During one of the most notorious showdowns between a band and their label in recent memory, Reprise essentially told Wilco to talk to the hand when the Uncle Tupelo offshoot delivered their ambitious and experimental fourth album, Yankee Hotel Foxtrot. But Jeff Tweedy and the boys might have been a lot worse off had Reprise actually released the album.

For one thing, Wilco’s champion at Reprise, label president Howie Klein, had just been canned and the band didn't have many other supporters among the upper rungs. It’s likely Reprise would have left the band twisting in the wind even if they did have designs to release the album. For another thing, the original release date was supposed to be Sept. 11, 2001.

Instead of allowing themselves to continue being put through the major label ringer, Wilco managed to secure the rights to the recordings back from Reprise for free as part of a buyout. But within weeks of winning control of Yankee Hotel Foxtrot, Wilco faced a new challenge: unlicensed MP3s of all the songs began to surface on file sharing networks. In an effort to dissuade fans from downloading the low-quality recordings, Wilco began streaming the album in its entirety on their official website.

Meanwhile, they signed to Nonesuch (which, like Reprise, is a Time Warner affiliate) and officially released the album in April 2002. In the end, Wilco came out looking even more like mavericks: They recorded the album for Reprise, then got all the music for nothing and sold it back to a different subsidiary of the same company to distribute it for them.

Photo: Cowboy Pictures
Photo: Cowboy Pictures

It's understandable what made Reprise brass so nervous about Yankee Hotel Foxtrot. But anyone who had watched the band continuously evolve from the roots and Americana-based sound of their first two albums for the more extravagant climes of Summerteeth shouldn’t have been completely surprised.

Besides being the album on which Wilco completely open the door to just about every musical possibility that tickled their collective fancy, Yankee Hotel Foxtrot marks a major transitional point within the band's creative core. Tweedy and multi-instrumentalist Jay Bennett had long been close collaborators and they wrote and produced the bulk of the material on Yankee Hotel Foxtrot together. But the push and pull between Bennett's song-based approach and Tweedy's preoccupation with the overall concept led to Bennett's unceremonious departure from the band before they finished recording.

Tweedy must have really been feeling his oats at that point: He had also already kicked out drummer Ken Coomer and brought in Glenn Kotche. Filmmaker Sam Jones was on board to document the album creation process and wound up capturing a band coming apart at the seams in 2002's I Am Trying to Break Your Heart.

Of course, when Wilco were going into the sessions for the album, it represented a tipping point. From the end of 2000 to the beginning of 2001, they holed up in their hometown of Chicago along with engineer Jim O’Rourke (then a member of Sonic Youth) and began to rebuild their identity from the ground up. The band’s mix of complex arrangements and left-field production techniques is immediately clear during the album's first song, “I Am Trying to Break Your Heart." As the track swoops in on a dizzying swirl of guitar and keyboard textures, Tweedy's pop-savvy vocal melody and impressionistic lyrics are enveloped by junkyard-band percussion, atonal piano and psychedelic effects, setting the stage for much of what follows.

Although Kotche, O’Rourke and multi-instrumentalist Leroy Bach play everything from dulcimer to vibes throughout the album, it's safe to assume the lion’s share of the engagingly off-kilter sounds emerged from the mind and/or fingers of Bennett, who had tried out nearly every guitar known to man during the sessions. From the fractured organ behind Tweedy’s plaintive singing on “Radio Cure” and the drunken synth lines of “War on War” to the distorted guitar that ushers in “I’m the Man Who Loves You,” the specter of Bennett lingers.

But all of the album’s rampant eccentricity would be for naught if there weren’t for the tightly structured tunes at the center of it all and Tweedy's top-form lyrics. The vivid, self-reflective imagery of the rock fable “Heavy Metal Drummer” could have come from a vintage Pavement tune except for the fact that Stephen Malkmus would likely never allow himself to be so vulnerable with a line like “I miss the innocence I’ve known.” And the colorful, free-flowing non-linearity Tweedy employs on tunes like “Ashes of American Flags” feels like a doorway into a new world of possibilities.

Yankee Hotel Foxtrot became and remains Wilco's best-selling album and it's their most thrilling blend of tunefulness and experimentation. Tragically, Bennett died in 2009 after accidentally overdosing o prescription drugs. And while he and Tweedy went on to make more great albums on their own, their 2001 collaboration remains a high-water mark.

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