I am Trying to Break Your Heart chronicles the creation of Wilco's fourth album, Yankee Hotel Foxtrot. While that may have been first-time director and acclaimed photographer Sam Jones' intent, the series of events that ensued during the recording would turn dramatic as Reprise Records decided to drop the band after YHF was delivered.
Jones' vision for the film hits the mark stylistically and with the surprising twists and turns that occur within the story. Shot in black and white, the wintry urban Chicago landscapes set the backdrop to which Jeff Tweedy and company set to make the most important record of their career. The band, holed up in their Chicago loft, set forth to produce a record without any outside interference. Jones shows us the increasing collaborative songwriting and creation process of Wilco, who arduously begin to craft a record that pushes their sound from simple alt-country ditties to modern experimental classics. We are able to see the skeletons of what would be the songs from Yankee Hotel Foxtrot through their many changes and much tinkering. From early recording to final mixing, the rising conflict between Tweedy and founding member Jay Bennett becomes quite clear. Upon completion of the album, Bennett is asked to leave the band, creating a humorous "behind the music" moment in the film.
Throughout the film, Wilco manager Tony Margherita paints the business picture for the audience, implicating the importance of this record for the band's career and his optimism for the record label's support. When YHF is delivered to Reprise, the optimism drops and we begin to see what would be one of the bigger major label fuck ups and ultimate examples of art vs. profit in today's industry. Without much reason or details, Wilco are dropped from Warner/Reprise and allowed to take the finished record elsewhere. Ironically, they take YHF to Nonesuch Records, whose parent company happens to be Time Warner.
Spliced throughout the film are interviews with local Chicago writer Greg Kot and Rolling Stone editor David Fricke, creating an historical context to the Wilco/Reprise dropping. It helps illustrate the absurdity of the situation while painting a grim picture of major labels today who aren't willing to spend the time to listen, understand and develop records like Yankee Hotel Foxtrot and bands like Wilco.
The film also lets us into the world of Jeff Tweedy, who has developed into one of America's finest songwriters. While often portrayed as serious and introverted, we get a glimpse into his lazy and aloof sense of humor that is both charming and endearing. Jones is able to show Tweedy's undeniable love for creating and performing music from his raspy ramblings with his ukulele backstage to voice cracking rock-outs on-stage.
I am Trying to Break Your Heart is rock & roll film for Wilco fans or music junkies and it manages to stay compelling throughout the one-and-a-half hours. It's a film that has drama but lacks sex and drugs. The film rather shows us the intricacies of creating music that is brave and challenging while facing the commercial limitations that clash with the interests of major record labels. A tremendous effort by first time director Sam Jones and another triumph for one of America's best bands.