly resembles an adjunct community-college humanities professor—listens to a song he’s written, he sits on the sofa’s far left side, near the window. He then rests his head back and crosses his right foot over his left knee, as though he’s mulling a problem but also maybe trying to doze off.

At this moment, however, Tweedy isn’t listening to a song but to the intro and credits of an audiobook—his audiobook, of his new memoir, Let’s Go (So We Can Get Back), out in November—so he’s sitting upright. His attire today: an El Paso Chihuahuas baseball hat, dark jeans, an olive jacket, thick-rimmed glasses. He spent three and a half days last week recording the audiobook here at the loft, before finishing up some bits this morning. He laughed when his voice first came through the speakers, reading the book’s title. But he’s not laughing now. There’s something amiss with the fuzzy rock backing track that plays beneath the credits. Though Schick has already sent the finished audio to the project director, Tweedy wants to change and resend the track anyway, and understandably so.

The memoir marks a significant moment in his career. Over the past 20 years, few other contemporary recording artists have explored their inner life as adeptly as he has, first with Uncle Tupelo and then with Wilco, which he formed in 1994 and which will begin work on its 11th studio album in January 2019. The group endures as the Big Important American Rock Band, at a time when rock music feels neither particularly big nor particularly important, and does so largely because of Tweedy. He writes earnest, country-tinged pop music, with lyrics that are as opaque as they are beautiful, such as when he observes that “our love is all of God’s money” or suggests “Let’s forget about the tongue-tied lightning / Let’s undress just like cross-eyed strangers.”

Fittingly, the novelist and short-story writer George Saunders recently called Tweedy “our great, wry, American consolation poet,” and R.E.M.’s Peter Buck has said he’s “one of the best songwriters of his generation.” If nothing else, he has a freakish ability to coax emotion from grown-ass men. Nick Offerman played Ron Swanson on NBC’s Parks and Recreation and is a friend of Tweedy’s. The first time he heard Wilco’s Being There, “I stared at my reflection in a slow-moving creek and wept,” he recalls. “I was like, Holy cow—this is everything.”

Though Tweedy’s lyrics tend to be oblique, his new memoir is anything but. It affords an intimate look into his childhood, family life, music career, and creative process, and includes details he has never before divulged about his opioid addiction, subsequent rehab stint, and other struggles. “I’m trying to be open and honest about the things that I think we would all be better off if everybody was open and honest about,” he tells me. He reveals, for instance, that a 25-year-old female record-store clerk sexually assaulted him when he was 14, an encounter that plagued him with guilt. “It would have been really great to have a get-out-of-jail-free card so that I could’ve said to my mom, ‘I think something that happened was really wrong.’ ”

The book isn’t without laughs, though. It includes stories about Tweedy growing up in dead-end Belleville, Illinois, outside St. Louis, as a son of a railroad man; goofing around with Jay Farrar, his partner in Uncle Tupelo, and now of Son Volt, with whom he had a notorious falling out; and meeting and falling in love with Susie Miller, his wife and the mother of their two college-age sons, Spencer and Sammy.

“I’m trying to be open and honest about the things that I think we would all be better off if everybody was open and honest about.”

Adding to the memoir’s significance, it coincides with the release of Tweedy’s first solo album of original material (assuming you don’t count, and you shouldn’t, a soundtrack he did for an Ethan Hawke movie, in 2002, or the 2014 album Sukierae that he recorded with his oldest son, Spencer, and released under the moniker Tweedy). On the album, titled Warm, like in the memoir, Tweedy grants a candid glimpse into his life and mind, so much so that playing the songs live has given him a rush. “It’s like, Holy shit, I’m exposed here,” he says. “Some part of me that would like to protect itself is in danger.”

In the control room, after the end credit is fixed, the discussion turns to Tweedy’s name and how to use it in a press release announcing Warm. Tweedy asks the band’s publicist, who’s working on a laptop across the loft, how she’d typically refer to an artist in a press release. She’d go by the last name after the first mention, she says. But they’re trying to make clear that this is a Jeff Tweedy project, not a Tweedy the band project. Tweedy shrugs, not really having an answer. Then he adds, “Jeff Tweedy is just trying to be the best Jeff Tweedy that Jeff Tweedy can possibly be.”

