10. I Am Trying To Break Your Heart
https://www.youtube.com/watch?v=6z3hIYB8nec This 2002 film by Sam Jones follows rock band Wilco throughout the arduous process of releasing their acclaimed album "Yankee Hotel Foxtrot." A beautifully shot look into the often strained relationship between a band and their record label, "I Am Trying to Break Your Heart" sees a band on the brink of hitting it big but stuck in the procedure of getting the album in question released. Great music documentaries often showcase the internal strife of a band, and the film really represents the disintegration of Jeff Tweedy and guitarist Jay Bennett's relationship, which leads to the latter's ejection from the group. The knowledge that "Yankee Hotel Foxtrot" is arguably the group's best release makes the conflict with their record label all the more frustrating. "I Am Trying to Break Your Heart" perfectly executes the struggle to put out a piece of art while being held in the palm of a corporate gatekeeper.