I Am Trying to Break Your Heart

I Am Trying to Break Your Heart follows the creation and release of American alt-country rock band Wilco’s fourth studio album, Yankee Hotel Foxtrot. Directed by photographer Sam Jones, the black-and-white film captures a tumultuous period in the band’s history, documenting both their creative process and the unexpected challenges they faced.

The documentary begins with Wilco nearing completion of Yankee Hotel Foxtrot, but conflict soon arises between the band and their record label, Reprise Records. Despite the band’s critically acclaimed previous work, Reprise rejects the new album and drops Wilco from the label. This setback leads to a series of events that ultimately reshape the band’s trajectory.

In response to being dropped, Wilco makes the bold decision to stream the album for free on their website, an innovative move at the time. This strategy garners praise from fans and critics alike, attracting the attention of Nonesuch Records, which offers the band a new contract. Ironically, both Reprise and Nonesuch are subsidiaries of Warner Music Group, resulting in the parent company essentially paying for the album twice.

Throughout the film, Jones captures intimate moments of the band’s creative process, including recording sessions and live performances. The documentary also reveals internal tensions within the group, particularly the deteriorating relationship between frontman Jeff Tweedy and band member Jay Bennett, which ultimately leads to Bennett’s departure.

Beyond the band’s personal story, the film provides insight into the workings of the music industry, showcasing the challenges artists face when balancing creative integrity with commercial pressures. It features interviews with various industry figures and music critics, offering context to the band’s struggles and triumphs.