I Am Trying to Break Your Heart offers an impressive collection of extras that should please devout Wilco fans and draw new converts. Especially worthwhile is a feature-length commentary from director Sam Jones and the four members of Wilco. Jones injects considerable background about shooting, while the band gives quick tidbits about creating the record. The second disc contains a wealth of additional footage that combines both silly throwaway moments and impressive performances. The music highlights include Tweedy's solo performances of the Uncle Tupelo classics "Wait Up" and "Acuff-Rose," along with such full-band numbers as the recent "Pot Kettle Black" and Being There's "Why Would You Wanna Live." A separate section contains full versions of the film's two solo tunes -- "Not for the Season" and "Sunken Treasure." The remaining supplements include a short featurette, the theatrical trailer, and an extensive booklet. Sam Jones' elegant black-and-white photography works extremely well and receives a worthwhile DVD translation. The 1.85:1 anamorphic widescreen transfer does feature some grain at times, but it never distracts much from the presentation. The technological limitations of the low-budget documentary do appear here, which is an understandable element. This release would suffer considerably from a lackluster audio transfer. Luckily, the 2.0 channel Dolby Surround transfer effectively presents Wilco's music. The lack of a 5.1 channel Dolby Digital track, which could have enhanced the songs' complexity significantly, is slightly disappointing; however, the limitations of the original soundtrack probably played a role.