THERE’S AN 800-POUND gorilla in the room, standing on its hind legs. Or at least it would weigh 800 pounds if it were real and not some kind of horror-house prop. Either way, it’s huge and is wearing a bright green T-shirt bearing the number 51. Colored balloons dangle from a shelf behind where Tweedy and I sit at a table in the loft kitchen; nearby, a photo of Dave Grohl, doctored up to resemble Jesus, hangs on the wall. “It had a 50 on it last year for my birthday,” Tweedy says of the gorilla. “Then I showed up on my birthday” a few weeks ago “and he had a different shirt on.”

Given Tweedy’s age, Let’s Go is on the early side as far as rock-star memoirs go: Bob Dylan, Keith Richards, Patti Smith, and Bruce Springsteen all hit at least 60 before publishing theirs. “I wasn’t sure somebody would still be interested in me writing a book in 10 years,” Tweedy says, maybe joking, maybe not. Plus, “Spencer convinced me that some aspects of my recovery could be helpful to someone,” he adds. “That was a good enough reason to try and write it.”

The memoir, premature or not, does signify a perhaps fraught moment in Tweedy’s career. “I feel like the book is a dividing point between feeling like I’m the oldest young person to feeling like the youngest old person,” he says. Rock & roll was built and survives, however limply, on youth culture, so at his age “you start to feel a little bit more other than what’s happening.”

For a decade or so, however, Tweedy’s music was very much what was happening. Wilco’s first two albums, in 1995 and 1996, belonged to their era: country-inflected rock when rock was having a moment. Then came the sugary, substantive pop of 1999’s Summerteeth, followed in 2002 by the masterful Yankee Hotel Foxtrot.

With Yankee, Tweedy pulled apart and rethreaded American music, incorporating experimental textures with traditional song structures, for an effect The New Yorker called “brilliant, battered.” The album was originally slated for release on September 11, 2001, and Tweedy’s lyrics, listeners quickly noticed, were spookily prescient, with references to American flags turning to ash, tall buildings shaking and scraping together, and voices singing sad songs. The album remains the band’s most critically acclaimed and commercially successful release, and it elevated Tweedy to the status of Major-League Rock Songwriter. “A lot of things he addresses in his songs are timeless,” says Jim O’Rourke, a former member of Sonic Youth, who mixed Yankee. “You don’t get everything in one listen, but it’s still accessible enough for anybody to hear it and know, OK, this is something I can revisit; this is something I need to think about.”

Whereas Yankee had its moments of levity—listening to heavy-metal bands play by the river, proclamations and assurances of love—its 2004 follow-up, A Ghost Is Born, starts with someone crying on a bed and ends with 12 minutes of grating drone and a song about how the greatest artists die unrecognized. It’s pretty bleak, and pretty excellent; it earned Wilco a Grammy.

Since then, the band’s releases have been generally well received but haven’t resonated as its previous records had. In recent years, music websites like Pitchfork have derided the band as “dad rock.” And, sure, most of Wilco’s six members are indeed fathers, and Sky Blue Sky is basically Wilco does Crazy Horse. But the diss has strong whiffs of ageism particular to this era, like Mark Zuckerberg’s quip that “young people are smarter,” and speaks more to perceived hipness than to musical merit.

Still, at the kitchen table, Tweedy does concede that popular culture has moved away from guitar-forward rock music, on which he built his career. He has no desire to save rock & roll, he says, fearing that trying to would turn the genre into an academic pursuit, like jazz or poetry. He draws inspiration from the past but says, “I don’t feel good about it unless I feel like I’ve used that vocabulary to say something that’s new to me, or that I’m bringing something to it.”

Because of this, he has subverted expectations, delivering knotty—and not entirely satisfying—albums, such as 2015’s Star Wars, that, to the disappointment of some fans and critics, only casually resemble Wilco’s early work. But with these releases, the band has remained energetic and vital—long after most groups of its vintage have morphed into nostalgia acts. Besides, Tweedy can’t stand to feel stagnant, to create the same thing twice. In fact, he loathes it; it makes him uncomfortable. Though he knows that you might want him to make Yankee Part Deux, he can’t; he wouldn’t feel right about it. To mimic or coast on past achievements means you’re not paying attention to the world, he says. And he wants to remain fully aware. So he keeps exploring new sounds, and Wilco’s lasting relevance owes, in part, to his prolific output as he does.

“It’s just album, album, album,” says Fred Armisen, of Portlandia and Forever, and the bandleader for Late Night With Seth Meyers. “He’s playing basically with the same musicians, and I think if you keep going like that, people gravitate toward you.”

