10 Best Wilco Songs

During the fractious sessions for Yankee Hotel Foxtrot, Jay Bennett attempted several mixes and sequences of the album, none of which pleased Jeff Tweedy. Exasperated with how things were going, he invited Jim O’Rourke to have a go at mixing this song, and the members were so impressed with the results that they handed over all mixing duties to him.

But this was not the first transformation it had undergone. The band had also sacked drummer Ken Coomer halfway through recording, replacing him with Glenn Kotche, who added a whole array of non-conventional drum sounds. It’s these that truly give I Am Trying To Break Your Heart its weird, disconnected quality.

As piano melodies are played slightly out of tune and instruments seem to be hit at random in the background, one of the band’s greatest ever songs is almost buried under a wall of wilful experimentation. Almost, but not quite. They leave just enough there to make this a truly majestic album opener.