Watch I Am Trying to Break Your Heart: A Film About Wilco

I Am Trying to Break Your Heart: A Film About Wilco is a documentary film released in 2002 directed by Sam Jones. The film takes an in-depth look at the American rock band Wilco during the recording of their fourth studio album, Yankee Hotel Foxtrot, which was released in 2002. The movie follows frontman Jeff Tweedy, bassist John Stirratt, and multi-instrumentalist Leroy Bach as they work on the album, showcasing the conflicts and tensions that developed between the band members, the label, and the music industry at large.

The movie was filmed in black and white which helps convey the emotion and tension of the recording process. This style of filming is very effective at capturing the intensity of the band's struggles and personality clashes as they try to create what would become one of their most significant albums.

During the movie, we get to see the band's creative process and how Jeff Tweedy's songs are transformed into full-fledged arrangements. The guitarist and collaborator of many years, Jay Bennett, played a significant role in this process, but as we discover, had to eventually part ways with the band due to creative differences. This occurrence further adds to the tension displayed throughout the film.

The movie's pacing is excellent, and it never feels slow or uninteresting. It provides an astounding glimpse behind the scenes of a band creating a timeless masterpiece in spite of challenges and conflicts.

The film also shows how the record label responded to Wilco's album, and how it struggled to understand their music's direction. In the end, they refused to release the completed record due to a perceived lack of commercial appeal, leading to the band buying back the rights to the album, and releasing it on their own label. This culmination is not entirely surprising, as the film shows the wide range of styles and sounds the album experiments with, each track offering a unique atmosphere and mood.

The documentary also sheds light on the challenges facing small record labels, with industry insiders offering their thoughts on the state of music in the early 2000s. The film depicts how the band chose to take control of their music and release it themselves rather than risk losing its true meaning or transforming it for the commercial market.

Overall, I Am Trying to Break Your Heart: A Film About Wilco is a fascinating and intimate portrayal of the creative process and the music industry during an increasingly challenging era. Watching the band's battles with the label and decision to release the album on its own terms feels even more notable in retrospect, given the time passed as the film approaches two decades since its release.

If you are a fan of Wilco or music documentaries, you owe it to yourself to give this film a watch. It provides an insight into one of the decade's most influential alternative rock bands, and the inspiration behind their creative process.