The filmmakers and talking heads of “Where Are You, Jay Bennett?,” a documentary released late last year, certainly think so. Directed by Gorman Bechard and Fred Uhter, the movie is a portrait of a former Wilco member who did not live long enough to see the album’s anniversary, whom Jones infamously depicted as the opinionated antagonist of “I Am Trying to Break Your Heart.”
Bennett, a guitar prodigy and math-minded studio wizard from the Chicago suburbs, was, at least in Jones’s telling, an anchor to Wilco’s past as earthy, alt-country barnstormers, and it was necessary for the band to cut him loose as it drifted toward its airier, art-rock future. Bennett joined Wilco in 1996, while the group was working on its epic sophomore double album “Being There,” and his predilection for intricately layered arrangements and fractured power-pop is all over the band’s follow-up, “Summerteeth,” from 1999.
Tweedy and Bennett had immediate, but ultimately explosive, chemistry. In the liner notes of the new collection, Tweedy admitted that when the virtuosic guitarist first joined, “I was really having a tough time picturing how that was going to sit next to my squeaky unsure voice.” The solution, for a time, was moving Bennett to keyboards, an instrument on which, in Tweedy’s words, “he was a little less sure of himself,” and thus a better fit for Tweedy’s wobbly poetry. Call it a practical power move.
Describing the sounds Bennett was drawn to, a phrase that is used more than once in the new documentary is “kitchen sink” — everything but, and sometimes including. Tweedy, on the other hand, found himself increasingly favoring avant-garde minimalism, which led him to records like the experimental composer Jim O’Rourke’s beautifully woozy “Bad Timing” or even “The Conet Project,” a compilation of eerie recordings from shortwave radio stations believed to be spy transmissions. (One track featured a woman’s voice droning, continuously, “Yankee … hotel … foxtrot.”)
