I Am Trying to Break Your Heart (2002)

If you’re a Wilco fan like me, the title of this should’ve triggered a pretty immediate association. I Am Trying to Break Your Heart: A Film About Wilco is a documentary about the controversy and chaos surrounding Wilco’s attempts at releasing their seminal 2001, wait, 2002 album Yankee Hotel Foxtrot. The album was completed in 2001, but after their Warner record label deemed it too abstract to sell, Wilco shopped around the album to various buyers, explored the In Rainbows thing before it was In Style, and eventually signed with Nonesuch (consequently, and an irony not lost on the band, another Warner label). Tensions rise between band members Jeff Tweedy and Jay Bennett throughout the recording process, and director Sam Jones captures every moment in black and white, with intimate shots of band meetings and backstage arguments over two second effects at the end of a song. 

For fans like me, the documentary is essentially 92 minutes of unfettered Wilco pornography. However, do not be put off by the seeming minutiae of a band you may have no interest in. In the legacy of Don’t Look Back, I Am Trying to Break Your Heart is an extremely privileged foray into the drama and comedy of personalities that drive the creative process. Tweedy could just as easily have entered into comedy, and a lengthy conversation with Fred Armisen at a San Francisco event provides just another case of warranted levity to the film. I Am Trying to Break Your Heart is a great documentary about one of the few great rock bands at work today.