Documentary director Sam Jones kept a “filmmaker’s diary” of his experience working on a movie about Wilco. The documentary would eventually be called “I Am Trying to Break Your Heart” but I remember a short period of time when the film’s web site called it “I’m Trying to Break Your Heart.” (The Internet Wayback Machine tells me the title was updated on wilcofilm.com some time between March 26 and May 23, 2002.)

Jones rolled out the diary to the site every couple of weeks after transcribing his handwritten notes from months before, starting with his writing to Wilco’s manager about the idea in October 2000. The final entry was uploaded in February 2002 after only getting through August 2001. Jones said, “We will continue to update the diary every few weeks with new entries, and have no intention of stopping until the entire story has been told.” Nevertheless, he did not persist. By 2004 the web site was abandoned and in 2005 the wilcofilm.com domain registration was not renewed.

Before he quit the project, Sam Jones contributed over 40,000 words to his filmmaker’s diary. Quite an effort! It would have been cool if he would have seen it through, but even in an incomplete state, it’s a really cool achievement. Inquiries to Jones were not immediately returned. We’re reprinting it here.

October 26, 2000

This film began with an idea and a letter. The idea was that a band that I really loved was probably in the studio recording their fourth record, and there should really be a movie about that. The letter, once I tracked down his address, was sent to the band’s manager, Tony Margherita. It said, in many more words, basically the same thing. But everything that happened next was probably largely a result of those many more words, because they had a conviction that has carried me through the project. I wrote in the letter that I believe Wilco is a band that will stand the test of time. Like The Band, the Clash, Big Star, the Velvet Underground, and Bob Dylan, Wilco makes dense, emotional, timeless records that will keep being discovered by new generations of music lovers.

November 3, 2000

I received a phone call from Tony Margherita, Wilco’s manager, who told me that the idea sounded very promising, and that Jeff Tweedy and Tony would like me to fly to Chicago to meet them. I asked Tony about the schedule and he informed me that the band was about 30% into the making of the new record, tentatively titled “Here Comes Everybody,” and that they were recording entirely in their Chicago loft with no producer or record company personnel present. We talked more about what the band would be doing for the next year, and it seemed very feasible that I would be able to get the whole record-making process on film. Tony suggested I fly to Chicago the next week to talk.

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