The moment "Jesus, Etc." starts playing, something shifts.
"Skyscrapers are scraping together" — when that phrase arrives in the ear, it becomes clear immediately that this is not a straightforward love song, not a conventional rock song. That a band could wrap uncertainty and anxiety in something this beautiful was not something I had expected.
That was my introduction to Wilco.
A Chicago band led by singer-songwriter Jeff Tweedy, Wilco has walked its own path at the edge of American rock since its formation in 1994. Country to psychedelic, noise experiment to delicate folk — the musical journey these albums trace is less the story of a band's commercial development than the record of one musician's interior exploration.
🎸 Uncle Tupelo — Where Wilco Came From
To talk about Wilco, you have to start with Uncle Tupelo.
Formed in Belleville, Illinois in 1987, Uncle Tupelo brought together Jeff Tweedy and Jay Farrar, two songwriters who fused the traditions of country, folk, and bluegrass with the energy of punk rock. The music they made contributed decisively to the formation of what would eventually be called alternative country. Albums like No Depression and Anodyne are still cited as foundational texts of the genre.
But the creative relationship between Tweedy and Farrar deteriorated over time. Their musical visions diverged; their personal relationship broke down. The details have never been fully disclosed, but the outcome was clear: in 1994, Farrar left the band, formed Son Volt, and Uncle Tupelo dissolved.
Tweedy did not stop. With bassist John Stirratt, drummer Ken Coomer, and multi-instrumentalist Max Johnston — all Uncle Tupelo members from its final period — he formed a new band. That band was Wilco.
"When the band ended, I didn't feel much," Tweedy has said. "I just started thinking about what to do next." That forward momentum, quiet and steady, was characteristic of everything that followed.
🌾 The Debut Album "A.M." — Starting Point in Country Rock
On March 28, 1995, Wilco released their debut album A.M. on Sire/Reprise Records.
The record carried forward, relatively directly, the sound Tweedy had developed in his Uncle Tupelo years. Country, roots rock, and pop mixed naturally; the result was warm and accessible. Brian Henneman of The Bottle Rockets played guitar on the recording — Wilco did not yet have a permanent lead guitarist.
A.M. performed solidly. The Uncle Tupelo audience followed Tweedy to the new band without much difficulty, and the critics received the album well. But something larger was already forming inside Tweedy. A.M. was a departure point, a place to start from. The real Wilco was becoming visible only in outline.
🎹 Jay Bennett Joins — The Moment the Music Opens Up
After the recording of A.M. was complete, a new member arrived.
Jay Bennett was a multi-instrumentalist — guitar, keyboards, and virtually anything else you placed in front of him. His addition to Wilco changed the band's musical possibilities immediately and permanently.
Tweedy recognized quickly what Bennett brought. Not just the ability to play many instruments, but the ability to think architecturally about music — to arrange, to design sound, to make a song become structurally more complex without losing the thread. This was what Tweedy needed.
Their creative partnership deepened fast. Tweedy brought melody, concept, and the essential Wilco character. Bennett brought the means to realize those ideas in richer, more layered form. The collaboration that produced the next several albums was built on this division of creative labor.
The 2003 documentary I Am Trying to Break Your Heart, filmed during the making of Yankee Hotel Foxtrot, captures this partnership and its tensions with unusual candor. "Jay could realize things I'd imagined better than I could," Tweedy has said. "That was sometimes wonderful and sometimes frightening."
🌍 "Being There" — The Ambition of a Double Album
In 1996, Wilco released Being There as a double album.
This was a statement. Releasing a two-disc record in the commercial climate of the mid-1990s was not without risk; the label was skeptical. But Tweedy insisted. "We had things to say that wouldn't fit on one record."
The music moved significantly beyond A.M. Country and roots rock remained in the foundation, but psychedelic rock, power pop, and soul entered the mix. Horn sections, layered arrangements, and experimental passages appeared alongside more direct songs. The gap between A.M. and Being There was audible and deliberate.
Rolling Stone named Being There the best album of its year. Critics called Wilco "the great hope of the next generation of American rock." The band had stepped entirely clear of the alternative country label. From this point, Wilco was not the successor to anything. It was its own thing.
🎼 The Woody Guthrie Project — The Miracle of Billy Bragg & Wilco
Between 1997 and 1998, Wilco participated in one of the most unusual projects in their history.
Nora Guthrie, daughter of Woody Guthrie, had been developing a project to set her father's unrecorded lyrics — notebooks of verse he had left behind, unmusicalized — to new music. She approached British folk-punk musician Billy Bragg. Bragg in turn brought Wilco in as co-creators.
Woody Guthrie is an originary figure of American music — the author of "This Land is Your Land," the great songwriter of labor and social justice and the lives of ordinary working people. To take his words and bring them back to life with new music was a cultural project as much as a musical one.
The 1998 album Mermaid Avenue was nominated for the Grammy Award for Best Contemporary Folk Album. The sequel, Mermaid Avenue Vol. II, released in 2000, received the same nomination.
The project revealed something important about Tweedy's relationship to American musical tradition: a deep respect for its roots combined with an impulse to engage with and extend that tradition rather than simply preserve it.
🦷 "Summerteeth" — Experimenting With Pro Tools and Layered Sound
In 1999, Wilco released their third studio album, Summerteeth.
