I Am Trying to Break Your Heart: A Film About Wilco (2002)
- HD 1080
- Runtime: 92m.
- Status: Released
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- Languages: en
- Country: United States of America
- Director: Sam Jones
- Stars: Jeff Tweedy, John Stirratt, Leroy Bach, Glenn Kotche, Jay Bennett
- The I Am Trying to Break Your Heart: A Film About Wilco is featured in the top rankings of 2002
- #5 in Top Documentary Movies of 2002
A documentary by photographer Sam Jones documenting American rock band Wilco recording their fourth album Yankee Hotel Foxtrot. Originally intended as a showcase of the band's creative process, the film crew catches unexpected complications between the band and its record label and problems among the band members themselves.