The state of music on the radio today is not good. This is not an opinion, this is a fact. Unless of course, bland, commercially sensitive artists with too much airplay is considered good. Most people believe that this is due to the slow corporatization of the music industry. Large multinational companies own multiple stations across the country and even in each market. Their main concern is profit, not creativity, so they latch on to current trends and play the heck out of them, leading to manufactured, unoriginal groups and fads. So where does a band like Wilco fit in? Good question. Wilco, sometimes described as alt-country, is admired by critics and has a loyal fan base, but garners little airplay. Their album sales are not spectacular, but they do make quality music. Bands like these need time to build a respectable catalogue and fan base, something that companies out for profit are not willing to invest. I Am Trying to Break Your Heart is from first time director Sam Jones, and tracks the recording of the album Yankee Foxtrot Hotel.

To say that Jones chose a fortuitous time in Wilco's history is an understatement. During his time with the band, he was able to capture the most tumultuous time in Wilco's history. He was there firsthand to watch as a band member left, the label dropped the band, and the subsequent album release to critical acclaim. Yankee Foxtrot Hotel went on to become the most successful Wilco album, commercially and critically, and even generated some airplay. Wilco is Jeff Tweedy, Jay Bennett, Glenn Kotche, John Stirrat, and Leroy Bach. In watching them practice, it is clear that Tweedy, the primary songwriter, creatively, is the driving force behind Wilco. Jones is able to show the fascinating process behind some of the songs, where the band literally "destroys" their composition. They lay down a basic tune, then add various instruments or sounds to see what the effect will be. Wilco figures it is their music, so they can do what they wish with it. Perhaps Jones used hindsight to pick some of his footage, but he chose to spotlight some of the minor arguments over the creative process between Tweedy and Bennett, who is no longer part of the band. It looks minor while happening, but makes a lot more sense given later events.

The bulk of the first half of the movie is preparation for the album. Jones shows Wilco in the studio recording and mixing, and shows Tweedy during some solo performances. He also uses much of their music, from the current and previous albums. What makes I Am Trying to Break Your Heart (taken from one of the songs from Yankee Foxtrot Hotel) unique is what happened as the release date neared. Wilco and manager Tony Margherita turned in their album. Soon after, the man who shepherded their career (and protected them) retired, and shortly after their label Reprise asked for changes. After they stated they were unwilling to make any changes, Reprise, a subsidiary of Time Warner, dropped the band. Because of the heightened awareness of the lack of creative artists in the industry these days and Wilco's reputation among critics, their case became somewhat of a cause celebe amongst the press. Then, Wilco decided to sign with Nonesuch, which, in a delicious ironic twist, is a different subsidiary of Time Warner. To Reprise's credit, they did allow Wilco to shop their record around to other labels. So Jones' documentary takes a large problem and shows how it acutely affects one band. I Am Trying to Break Your Heart is accessible this way to non-fans. It may not necessarily make Wilco fans out of all viewers, but it will certainly garner a newfound level of respect for them.