#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.