When photographer and commercial director Sam Jones began plans to make I Am Trying to Break Your Heart, he envisioned a long-form rock video about the making of a Wilco album, Yankee Hotel Foxtrot. But right from the start, it seemed that Jones was destined to make a documentary about an extremely tumultuous period in the band's existence. The day before Jones started shooting, Jeff Tweedy, the band's singer-songwriter, called to say that they had fired Ken Coomer, and hired a new drummer, Glenn Kotche. Jones started shooting his film, in black-and-white, as the band recorded their inventive new album. He captured the tensions caused by creative differences between Tweedy and guitarist-songwriter-engineer Jay Bennett. Tweedy takes a break from making the album to go on a short solo tour. The band eventually completes the album, and after it's mixed by Jim O'Rourke, Tweedy is happy with it, and feels that the band has taken their music in a new direction. They send it to their label, Reprise, a division of Time Warner, and after two weeks of silence, the label, concerned about the album's commercial prospects, calls band manager Tony Margherita and asks for the band to make changes. Tweedy refuses, and Reprise decides to let the band take Yankee Hotel Foxtrot elsewhere. The band goes on tour, and stream the album on their website. Eventually the conflict between Tweedy and Bennett comes to a head. I Am Trying to Break Your Heart (named of a song on the album) documents the unexpected trials of the band, and their efforts to overcome them. The film premiered at the 2002 Los Angeles Film Festival.