This is the fifth song I’ve featured from Wilco’s 2007 album Sky Blue Sky, all on Random Weekends. That’s nearly half of the album’s 12 tracks. The Random iTunes Fairy seems to have a thing for this record.
‘On and On and On’ is a deep cut on an album that is one of the band’s least heralded releases, but it’s quite meaningful to songwriter and lead singer Jeff Tweedy. Here’s what he had to say about the song in a 2016 interview: