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By Tim Merrill | August 2, 2002

Near the beginning of “I Am Trying to Break Your Heart,” Sam Jones’ engrossing documentary on the acclaimed band Wilco, manager Tony Margherita proclaims: “This is the moment. This is the record; if not, it’s a tragic missed opportunity.” This, rock fans, is what’s called foreshadowing.
If you read any mainstream or alternative music press at all, you know that the aforementioned record is Yankee Hotel Foxtrot. During the year covered by Jones’ film, the most difficult of the band’s career, this record is anticipated as Wilco’s critical and commercial peak, where all their hard work and personal travails will pay off. As it turned out, the record would be exactly that. But getting there was a hell of a traumatic journey, and Jones admirably pares it down to 94 tastily tuneful, occasionally dissonant minutes. Wilco fans will feast; others might go hungry. But who cares about them? They’ll always have Total Request Live.
At this point, of course, one thing is established about Yankee Hotel Foxtrot: “Dude, that album is amaaazing.” But in fairness to the bean-counting corporate androids at Reprise Records – whose response to the record was utter bewilderment, and worse – it must be said that Yankee Hotel Foxtrot is a bit of a strange one. It’s certainly nobody’s idea of a commercially viable product in these debased days of Britney, Puffy and the dreaded Creed. (A moment’s digression: What is it that’s so epically vomitous about Creed? Leaving aside their generic religiosity, one is tempted to dismiss them as our era’s answer to Styx, Kansas and/or Journey – except Creed hasn’t come up with a song half as memorable as “Fooling Yourself,” “Point of Know Return” and/or “Lovin’ Touchin’ Squeezin’.” A question for another documentary, or perhaps for God himself: Do we really need Creed?) Anyway, the guys in Wilco certainly ain’t getting by on their looks – it’s truly all about the music.
In gorgeous, high-contrast black and white imagery, Jones shoots the band – led by singer-songwriter/frontman/genius Jeff Tweedy and multi-instrumental cohort Jay Bennett – jamming, rehearsing and recording in the relaxed intimacy of their Chicago loft. Tweedy, a prickly but generally agreeable presence, explains that his intent with the new record is to deconstruct his own songs to the point of abstraction, thus liberating…something. “We made it, so it’s ours to destroy,” he insists. In the early going, however, it’s nice to hear the songs in unplugged, undeconstructed folk arrangements, before all the “experimental” studio processing. (Actually, the album isn’t all that weird, not with the catchy one-two punch of “Heavy Metal Drummer” and “I’m the Man Who Loves You,” and the ear-pleasing Beatleisms of “Poor Places.”)
It’s the experimentation, the deconstruction, that gets the band into trouble with their label. The storm clouds start gathering at a Tweedy solo show, when the bandleader is cornered backstage by a couple of weaselly WEA executives who ask him “what the record is like.” Tweedy’s response, essentially, is that it doesn’t sound like any other Wilco album; when he starts expounding on odd drum sounds and “holes in the songs, open spaces between what’s supposed to be the music part,” the silence is quite deafening. Finally Tweedy can’t explain himself anymore, and walks out.
Reprise Records, see, was embroiled in some sort of AOL-related corporate nightmare at the time, and in no mood for what critic Gregg Kot calls “a masterful, dense, artistic statement.” After presenting the label with the tapes, the Wilco camp hears nothing for two weeks. When they finally do get a call, they learn that Reprise wants “changes,” they have “ideas.” Tweedy is adamant – the album is finished, take it or leave it. Reprise not only leaves it, they also drop the band from their roster, on the very same day head honcho Howie Klein exits the label.
Things look bleak for Wilco; no doubt Jones was thanking the Documentary Gods for all the unforeseen drama the situation brought. The plot thickens even more when, before our very eyes, the relationship between Tweedy and Bennett falls apart. The breakup begins with a technical disagreement in the studio in which neither man will relent, but both try to keep it under control; it’s fascinating to watch Bennett cook his own goose because he simply can’t be quiet. He ends up explicating himself to death. Jones’ access extends to peering over the bathroom stall as Tweedy pukes after this argument, not-so-subtly depicting Tweedy’s decision to fire his musical partner.
At a tour rehearsal – in which the band plays a terrific version of “I’m Always in Love” from 1999’s pop-friendly Summerteeth – the tension won’t dissipate, and worsens when Tweedy pointedly tells Bennett he likes the song better with only one guitar. Guess whose? “I thought it felt great,” Bennett shrugs, and we the listeners agree. But when Tweedy replies “I think the two-guitar thing may be obsolete”…well, it will be in this particular group.
With Bennett gone, the band dynamics naturally change. Tweedy is now in complete control. Bennett comes off as a bit bitter, of course – but that may be because the overall perspective here is clearly Tweedy’s. “Jeff was threatened, he wanted the band back,” Bennett asserts, and he’s probably right. But Bennett is certainly talented enough to front his own band, so he should be alright.
As a “year-in-the-life” portrait, Jones’ film works beautifully. Ultimately, though, it’s limited by being little more than a very in-depth look at the making of…a piece of entertainment. Wilco’s greatest triumph may be that, in finally signing with avant-garde mainstay Nonesuch – another WEA label – they corner AOL Time Warner into paying for the same album twice. (The music-press publicity didn’t hurt; Yankee Hotel Foxtrot debuted in the Top 15 and has been Wilco’s bestselling, not to mention most critically beloved, album to date.)
Sure, “I Am Trying to Break Your Heart” may not have much to offer non-fans of the band. But then again, in 30 years’ time it might seem as incisive a document of its time as, say, “Don’t Look Back” or “Gimme Shelter.” As a study of how the current corporate idiocy impacts one man’s art, it’s priceless.

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