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A documentary about Wilco found the band—and the music world—on the brink 

Every day, Watch This offers staff recommendations inspired by a new movie coming out that week. This week: Don’t Stop Believin’: Everyman’s Journey has us thinking about other “inside the band” documentaries.

I Am Trying To Break Your Heart (2002) 
When former photographer Sam Jones signed on to document the creation of Wilco’s Yankee Hotel Foxtrot, he had no way of knowing the band was about to lose two of its members and be dropped by its label. Looking back a decade later, neither event turned out to be such a Bravo Foxtrot Delta—Wilco has persevered, releasing a new album every two to three years like clockwork, and few lament the loss of guitarist Jay Bennett or drummer Ken Coomer from the lineup of what’s really always been Jeff Tweedy And Friends. At the time, however, it seemed as if the very future of indie rock was at stake, and I Am Trying To Break Your Heart now functions beautifully as a time capsule from the period right before record labels’ dominance began to crumble in the face of digital self-distribution. The idea that a band wouldn’t be able to get its music heard by its rabid fan base now seems almost ridiculously quaint.

Because Tweedy is so guarded in front of the cameras, I Am Trying To Break Your Heart rarely succeeds at its stated objective. All the same, the film does feature some memorable behind-the-scenes blowups, including a control-room argument between Tweedy and Bennett (concerning the transition from “Ashes Of American Flags” into “Heavy Metal Drummer”) that could serve as a textbook illustration of destructive neediness. What’s more, Jones shot everything on black-and-white 16mm, making this one of the last documentaries ever made on celluloid; even when nothing much is happening, images of city streets as seen through a rain-spattered windshield, or of a bed-headed Tweedy driving with one hand and smoking with the other, are so iconically luscious that they serve as their own justification. Just 11 years later, it’s remarkable to consider both what we’ve gained and what we’ve lost.

Availability: Not currently streaming, but available on DVD and for digital rental/purchase.