In early 2000, the Chicago-based, country-influenced rock band Wilco began preparing for the recording of their fourth record, YANKEE HOTEL FOXTROT. Filmmaker/photographer Sam Jones went along with them to document a band at the height of its creative powers. What started as a simple documentary about the making of a record became a far more dramatic saga when, early in the recording process, drummer Ken Coomer left the band. Then, months later, friction between vocalist/chief songwriter Jeff Tweedy and multi-instrumentalist Jay Bennett resulted in Bennett`s departure. Adding to the setbacks, upon the completion of the record, Wilco`s longtime label, Reprise, rejected it and released the band from its roster. I AM TRYING TO BREAK YOUR HEART chronicles the critically-acclaimed band`s efforts to overcome these difficulties--efforts which eventually helped to make FOXTROT the band`s most successful release. Director Jones intimately captures the band on 16mm black and white film as they perform over twenty songs. More importantly, he also captures the pitfalls that develop when strong personalities embark on a collaborative creative endeavor. Fans of the band will have plenty to cheer about, while the uninitiated will come away with further cinematic proof of the difficulty of achieving the rock and roll dream.