I Am Trying to Break Your Heart (2002)

USA, 92 minutes, documentary
Director: Sam Jones
Photography: Matthew Clark, Dave Colitre, Matthew J. Curry, Paul Hughen, Sam Jones, Joe Kessler, Dan Larkin, Jim Matlosz, Keith Pokorski, David Rudd, Alan Thatcher
Music: Wilco
Editor: Erin Nordstrom
With: Jeff Tweedy, John Stirratt, Glenn Kotche, Jay Bennett, Leroy Bach

As seems to happen so often in the history of making documentaries, a bunch of fortuitous stuff happened shortly after filmmaker Sam Jones turned on his many cameras for this strangely haunting rockumentary about alternative rock band Wilco and their album Yankee Hotel Foxtrot. First, poised on the verge of commercial breakthrough (albeit poised in that position for approximately the previous four years), the band's record label unceremoniously dropped them on receiving the album. That wasn't supposed to happen—this movie was probably intended to be about the commercial breakthrough. And then relations with one member of the band, Jay Bennett, imploded, and he was kicked out. That wasn't supposed to happen either.

It says something about the weird power of this compact black and white picture that these incidents, which in the normal course of things would have to count as something like "documentary gold," are instead the least of it, in terms of surprise or news value anyway. They even look a little like convenient scripted turns of event, for how neatly they are tied off and resolved by the end. It's not the music either, which has alternately thrilled me (when I first saw it) and sometimes (more recently) kind of embarrassed me for its diligent underachievement. On balance, I'd have to say I like the music a fair amount, though it is also a matter of mood. You have to have a taste for the kind of skronky, druggy exercises they indulge to "deconstruct" their workaday alt-country fare, not to mention for the workaday alt-country fare itself. No, I think it's something else that's getting to me here.



Among other things, whether it's trying to do this or not, the picture is enormously depressing on the music industry, at a critical juncture—the money men at the labels who really don't know what they're doing, the happy folks they hire to find the talent and do the PR, and the talent itself, in this case a motley of Midwestern, notably uber-repressed flannel fliers evidently working it all on sheer instinct, aka "heart." At a painful industry meet-and-greet after a solo show, head Wilco honcho Jeff Tweedy is peppered with inane questions about the new album. They've heard it's trip-hop, they want to know if it's more like A.M. or Summerteeth, they are behind it all the way, man. "It's got a lot of the drums and holes in the songs in it," Tweedy says by way of explanation. He's really trying to say something about the new tracks, but that's what comes out.

It's even more painful in the interactions between Tweedy and Bennett, who are a particular crystallization of the problem relationships that develop in such situations, and can come to have great force because they exist in such unhealthy environments. Bennett, who died in 2009, comes across as needy. He wants a more collaborative role in the songwriting with Tweedy, but he's not up to it, or Tweedy resists him, or they just can't click. It's hard to tell from the scenes we see, which have a little bit of all that and more going on. After his ouster, Bennett bravely declares to the camera that it's his belief that Tweedy was threatened by his talent. And that's even possible too, but the fascination is more watching two introverted behemoth incoherents attempt to collaborate. They don't even have basic vocabulary. It's a train wreck.

Lots of industry usual suspects pop up along the way here to praise the band: an extraordinarily smug David Fricke of Rolling Stone, label exec Howie Klein, producer Jim O'Rourke, music journalist Greg Kot. Wilco manager Tony Margherita cuts a funny figure, looking like he'd be more comfortable in an expensive downtown three-piece than the black leather jacket he affects, and bringing a constant stream of cynical insight to the horseplay of Wilco being dumped by Reprise, whose parent company is Warner, and eventually landing on Nonesuch, whose parent company is Warner. (As an aside, how can you not have a love/hate affair with the music industry?) Still, the elements of manifest gloating that crop up late here are a little unseemly—understandable, but they should have been resisted. It's just as easy to remake Reprise's case that they were dealing with a loser in Wilco—to make it even today, in full knowledge of all the aftermath.

Last but not least, there's the matter of that wonderful title, which drew me to this in the first place. It's so perfect—I Am Trying to Break Your Heart. It could be the title of almost anything, so many things. It's also a wry comment on the band's basic aesthetic of emotional release, sharing pain to halve it, standing in the pain instead of running away from it, etc., which is exactly where bands like Wilco in the "emo" style (there I said it) make their bread and butter. For me, Jeff Tweedy too often steps all over his own lyrics, they are so overwritten, and there's no end of evidence for that in this documentary. But he also has an undeniable way of concocting memorable phrases and images, and using them to whip up great bludgeoning walls of cathartic bliss. So it is the music too, after all, in a way, that makes this something I have to drift back to again now and then.