Tweedy was unhappy with how music from the initial recording sessions for the album was sounding, resulting in a lineup change for the band.
In the winter of 1999, Wilco lead singer Jeff Tweedy acquired a copy of Jim O'Rourke's 1997 album Bad Timing.
According to Tweedy:[1] [Bad Timing] ended up blowing my mind more than just about any album I'd heard in the last five yearsTweedy was invited to perform with a collaborator of his choice for the 2000 Noise Pop Festival in Chicago.
They listened to gramophone records by T. Rex, Phil Niblock, and Roy Harper; later that night they wrote material for the concert and agreed to meet the next day at the Wilco loft in Chicago.
O'Rourke invited Glenn Kotche, a drummer who played in a similar musical style, to the practice session.
He also sought to improve as a guitarist, taking influence from free jazz artists such as James "Blood" Ulmer.
[5] On May 14, 2000, Jeff Tweedy played the Noise Pop Festival at Double Door in a concert that polarized Wilco fans.
Natalie Merchant joined the band onstage, but left after Tweedy requested that she perform Utah Phillips' murder ballad "Rock Salt and Nails".
I became certain that this is how music is supposed to feel, and I got braver about doing something about it.Kotche re-wrote the drum parts for the album almost immediately upon his acceptance into the band.
In one instance, he reworked "I Am Trying to Break Your Heart" by adding parts played on hubcaps, crotales, and floor tiles.
[13] Tweedy felt that Bennett was "burning out" while mixing the album, and invited Jim O'Rourke to remix "I Am Trying to Break Your Heart".
O'Rourke continued to remix more songs, and attempted to increase the drama of the album by reducing the contributions by the backing members of Wilco.