AllMovie

I Am Trying to Break Your Heart is a enjoyable documentary about the band Wilco, and the making of the album Yankee Hotel Foxtrot. The film will certainly appeal to the band's fans, but there are enough interesting people and dramatic events documented here to draw in viewers unfamiliar with Wilco's music. Front and center is Jeff Tweedy, the band's disheveled, musically adventurous lead singer, who has a somewhat antagonistic relationship with the band's talented guitarist, Jay Bennett (who looks a lot like Philip Seymour Hoffman). The two have several protracted creative arguments about the music before things reach the breaking point. Jones shows us Tweedy puking before a show, and the singer nonchalantly explains that he does it all the time and has since he was a child because of migraines. Tweedy is a low-key kind of guy, so it's exciting to see how animated he gets during the band's live performances, which Jones captures with energetic flurries of camera movement. The film shows how the record business can undermine a band that isn't easily pigeonholed musically. The baffled response their label has to their painstakingly produced work exemplifies this point. For the sake of his soul, Tweedy proclaims, he "can't entertain any of their half-assed, fearful, frightened bulls___." The film's tone is generally upbeat, considering the ordeal the band went through. There are casual fun moments between the band members, and it concludes with a satisfyingly ironic happy ending.