I Am Trying to Break Your Heart

Music documentaries, like all good documentaries, are dramas. I Am Trying to Break Your Heart documents Wilco, the “alt-country-turned-experimental rock band” (their description), as singer-songwriter-guitarist Jeff Tweedy and his collaborator, guitarist-keyboardist Jay Bennett, wrestle with the muses, recording-studio technology, their record label and each other to produce their fourth and latest album, Yankee Hotel Foxtrot.

With its concert and its recording-studio footage subtly charged and occasionally sparking with power struggles, I Am Trying to Break Your Heart is this generation’s echo of Let It Be (the 1970 film documenting the creation of the Beatles’ album it’s named after — and the creatively fatal conflicts among Paul McCartney, John Lennon and the rest of the band). Director Sam Jones mutes the living Technicolor of Let It Be, telling this tale instead in the tones of his beautifully framed black-and-white cinematography.

The Wilco of this documentary becomes something like a dysfunctional family. The issue is power. As lead singer and primary songwriter with a few solo albums and tours under his belt, Tweedy has the power. But Bennett takes a seat behind the mixer and begins to call the shots in the studio, mistaking himself for the McCartney to Tweedy’s Lennon. The resulting less-than-ordinary tragedy verges close to a VH-1 “Behind the Music” episode. Jones’ honest art, though, redeems it from TV tabloid melodrama.

After a year of blood, sweat and tears shed over Yankee Hotel Foxtrot, Wilco’s record company requires marketing-driven changes for the album’s release. Tweedy refuses and I Am Trying to Break Your Heart becomes a more archetypical drama: today’s music industry’s David-and-Goliath fable.

Contrary to its title (from a Wilco song), I Am Trying to Break Your Heart rarely does. But there’s real life-sized conflict, suffering, pity and redemption. Not heartbreaking, but for fans of Wilco, Tweedy, documentaries and music-industry insiders, it may be heartfelt.


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James Keith La Croix writes about film for Metro Times. Send comments to [email protected].

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