Jones wanted to film the acclaimed alt-country/rock band making its fifth album, and Wilco leader Jeff Tweedy promised Jones unlimited access to the band's recording sessions. On the day he began filming in January 2001, Jones found the band in a somber mood, and was shocked when Tweedy told him that the band had just fired longtime drummer Ken Coomer. New drummer Glenn Kotche hadn't even been told that the band was the imminent subject of a movie documentary.
That was hardly an auspicious beginning for the sessions, or Jones' film -- but it was a harbinger of much bigger turmoil to come. Over the course of the next 14 months, Wilco made the boldest artistic statement of its career, Yankee Hotel Foxtrot, only to have it rejected by its label, Reprise Records. Wilco multi-instrumentalist and songwriter Jay Bennett was ousted from the band. And thanks to Jones' determination and dogged camera work, that professional and personal drama is captured on film, and presents true human nature in a way that no prefabricated reality show could ever hope to.
One of the things that makes the film so immediately arresting is its universal appeal. While Wilco fans will certainly love the intimate look at the band's creative process, the studio scenes are representative of the challenges any creative and talented band faces while striving to make the best album possible. "We're deconstructing things right now," Tweedy says at one point, as the band experiments with electronic noises, alternate rhythms and disparate mixes. "There's no reason not to destroy it, and that's liberating and exciting."
It's also sickening -- figuratively. With tough creative choices and multiple egos involved, there's a number of tense, unsettling confrontations that play out, primarily between Tweedy and Bennett. At one early juncture in the film, the two men try to agree on the best way to remix the song "Heavy Metal Drummer." They each make passionate arguments that make perfectly good sense, but it's clear from watching the exchange that Tweedy and Bennett might as well be speaking foreign languages to each other. When the debate finishes, Tweedy promptly excuses himself and goes to the bathroom to throw up, and Jones records all of it, right down to Tweedy wiping the vomit off his chin.
That sense of witnessing such private, often unflattering moments surfaces throughout the film, but there's never any sense that the Wilco principals are conscious of the camera. Tweedy uncomfortably mumbles his way through a meet-and-greet backstage where he's asked ridiculous questions; Wilco manager Tony Margherita makes an impassioned defense of his band's integrity in a tense phone call with Reprise Records brass; and Tweedy sheepishly realizes he has no cash and can't buy his wife and two children dinner at an Iron Skillet restaurant on a tour stop.
I Am Trying to Break Your Heart isn't all emotionally downtrodden territory; there are a number of poignant snapshots that underscore the notion that the rewards of making music outweigh the burdens of the business. Bassist John Stiratt softly sings along with Tweedy during some downtime on the tour bus; the band plays some cathartic and riveting shows in the midst of its showdown with Reprise Records; Soul Asylum's Dave Pirner drops by backstage for some goofy post-show revelry; and one of Tweedy's sons slaps out the beat to "Heavy Metal Drummer" while Dad joyfully plays along.
The film's flaws are few, but they're noticeable since Jones came so close to making a damn near perfect film about music, a tough task that would put him in the company of DA Pennebaker's Don't Look Back and Martin Scorsese's The Last Waltz. There's a slow-motion segment showing the newly trimmed quartet (minus Bennett) walking on the edge of the Chicago River that's a bit heavy-handed and feels like music-video fodder -- and it's used twice in the film. And Bennett's dismissal is questionably handled; for all the unlimited access Jones had, there's no coverage of the meeting where Tweedy gave Bennett his pink slip, and the firing is dissected in a succession of awkward post-mortem interviews.
That said, I Am Trying to Break Your Heart should be required viewing for anybody interested in making music and/or the music industry -- and anyone who appreciates the grace of subtle storytelling that reminds us of the thrill of accomplishments and new beginnings. It's hard not to cheer for Wilco as they begin a new chapter at the end of the movie; I Am Trying to Break Your Heart lives up to its title in spots, but it's ultimately a gritty, heartwarming flick that's beautiful music for the eyes.
Email music news to Scott Jordan at firstname.lastname@example.org.