Wilco might be the only band in the American canon that’s hailed on one hand as sonic innovators and derided on the other as the epitome of “dad rock.” The Chicago-based outfit rose from the ashes of Uncle Tupelo, the sometimes-rowdy, sometimes-reverent roots-rock band that Jeff Tweedy and Jay Farrar founded together in Belleville, Illinois, in 1987. Uncle Tupelo dictated the terms of the nascent alt-country movement — No Depression, the title of its 1990 debut album, became the genre’s rallying cry — but infighting between Tweedy and Farrar caused the band to disintegrate just as it was gaining mainstream ground.

Farrar continued down his somber, devotedly acoustic path with Son Volt, while Tweedy and the rest of the remaining Uncle Tupelo lineup founded Wilco, to move in more exploratory directions. The path forward wasn’t easy, though. Wilco’s 1994 debut A.M. was a chip off the old Uncle Tupelo block, even though Wilco lightened up with shiny guitar licks and starry-eyed melodies. Two years later, though, Tweedy and the band raised the bar with Being There, an ambitious 19-song suite of stylistically diverse songs that blended soulful keyboards from new member Jay Bennett with elaborate orchestral arrangements, classic pop hooks, and heartbreakingly personal lyrics. Tweedy insisted that Reprise Records release the double album at the usual price ($17.98) instead of a more prohibitive one ($30), and Reprise agreed, on the condition that the band give up its royalties. Wilco lost an estimated $600,000 on the project, but Tweedy proved that he and his creative cohorts could deconstruct and reinvent traditional rock ‘n’ roll in subtly magnificent ways — at a time when hip-hop, dance-pop, and rap-rock dominated the pop-culture conversation.

Next, Wilco agreed to record an album of Woody Guthrie’s lyrics with English troubadour Billy Bragg. The resulting Mermaid Avenue sessions were hailed as masterpieces, but Bragg and Wilco clashed over the final mixes, cementing Tweedy’s reputation as a combative square peg actively resisting Americana’s tightly constrained circular hole. 1999’s Summerteeth furthered that feeling, as the band employed prodigious overdubs and balanced radio-ready hits with drug-hazed minor-key meditations. The 17-song collection still sounds deliciously weird today, but Summerteeth was the creative bridge between the old Wilco and the new, which fully bloomed on 2002’s Yankee Hotel Foxtrot.

The band spent three years on that album, hunkered down in their Chicago loft, and Tweedy alienated his band members by enlisting the help of multi-instrumentalist/producer Jim O’Rourke. He recommended drummer Glenn Kotche, who eventually edged out founding beat-keeper Ken Coomer; when Jay Bennett balked at the new material’s streamlined production, he was summarily fired. Once YHF was completed, Reprise Records rejected it outright, relinquishing the album’s masters to nullify the contract. A Sept. 11, 2001 release date cast an even more prophetic pall over the project.

These struggles were covered prodigiously in print, online, and in the tense, tragic documentary I Am Trying to Break Your Heart: A Film about Wilco. But that attention also emboldened the band to fully seize its own means of production; without a label to protest, they streamed Yankee Hotel Foxtrot for free on WilcoWorld.net before it was officially released. The album then went on to sell 600,000 units, to countless year-end best-of lists, and become a watershed moment in indie rock history.

After that, everything Wilco touched turned to gold. Between 2002 and 2004, the addition of accomplished multi-instrumentalist Pat Sansone, sound scientist Mikael Jorgensen, and avant-garde guitar hero Nels Cline turned Wilco into one of the most formidable lineups in the world. 2004’s A Ghost Is Born won two Grammys and debuted in the Billboard Top 10; 2007’s Sky Blue Sky was the first fully collaborative effort in Wilco history and cracked the Top Five. 2009’s Wilco (The Album), and 2011’s The Whole Love may be less audacious, but they’re still eminently enjoyable.

There have been low points. Jeff Tweedy battled substance abuse and severe depression in the mid-2000s; Jay Bennett died from an accidental overdose in May 2009, only weeks after he sued the band for breach of contract. Last year, just as Tweedy’s eponymous side project with his son Spencer took off, his wife was diagnosed with non-Hodgkin’s lymphoma. And last month, Wilco was first celebrated then chided for leading the charge to cancel Indiana tour dates in protest of the state’s religious freedom restoration act.

So who can foresee where Wilco will go from here? They could release rock-solid albums and tour well into the 2020s — or they could abruptly call it quits. Therein lies the beauty of the band’s 20-year history, though; listen in at any point on the spectrum and you can hear life’s fleeting joys and its minor tragedies. Elegant Americana fronted by the tender quaver of Tweedy’s voice. Squalls of guitar histrionics mixed with downtempo abstraction.

Uncle Tupelo was the scrappy little suburban band that singlehandedly birthed the blue-collar alt-country genre, and today Wilco is an international rock juggernaut. And they’ve achieved that status without ever following a single trend. Asked last September by Esquire magazine about his career, Tweedy said, “Uncle Tupelo was never cool, [and] Wilco was never cool … There was never an overarching desire or goal of being cool. The desire has been to get better and play better music, sustain ourselves doing this, and feel gratified making something.” As for that “dad rock” descriptor? Tweedy laughed: “Having that historical arc to look at, well, I’ve been called worse.”

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october, 2021