Just listening to their music, Wilco seems like one of the last bands that would want to go to war against the suits of the music world. Even though they came out at a time when grunge was starting to hit big, their brand of mellow alternative country was more zany than anything else, never really going that far off the rails. Country was always the genre of outlaws though, and Yankee Hotel Foxtrot was the moment where they started going off the grid.
After the different bickering sessions between Jeff Tweedy and Jay Bennett, the band were starting to get severe pushback from their label for their next album, thinking that there wasn't anything to work with for single material. While the band felt that the music should be able to stand on its own as an album, some of their higher ups brought out the big guns, threatening to drop them from the label if they didn't come through with something that was a bit more radio friendly.
Rock and roll was never about rolling over though, and Wilco called the label's bluff, going independent for this record and turning it into one of the most successful indie releases of the decade. Wilco might not have been getting the same huge royalty checks, but they felt comfortable knowing that their label had learned a valuable lesson. You can try to jerk your artists around all you want, but they're still the ones that have the power to not give you their songs.