I recently got around to watching I Am Trying To Break Your Heart. Yes, I know that it is nine years old.
Chicago-based indie rock band Wilco had already earned its reputation as The Most Significant Band in Indie Rock and The American Radiohead by the time it recorded its fourth album, Yankee Hotel Foxtrot. Just about every periodical that published a "best of decade" feature last December ranked Yankee Hotel Foxtrot among the ten best rock albums of the Oughts. The documentary I Am Trying To Break Your Heart tells the now-legendary story of the album's production and release.
The documentary tells and inspiring story. Wilco's label, Warner Bros., gave it an $85,000 no-strings budget and almost unprecendented artistic license. Then, Wilco's champion at Warner Bros. retired, and his replacement did not share his predecessor's high opinion of the band. When Wilco turned into a brilliant-but-challenging record, Warner executives hesitated for two weeks, before issuing a vague request that Wilco make the album more listenable. Wilco, and particularly its lead singer Jeff Tweedy, bristled at Warner's demands, and negotiated a favorable separation with Warner, whereby Warner did not pay Wilco for the record, but Wilco was albe to leave the label with total ownership of its record, and was released from its contractual obligations to record more albums for Warner in the future. Because the album is so good, leaked copies became enormously popular on the internet, to the point where Wilco was able to tour on the strenght of its unreleased album. Eventually, Wilco ended up selling the record back to a different Warner subsidiary for three times the price that Warner had promised to pay for it initially. Everybody (except for Warner itself) won. But something about the documentary turned me off. A lot of Wilco's music is more easily appreciated than enjoyed, and a lot of the songs on Yankee Hotel Foxtrot are intentionally difficult and rough. Combined with the black-and-white footage and the shaky, ambient-noise quality of hand-held documentary filmmaking, it makes for a less than viewer-friendly experience.
The movie shows Wilco as they write a number of songs, perfect them, then take them apart and put them back together in a way that is more challenging for the listener. The documentary never explains why Wilco felt compelled to do that; why they weren't happy to release an album of beautifully played, pretty songs. When Jeff Tweedy and bandmate Jay Bennett have lengthy, obscure arguments about the best way to master a track, the stakes are never properly explained. This was one of many creative disagreements that led to Bennett being kicked out of the band, but its never made clear why Bennett and Tweedy felt that those particular artistic decisions - out of thousands and thousands in the band's career - were worth digging their heels in over. To their credit, when the memebrs of Wilco fight, they fight over artistic choices, instead of, say, sleeping with each other's girlfriends, but when even dedicated music fans cannot pick up on the subtle distinctions that led to the argument, the director's obligation should be to flesh it out a little bit more, and show us how Bennett and Tweedy's musical visions diverged.
Similarly, Warner's not-entirely-unreasonable request that Wilco make the album less intentionally difficult is dismissed as the worst sort of cliched meddling by rich know-nothing executives who wear suits to work, but the album might be loved more and appreciated less if Wilco had taken that advice to heart. Wilco's music can be heartbreakingly beautiful when they want it to be, which is why their ten-minute long songs that are intended to sound like headaches leave this listener wondering what might have been. It is interesting to note that the best live performance in the movie is of "Always In Love," which is off of Summerteeth, not Yankee Hotel Foxtrot, and the best live song from YHF is "Heavy Metal Drummer," the most lightweight song on the album. and many of YHF's songs sound even rougher in the movie than they do on the album. The documentary gets bogged down in the album's heaviness. This story of outsiders triumphing over their corporate masters makes for a surprisingly joyless documentary; Wilco comes across as very professional, but not very much fun to be around.
Still, the movie has a lot to recommend it. It is basically indie rock's "Don't Look Back," and most Wilco fans will leave the theater hungry even after seeing how the sausage was made. The film does an admirable job of building suspense out of events whose conclusions most viewers will already be familiar with, and the 16 mm black and white footage, though a little too self-consciously grainy at times, brilliantly captures the spirit and atmosphere downtown Chicago. I recommend it, but with reservations. It gives Wilco admirers what they're looking for, but is not going to win many new fans to Wilco's challenging style of music.