I have been a casual Wilco fan since right after I graduated from high school in the mid-90's. I've listened to a ton of their music and I love it, but I don't own all of their albums, I've never seen them live and I never knew much about who they were or where they came from. So this documentary, I Am Trying to Break Your Heart was a treat for me to finally see.
This documentary focuses on the recording of their classic album Yankee Hotel Foxtrot. They've achieved a level of success where their record label trusts them enough to record their album in a hotel room without a producer and they get a ridiculous amount of money to complete this project.
A movie like this is generally only really interesting to fans of the band, but this achieves a higher level of accessibility because it tells such a good story. It doesn't really matter who these guys are, they and the topic are interesting. The only thing I can compare it to in both format and visual style is U2's Rattle and Hum. Both films use black and white and they both are made up of recording footage, concert footage, interviews with a wide array of people and quite a bit of candidness. As we have seen in films like Let It Be, the recording process is not always an easy one. Big egos clash, communication goes out the window and feelings are hurt. That's all in the wonderfully titled I Am Trying to Break Your Heart, which incidentally is also the title of the first track of their album Yankee Hotel Foxtrot. They break each other's hearts consistently, which ultimately ends in someone leaving the band. As a matter of fact as of the time I'm writing this review, Wilco only has two original members left. Jay Bennett, who is prominently featured in the documentary, has strong opinions and seems to think of himself as an equal to front man Jeff Tweedy, is kicked out of the band by the end of the film. He died in 2009.
There are a couple of scenes in the film that almost make you think this might be a mockumentary. Comedian Fred Armisen, who had just started on SNL at the time, randomly shows up and has a conversation with Jeff Tweedy about superficial things like money and vacation homes. It's obviously done very tongue-in-cheek and also very funny. But most of the film is serious. Jeff Tweedy suffers from crippling migraines and there is a scene where he and Jay Bennett are arguing about semantics when he abruptly excuses himself to go throw up. The cameras are there for the whole thing following him in a shot that couldn't have been planned better by cinematographer Michael Ballhaus, but this didn't. As far as the cinematography goes on this film, IMDB lists eleven people. I'm guessing these are cameramen, because does a documentary need a cinematographer. Sam Jones' direction is excellent the whole way through. As is the editing by Erin Nordstrom. But the reason to see this is for Wilco. They've made great music for almost twenty years, and even if you've never heard them before, this film might make you a fan.