He is trying to break our hearts

Following the band's high point, a rapturous, sold-out gig in December 1993 at Tramps in New York, at a time when Nirvana was rewriting the rules of commercial rock radio and it seemed anything -- even an Uncle Tupelo hit -- was possible, Farrar called the band's manager, Tony Margherita, and told him Uncle Tupelo was finished. Then Margherita called Tweedy and broke the news to him. With a messy split and an unsupportive music partner behind him, Tweedy would spend the next decade battling record companies and himself. But mostly himself, as he fought addictions, crippling migraines, and the need to purge Wilco of its original members in order to capture the sound he was chasing.

Following the very Tupelo-esque sounding "A.M.," Wilco delivered the multidimensional (and somewhat bloated) double CD "Being There," which signaled the band's inevitable break from alt-country. But to add to fans' confusion, in 1998 came "Mermaid Avenue," which sounded like a complete U-turn, harking back to an Americana hootenanny vibe. The project was spearheaded by Guthrie's daughter Nora, who had unearthed hundreds of her father's unpublished song lyrics. She handed them over to Bragg and Wilco, whose job it was to create the music and record, not a tribute album, but something more contemporary and unified. What they did was capture pure magic, an album of undeniable charm and appeal.

Here's how the unassuming centerpiece effortlessly came together: "[Guitarist Jay] Bennett banged out the three chords for 'California Stars' in his girlfriend's kitchen so quickly he was sure he'd lifted them off Springsteen's 'Nebraska' or some other cherished album. When Tweedy heard the demo, he did some tweaking; he accelerated the tempo and took the melody up an octave. In the studio, [drummer Ken] Coomer and [bassist John] Stirratt made it swing, and Wilco knocked out the finished version in two takes."

Of course, it's depressing to discover in Kot's account that tension between Tweedy and Bragg made a joint tour in support of "Mermaid Avenue" impossible, and that their respective managers often ended negotiations in trans-Atlantic shouting matches. The dysfunction hit its zenith when Wilco and Bragg appeared at the same New York festival, the 1998 Guinness Fleadh, but played separate sets promoting the same album.

But by that point there was tension everywhere, as Wilco I began to collapse. First to be shown the door was sideman Bob Egan. Soon Coomer and guitarist Bennett would be given their walking papers.

And then came the damaging -- both musically and emotionally -- recording of "Summer Teeth." Writes Kot: "What began in Austin [Texas] as a straight-forward live-to-tape band recording, ended up in Chicago as an elaborate two-man overdub extravaganza. It was Jeff Tweedy and Jay Bennett, a few cartons of cigarettes and a Pro Tools computer cocooned in a studio as they transformed songs of wretched despair into cathedrals of sound. In the process, they shut out the world and even their own bandmates."

Adopting a kitchen-sink approach to studio tinkering, the two became lost in a maze of sound effects, overdubs and lost tracks. Recalls Coomer, the soon-to-be-dismissed drummer: "Jeff didn't go to rehab, but he should've in my opinion. Jay was taking pain killers, antidepressants, and wasn't in much better shape. There really wasn't a band, just two guys losing their minds in the studio."

Tweedy himself was a physical and emotional mess, battling addiction problems, chronic and often debilitating headaches, bouts with depression and anxiety attacks that struck right before show time. And that highlights the only weak spot of "Learning How to Die"; Kot does not sufficiently answer -- or even address -- the riddle at the center of the book: Who is Jeff Tweedy and why, on a personal level, is he so miserable? Clearly the ailments blanket Tweedy's creative process, for better and worse, and Kot should have probed deeper into that uncomfortable territory in search of answers. (At one point Tweedy tells Kot, "I don't like talking about it.") Indeed, the troubling questions became even more relevant this April, when Tweedy checked himself into a rehabilitation clinic to battle his dependency on painkillers, forcing the release of "A Ghost Is Born" back by a month.

Musically, with the help of new Wilco guitarist/producer Jim O'Rourke, Tweedy brought the band back from the "Summer Teeth" edge with the gorgeous and now infamous "Yankee Hotel Foxtrot," an album that not only came to symbolize Tweedy's maturation as a songwriter, but was also a larger-than-life example of everything that had gone wrong with the increasingly consolidated music industry. Only in an industry run by fear would a senior vice president of A&R sit back and listen to "Yankee Hotel Foxtrot's" breathtaking 52 minutes, hit the pause button and conclude, "This isn't even worth shipping out to stores." But that's what they did at Reprise Records, in the spring of 2001. Not hearing any radio singles, the label told the band to shop it elsewhere. When the news leaked, Reprise was pummeled in the press. Trying to cut its losses, Reprise, which paid for the recording of "Yankee Hotel Foxtrot," made the rare gesture of giving Wilco ownership of the masters for free. Wilco then turned around and sold them to Nonesuch, a separate, although more appreciative, Warner Bros. entity. "The whole thing," manager Margherita recalls, "was like an insane dream."

Across the course of Jeff Tweedy's nearly 20-year personal and professional journey, you sense he gets that feeling a lot.

Editor's note: This story has been corrected since its original publication.

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