I Am Trying to Break Your Heart: A Film about Wilco by Sam Jones

I Am Trying to Break Your Heart
A Film about Wilco by Sam Jones


First Appeared at The Music Box, January 2004, Volume 11, #1

Written by John Metzger


No matter what happened with Wilco’s Yankee Hotel Foxtrot, Sam Jones had a great story to tell. At a time when bands try to homogenize their sound to fit within a particular market, Wilco took an opposing strategy. Each of its previous outings — A.M., Being There, and Summerteeth — showed remarkable growth and diversity, and taken together, they proved that Wilco was more intent on remaining courageously artistic than catering to any single niche. True, the group would have been thrilled to have achieved at least a little more commercial success, but it still has done quite well for itself considering the surprising turns its music has taken, the challenges it has tossed at its audience, and how bad the music business currently is at marketing such a thing. In essence, Wilco has put the emphasis back where it should be — on remaining true to itself as a band while crafting masterfully cohesive song cycles that break down barriers rather than erecting them. Indeed, if the industry wants the masses to purchase albums rather than download them, it needs to take a page from Wilco’s book and stop encouraging artists to release discs that contain a few disconnected hit singles surrounded by a bunch of filler.

So, when Sam Jones began documenting the creation of Wilco’s fourth outing Yankee Hotel Foxtrot, he had the basis for an entertaining narrative, but he wound up with something entirely different. Not only did he observe the band developing its second masterpiece, but he also witnessed the creation of one of the most consequential albums from one of the most significant ensembles in recent memory. The events that unfolded as it was being recorded, however, gave Jones an even broader tale, one that turns I Am Trying to Break Your Heart into a documentary that is as engrossing as its subject — one that should appeal to far more than just the band’s fans.

Without question, Jones is quite fond of Wilco and specifically its leader Jeff Tweedy. Consequently, there are moments during I Am Trying to Break Your Heart when his bias peeks through his portrayal of the group. Still, it’s not so blatant as to overshadow his portrait of the proceedings, though this is largely because Jones doesn’t delve into any of the various events’ minute details. He simply paints a sweeping chronological encapsulation of the entire affair, one that is as richly atmospheric as his subject’s music. In doing so, he captures the personality of Wilco as well as the personal dynamics among its members. He views the dissolution of a friendship, and he offers a glimpse at the thrill of performing as well as the tedium of industry meet-and-greets. He also highlights the battle between art and commerce, and the struggle of a group to straddle the line between the two while making an album about which it could be proud. Indeed, one isn’t likely to find a better documentary about what it is like to work within today’s music industry.

Released on DVD earlier this year, I Am Trying to Break Your Heart now boasts an entertaining, full-length commentary from Jones and Wilco that offers additional anecdotes and fills in some of the gaps within the film’s story. Also featured is a making-of documentary — that’s right, a documentary about a documentary — as well as numerous previously unreleased songs, alternate takes, and concert recordings — none of which is better than Jeff Tweedy’s stunning solo acoustic rendition of Sunken Treasure. While it’s true that the bulk of the bonus material is apt to appeal to only the most diehard Wilco fans, this doesn’t make the package’s centerpiece any less engaging or insightful. starstarstarstar

I Am Trying to Break Your Heart is available
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1 Star: Pitiful
2 Stars: Listenable
3 Stars: Respectable
4 Stars: Excellent
5 Stars: Can't Live Without It!!


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