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

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I Am Trying to Break Your Heart: A Film About Wilco
Directed by Sam Jones
Produced by Peter Abraham
Sam Jones
Gary Hustwit
Starring Jeff Tweedy
John Stirratt
Leroy Bach
Glenn Kotche
Jay Bennett
Tony Margherita
Music by Wilco
Edited by Erin Nordstrom
Distributed by Cowboy Pictures
Release date
Running time
92 minutes
Language English

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 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. Nonesuch Records is a division of Warner Music Group, like Reprise, so Wilco were essentially paid twice for the album by the same record company.

Other scenes depicted the breakdown of the relationship between members Jeff Tweedy and Jay Bennett, and Tweedy's debilitating migraines.


Film festival screenings[edit]

The film was submitted to and selected as part of the 'Official Selections of the Los Angeles, London and Stockholm International Film Festivals in 2002.

DVD releases[edit]

(Note that there are two versions of the film on DVD: The original two-disc set, and a newer version which omits Disc 2 and is generally less expensive.)

Disc 1

  • The film (digital transfer, 16x9 anamorphic presentation)
  • Feature commentary from director Sam Jones and Wilco
  • Original theatrical trailer
  • English subtitles for the hearing impaired

Disc 2

  • Over 70 minutes of extra footage, featuring 17 additional Wilco songs, alternate versions of songs from Yankee Hotel Foxtrot, live concert performances and new unreleased songs
  • I Am Trying To Make A Film making-of featurette


DVD Disc 2 bonus track listing[edit]

  • "Pot Kettle Black" *
  • "Busy Bee Monkey Song" (also known as "Monkey Mess")
  • "Why Would You Wanna Live"
  • "Pieholden Suite" *
  • "Acuff-Rose"
  • "Please Tell My Brother"
  • "Cars Can't Escape" *
  • "I'm the Man Who Loves You" *
  • "Magazine Called Sunset"
  • "Wait Up"
  • "Radio Cure" *
  • "Monday"
  • "Not for the Season"
  • "Sunken Treasure"

All songs written by Jeff Tweedy, except as noted *, written by Jeff Tweedy and Jay Bennett


External links[edit]