#11. I Am Trying to Break Your Heart (2002)

I’ve heard all about how genius Wilco is and yet I’ve always found the music to rock-y and without distinction, so I watched this film last week just to prove its cult status is just that — a film with a niche following that didn’t belong on my list. Well, I was wrong. Despite the film having similar propagandistic qualities to Under Great White Northern Lights, it’s really well made, insightfully breaks down how a band makes its music, and even gets inside the musicians’ deepest feelings toward each other.

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Tom Roston
Tom Roston is a guest columnist for POV's documentary blog. He is a former Premiere magazine senior editor, who graduated from Brown University and started his career in journalism at The Nation and then Vanity Fair. Tom's freelance work has appeared in The New York Times, The Guardian, The Los Angeles Times, The Hollywood Reporter and other publications. He has written several Kindle Singles, including the bestselling Kindle Singles Interview: Ken Burns. Tom's current list of favorite documentaries are: 1. Koyanisqaatsi by Godfrey Reggio; 2. Hoop Dreams by Steve James; 3.Stories We Tell by Sarah Polley; 4.Crumb by Terry Zwigoff; 5. Montage of Heck by Brett Morgen