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Watch the Tunes: I Am Trying To Break Your Heart

On April 8, 2016


There is an absurdly vast selection of music movies and documentaries available on Netflix, Hulu, HBO Go, and on and on and on. But it’s hard to tell which ones are actually worth your 100 minutes. Watch the Tunes will help you pick what music doc is worth your Netflix and Chill time every weekend. This week’s edition covers I Am Trying To Break Your Heart, which is streaming over at Amazon Prime.

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capture moments you can cobble together into something that’s larger than the sum of its parts, and stand as a lasting historical document.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.

It’s noted by a number of people early on in I Am Trying To Break Your Heart that, after three critically lauded but financially underperforming albums, there was a lot of pressure on Wilco to “make the next step” which amounts to “Make the record label some money.” The feeling that this was a band capably on the verge of breaking wide open was apparently palpable enough for photographer Sam Jones to step in and start filming the making of that album in the vague hope that it ended up being that “next step.” It’s wild to think that there was a time when Yankee Hotel Foxtrot, the album which sprang from these sessions, could have ever been anything but the masterpiece it’s seen as now, but here we get to see the the album in its infancy when no one knew the true potential it had. Everyone on the band’s side of things has faith, certainly, but like all works of art you just never know how it’s going to be received until it’s out there being consumed.

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.

Profile Picture of Chris Lay
Chris Lay

Chris Lay is a freelance writer, archivist, and record store clerk living in Madison, WI. The very first CD he bought for himself was the Dumb & Dumber soundtrack when he was twelve and things only got better from there.

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