One of my favorite moments in all of popular music occurs on Wilco‘s 2001 album Yankee Hotel Foxtrot, when the multi-instrumental noise on “Ashes of American Flags” segues into the opening drum progression of “Heavy Metal Drummer.”
That moment also happens to be the basis of two of the greatest moments ofI Am Trying to Break Your Heart: A Film About Wilco, the standout documentary directed by Sam Jones, which opened in June of 2002, 20 years ago this week. I Am Trying to Break Your Heart was not only present for the creation of one of its decade’s best albums, but it depicted some fascinating band dynamics at the same time ― all while looking absolutely fantastic.
The film, shot in beautiful black and white, is a making-of film about Wilco’s best album, Yankee Hotel Foxtrot, which had arrived the year before, just a week after the 9/11 attacks.
I Am Trying to Break Your Heart, named after the album’s leadoff track, depicts two big conflicts: Their fight with the label, which led to the album’s delay and shunting off to sister label Nonesuch Records, leading to Warner, essentially, buying the same album twice. It’s a rare moment of a band wrangling with a corporate label and the ending being happy.
The other big fight is the falling out between frontman Jeff Tweedy and guitarist Jay Bennett, seen here arguing about the famous song transition:
The Tweedy/Bennett falling out was even referenced on an episode of Billions:
In addition to all of the fighting and conflict, we get plentiful outstanding live performances of various Wilco songs.
The other most famous moment in the film has Tweedy talking about the beginning of “Heavy Metal Drummer” with his then-young son Spencer, segueing into the beginning of the song itself:
Spencer, now an adult, would go on to become a drummer and would play with his dad, even performing that very song:
Wilco has continued to crank out great albums every couple of years since, including a new one just this spring. I even had the opportunity to interview Tweedy back in 2019, when I asked him about I Am Trying to Break Your Heart, as well as another famous father-son moment when Ethan Hawke in Boyhood explains the Wilco song “Hate It Here” to his son.
As for Sam Jones, earlier this year he directed an outstanding documentary about Tony Hawk, called Tony Hawk: Until the Wheels Fall Off.
I Am Trying to Break Your Heart is not currently available to stream, but it remains one of the current millennium’s best documentaries about music.
CULTURE (counter, pop, and otherwise) and the people who shape it.