In 2001, when Wilco was finishing up their fourth studio album (Yankee Hotel Foxtrot), considered to be one of the best of the decade, their record label decided to dump them. What was the band to do? An inside look into the politics of bands and labels—as well as an up-close profile of Jeff Tweedy and the other talented musicians—I Am Trying to Break Your Heart offers much to think about and much to enjoy, especially the treasure trove of early and alternate versions of some of the tracks. Sam Jones (Off Camera with Sam Jones) shot over 80 hours of black-and-white footage of the alt-country/experimental rock band to make this, his first film.