This was the first full realization of a significant shift in how the band made music. Tweedy and Bennett used Pro Tools extensively, bringing in mellotron, synthesizers, and studio techniques that had not appeared in Wilco's work before. The album was built through layering and editing in the studio rather than through live band performance captured in real time.
"I started using the studio as a tool for discovering music rather than just recording it," Tweedy said. The process was itself a part of the composition.
The sound that emerged placed pop melodic beauty alongside dark, unsettled textures. The lyrics became more interior, more oblique. Summerteeth did not perform strongly commercially on its initial release, but it is today recognized as a pivotal moment in Wilco's development — the record that made the leap toward Yankee Hotel Foxtrot imaginable.
💔 "How to Fight Loneliness" — Jay Bennett's Piano and Pure Sadness
Among the songs on Summerteeth, the one that has stayed with me most deeply is "How to Fight Loneliness."
🎹 In the second half of the song, Jay Bennett's piano enters — and when it does, something shifts. The tone carries a particular kind of sadness, warm but quietly heartbreaking, the kind that doesn't announce itself but simply arrives and stays.
"Just smile all the time" — that line, carried on Bennett's piano, fades slowly outward. 🎵tu〜lu, tu〜lu ... the melody dissolves into silence, leaving behind a feeling that lingers long after the song has ended.
It is that kind of song.
The song's subject is the paradox at the center of social performance in the face of genuine loneliness: if you smile constantly, you will appear not to be lonely. The advice is accurate and completely hollow. That is the point.
Tweedy's long struggle with depression has been well documented; "How to Fight Loneliness" is often heard as a reflection of that inner life, expressed with the indirection that the best songwriting allows.
Bennett's piano and Tweedy's voice are in perfect alignment here. It is one of the finest examples of what their creative partnership could produce — and one of the most quietly devastating songs in Wilco's catalog.
📻 "Yankee Hotel Foxtrot" — The Masterpiece Their Label Threw Away
Yankee Hotel Foxtrot (2002) is one of the most important albums in the history of indie rock, and the story of its making and release is one of the most unusual in the music industry.
The recording took place in 2000 and 2001, at Wilco's Chicago studio known as The Loft. Tweedy and Bennett built a sound that incorporated noise, ambient music, and free jazz alongside more conventional song structures. Sound collage, dissonance, and the dramatic alternation of silence and eruption — what they made was unlike any previous Wilco record, and unmistakably Wilco.
Reprise Records, then owned by AOL Time Warner, reviewed the completed album and decided it had no commercial potential. They declined to release it. Wilco was dropped.
Tweedy's response was to post the album on Wilco's website for free.
Through 2001 and into 2002, Yankee Hotel Foxtrot was downloaded hundreds of thousands of times. Critics who heard it declared it a masterpiece. The consensus built rapidly. Nonesuch Records, also part of the Time Warner family, signed the band and released the album officially on April 23, 2002.
An album that had been abandoned by its label became one of the defining records of its decade.
✈️ "Jesus, Etc." — Skyscrapers Scraping, an Era Anticipated
The song from Yankee Hotel Foxtrot that has reached the widest audience and stayed the longest in memory is "Jesus, Etc."
"Skyscrapers are scraping together." That single image contains the whole song.
The song was written in 2000 and 2001, completed before September 11, 2001. Its official release came in 2002 — after. The image of skyscrapers trembling had, between the writing and the release, become literal in a way no one had anticipated.
Tweedy has been clear that the song was not written about 9/11. But many listeners heard it that way, and the song's atmosphere — uncertainty, unease, something large and structural shifting — was precisely what the moment required.
The arrangement is particular: strings and trumpet in soft conversation, Tweedy's restrained vocal, and the repeated phrase "Jesus, don't cry" — reaching toward something to hold onto while being unclear exactly what that something might be.
This is Wilco's most widely known song. It deserves to be.
🔥 The Dismantling and Rebuilding — What Jay Bennett's Departure Meant
The making of Yankee Hotel Foxtrot brought the tensions inside the band to a breaking point.
The creative relationship between Tweedy and Bennett had produced extraordinary music. It had also become, by the time the album was finished, untenable. Their visions for the band, and for each other, had come apart.
In 2001, before Yankee Hotel Foxtrot was officially released, Jay Bennett left Wilco — or was asked to leave; the accounts differ, and the truth was never fully clarified publicly.
Bennett died on May 24, 2009, of an accidental overdose of fentanyl. He was forty-five years old. His death sent a wave of grief through the Wilco community and well beyond. Tweedy described his feelings as "sad and complicated."
After Bennett's departure, Wilco rebuilt. Guitarist Nels Cline, drummer Glenn Kotche, multi-instrumentalist Pat Sansone, and keyboardist Mikael Jorgensen joined the band. A new six-piece Wilco existed.
Without that rebuilding, Chapter 2 would not have been possible.
_ _ _
Born from the ashes of Uncle Tupelo in 1994, Wilco spent eight years rewriting the map of American music — from the country rock of A.M. through the layered experiments of Summerteeth to the noise-and-poetry of Yankee Hotel Foxtrot.
All of it was the record of one musician's interior journey. Jeff Tweedy's interior journey.
"Skyscrapers are scraping together." That phrase still moves in my ear. 🎸
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