As we talk, Tweedy mentions the podcast You Must Remember This, which specializes in debauched tales of old Hollywood, and our conversation soon moves to drugs, as do most interviews with Tweedy, somehow, one way or another. It bothers him that rock & roll has long glamorized narcotics, and his memoir undermines any allure of substance abuse. In it, we learn that, as an addict, he stole morphine from his ailing mother-in-law; scored Vicodin from a Wilco fan who worked at a Walgreens; and, in 2001, fired Wilco guitarist Jay Bennett, who also had a pill problem and was a negative influence, fearing that he might die if he didn’t. “I’m sure a lot of people have been hurt or killed following the example of people in my profession,” Tweedy tells me, unmoving in his chair. Bennett, who died of an overdose in 2009, is perhaps among them. If musicians were singing about and exalting any other product that claimed lives, Tweedy continues, “people would start to be pretty fucking angry about it.”

Tweedy, for his part, bought into the druggy rocker cliché enough to believe that he didn’t conform to it, because his addiction was “more stage-managed or something.” He developed a Vicodin habit while recording Yankee Hotel Fox, as a way to temper the chronic migraines he’s had since childhood. But by the time Wilco convened in New York City, in the winter of 2003, to record A Ghost Is Born, he’d degenerated from a pill fiend to an honest-to-God drug addict, and accepted that he was going to die before the sessions ended. There were no all-night parties or hot babes or bottles of Jack—just Tweedy alone in his room at the Flatotel hotel, in Midtown, popping Vicodin, then having panic attacks about all the pills he’d just ingested. “I’d go from the warm, opioid feeling of blissed out, everything is OK,” he says, “to, Holy shit, what was that? Did I just feel my heart start to stop?”

“I knew he was having psychological problems,” recalls John Stirratt, Wilco’s bassist. “But I didn’t know how much the pills were playing into that.”

Soon after the sessions wrapped, Tweedy entered rehab, an experience he chronicles in Let’s Go. “I think to stay healthy you have to keep some of that stuff in the front of your mind, and certainly some of the desperation and anguish of that situation,” he says, as he finishes a Topo Chico.

On “Having Been Is No Way to Be,” from his new solo album, he contends with the fact that some fans and critics have wished aloud that he were still on drugs, as he was when he recorded some of Wilco’s most well-received albums. “They’ve said that in forums where I’m not necessarily supposed to see it,” he says. “It’s a horrible fucking thing for anybody to say about anybody.” It’s as if they’re telling him, “I don’t want you to be happy, because I like the music you made when you were less whole, when you were less of a human.” If that’s the case, “go back and listen to those records if that’s what you fucking want to do,” he adds. “They exist. They’re not going anywhere.”

He embraces the opportunity to confront these feelings on stage. “My comfort level with being vulnerable is probably my superpower,” he writes in Let’s Go. “Gutting myself in front of strangers…was exactly what I always wanted to do with my life.”

LUNCH ARRIVES AT 1 p.m. Vegan burgers and fries from Native Foods Café. Schick and Mark Greenberg, manager of the loft, join us at the table. Greenberg notices some glue in Tweedy’s hair from yesterday’s music-video shoot for “Some Birds,” from Warm, the concept for which Tweedy developed and tries to explain.

From what I can tell, it involves—bear with me—a dorky Tweedy with a bad, short haircut who walks by a salon; sees a cool, long-haired shadow Tweedy inside; enters; and has his hair magically lengthened—a reverse haircut, basically. Then, somehow, both Dork Tweedy and Cool Shadow Tweedy end up wearing the same outfit, then exit together, looking alike. “On the record, there are all these references to twins,” Tweedy says, between bites of his burger. “There’s this concept of a shadow self that I’m preoccupied or obsessed with.” Hence why he also plays double-neck guitars throughout the video.

The idea is stupid, but funny stupid. That’s the point; that’s why Tweedy likes it. At times, he has been portrayed as controlling, difficult, uneven—an image propagated most widely by Sam Jones’ 2002 documentary, I Am Trying to Break Your Heart, about the fraught recording of Yankee Hotel Foxtrot. And, to be fair, Tweedy can come across as “kind of a prickly character,” says Glenn Kotche, Wilco’s drummer. Onstage, Tweedy has jokingly imitated bad interviews with German reporters (“Why are the guitars so loud?”) and reprimanded talkative audience members (“What can I do to be of better service to you?… Tell me what I need to do to get you to listen”). And the British press, to Tweedy’s annoyance, still likes to bring up a disastrous 1997 Wilco show in London, during which he stopped playing and called the crowd a bunch of “snotty Brits.” In truth, though, “he’s very easygoing and funny,” Kotche adds, “and I don’t know if the public always gets that.”

