I Am Trying to Break Your Heart, Sam Jones’ 2002 documentary about Wilco making Yankee Hotel Foxtrot, is a fantastic film about the creative process, art vs commerce, and the many difficulties of the music biz:
Building on three critically acclaimed records and a reputation for phenomenal live shows, the band seemed poised to cement its reputation as one of the great American rock groups. So how is it that one year later, with completed record in hand, the band found itself rejected by its corporate label and missing two of its original members? First-time filmmaker and award-winning photographer Sam Jones was on hand, chronicling this turbulent chapter in Wilco’s history as it unfolded.
Throughout the film, Jones tempers the backstage dramas and unfathomable corporate shenanigans with inspired live performances, as frontman Jeff Tweedy and company perform songs from Yankee Hotel Foxtrot and previous Wilco albums. Shot in luminous black and white, I Am Trying to Break Your Heart is a riveting portrait of a band making the best music of its career.
If you’re never seen it, I Am Trying to Break Your Heart: A Film About Wilco is streaming for free this week as part of Oh You Pretty Things “Free Movie of the Week” series which is going on through out the COVID-19 crisis. It’s a partnership with Film First who are currently working on a new 4K transfer of the film.
It’s stream through May 12 and they’re also accepting donations; 50% of all tips go to My Block, My Hood, My City, a non-profit chosen by Wilco that is helping local Chicagoans during the COVID-19 crisis. Remaining funds will go toward the film’s restoration. Watch over at Oh You Pretty Things and you can check out the trailer below.
Need more alt-rock docs? Here’s a dozen suggestions of films to stream right now.
Subscribe to Brooklyn Vegan on
And here’s a gallery of Wilco at their 2019 Solid Sound festival: