Watch the Tunes: I Am Trying To Break Your Heart

I cannot imagine the leap of faith that goes into even thinking about making a documentary film. Sure, there are aspects you can control, like picking an interesting subject to center things on, doing the legwork recording interviews, and settling on a distinctive aesthetic. But after that, you just shoot tons and tons of footage in the hopes that you’re in the right place at the right time to capture moments you can cobble together into something that’s larger than the sum of its parts, and stand as a lasting historical document. By that assessment, Sam Jones’s film about Wilco, I Am Trying to Break Your Heart, is a master class on capturing lightning in a bottle.

Shot entirely in black and white, Jones exercises the unfettered access he was given by the band to be present for seemingly every little bump in the road, of which there were many. There’s a tension brewing between Jeff Tweedy and Jay Bennett going into the mixing process that ultimately ends with Bennett getting booted out of the band not long after the album is finished. There’s a telling scene towards the middle of the film where the camera follows as Tweedy runs off to the bathroom to puke his guts up due to a Bennett-induced migraine. It’s one of the most emotionally raw things I’ve ever seen not because of the vomit but what comes after, when Tweedy just sits down next to Bennett and patiently tries to deal with Bennett’s nagging need to be creatively understood and validated. It’s a small thing, that scene after the bathroom, but it’s evidence of the kind of diplomacy a band like Wilco requires to move forward with their music and you can see the writing on the wall that one too many cooks are currently in the Wilco kitchen.

I distinctly remember when Yankee Hotel Foxtrot came out that there was a whole narrative attached to the marketing of it, however passively. The album had been passed over by Reprise (a subsidiary of Warner Brothers), leaked by the band as a stream on their website after Reprise handed them back their album for free, and eventually it was bought and distributed by Nonesuch (also a subsidiary of Warner Brothers). That’s all true, but Sam Jones does an excellent job of parsing out the story in order to connect the dots on how this all goes back to the misguided AOL / Time Warner merger, which plays out here much less boring than it sounds on paper. 

Yankee Hotel Foxtrot has more than earned its place in the canon of pop music, falling consistently near or at the top of just about every “Best Albums Of The 00’s” list ever made, but that the circumstances surrounding its creation were documented so artfully and completely is truly remarkable. I Am Trying to Break Your Heart is that rare film that seems to not only be present at every possible right place and right time, but also instinctively knows how to gracefully tell the story of this watershed moment in the life of Wilco.