Tweedy is the kind of guy, I discover, who will give you shit about the questions you have taped inside your notebook and for forgetting the name of comedian Don Rickles, upon seeing a photo of him in the loft control room. He may also casually interrogate you about whether you’re going to write a hit piece about him. But he does so in a way that ingratiates himself with you. He’ll also discuss music and art with you as if you, too, create it on a high level, as if you can even begin to understand what goes through his head when he writes a lyric as head-scratchingly elegant as “She’s a jar / With a heavy lid / My pop-quiz kid / A sleepy kisser / A pretty war / With feelings hid / She begs me not to miss her.” You’ll appreciate him for allowing this illusion.

“They always say don’t meet your heroes, because they’ll disappoint you,” Nick Offerman says. “I would reassure the public that Jeff is an exception to that rule.” Moreover, R&B and gospel legend Mavis Staples, who collaborated with Tweedy on three recent albums, says that she was impressed by his “overall core values.” And that’s about as good a character witness as you can get.

“They always say don’t meet your heroes, because they’ll disappoint you,” Nick Offerman says. “I would reassure the public that Jeff is an exception to that rule.”

Tweedy has had his moments, no doubt. But in separate conversations, Kotche and Stirratt, each longtime Wilco members, agree that he has become more patient over time. In earlier years, if the band didn’t gel during a performance, they might have a spat on stage as they figured out the issue, Kotche says. “Now it’s a more even-keeled discussion about how we can make something better and trying things without pointing fingers.”

Later, in the control room, Tweedy asks Schick to play back an unreleased song that Team Tweedy offered, or wanted to offer, Mojo, the British music mag, for inclusion on a CD sampler. It’s lovely—big and spacious, with a simple lead keyboard melody. But it didn’t work out, for some reason. Maybe the wrong song file was emailed to Mojo or something? Tweedy doesn’t know for sure. Maybe “it’s just too beautiful,” he says.

THE NEXT AFTERNOON, back at the Wilco loft, Tweedy takes a Gibson harp guitar from a case and inspects it. It’s a fanciful-looking double-neck—a harp and an acoustic guitar melded together. He owns two of them, both made at the dawn of the 20th century. Still, “they’re built completely differently,” he says. “They’re so handmade.” He flips it around and back again, then strums.

Today, Tweedy’s garb is a bit goth: black blazer, dark shirt, dark jeans. But he isn’t broody or dour, nor is he typically. “He might scoff at the word happy, but he’s the most fulfilled that I’ve ever seen him,” Kotche says. A few weeks ago, Tweedy’s younger son, Sammy, left for college, making empty-nesters of Tweedy and his wife. “So far it’s pretty sad but also nice for Susie and me,” he says. In the kitchen, after he cases the harp guitar, his Apple watch suddenly lights up, and he digs his phone from his pocket. It’s Sammy, who apparently just got soaked in a rainstorm. “Oh, you need to buy an umbrella,” Tweedy tells him. They talk for a minute, then hang up. “See, I’m still needed a little bit,” he says.

He suffers migraines still, but he hasn’t relapsed to address the pain, no matter how bad it gets. Earlier this summer, his migraine medication went out of production, and before he could find a new one, he was scheduled to play 30 songs at a living-room charity show. He made it through about 13: “It was awful. I was crying in front of these people.” He tried to continue but made it through only another song or two. “They were all like, ‘You should go,’ ” he recalls. “I think it was uncomfortable for them to watch.” He’s on a new medication now, however, and doesn’t expect a similar meltdown on his solo tour this fall.

Though Tweedy is content with the general landscape of his life, he’s less so with his work, never mind Wilco’s acclaim or the praise sure to follow Warm and Let’s Go. “You can appreciate how good things are and still be really fucking dissatisfied,” he says. “I don’t get much satisfaction out of what I’ve done. I get more satisfaction out of doing.”

At the kitchen table, he summarizes a Gertrude Stein essay (“it’s probably super pretentious”) about masterpieces and why so few exist. “No creator is ever present during the creation of their masterpiece,” he says. “And her point is, you have to be able to get so deeply inside the process to disappear.” You have to be able to push away the outside world, the critics, the fans, the noise. Tweedy understands that on some level. He’s still trying to figure out a way to disappear.

In the meantime, though, Jeff Tweedy is just trying to be the best Jeff Tweedy that Jeff Tweedy can possibly be.

This story appears in the December 2018 print issue, with the headline “Solitary Man.”

For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!