I Am Trying to Break Your Heart: A Film About Wilco is a black-and-white documentary film by Sam Jones which follows the American alt-country rock band Wilco through the creation and distribution of their fourth studio album Yankee Hotel Foxtrot. The film provides a unique insight into the politics of bands and their record labels, as well as an inside look at Wilco during the creation of what many critics describe as a landmark album. The title of the film shares its name with the first track of Yankee Hotel Foxtrot. With Wilco nearing completion of their album Yankee Hotel Foxtrot, conflict... arose between the band and its record label Reprise, a division of the Warner Music Group. Wilco's prior albums hadn't performed to Reprise's sales expectations and Reprise were concerned with how to market the new album. They consequently rejected the work and dropped Wilco from the label. With a completed album and no contractual obligations to Reprise, Wilco made the album available to download on their website. Awareness of the new album became apparent and Wilco's profile was rising. In response, another record label, Nonesuch Records, offered Wilco a new record contract.
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| Release date: | 2002 |
| Directed by: | Sam Jones |
| Runtime: | 92 Minutes |
| Producer: | Peter Abraham, Sam Jones, Gary Hustwit |
| Editor: | Erin Nordstrom |
| Music by: | Wilco |
| Cinematography: | Sam Jones |
| Genre: | Musical, Biography |