The story goes that Wilco were going through some inner turmoil during the making of Yankee Hotel Foxtrot, particularly between lead singer and guitarist Jeff Tweedy and fellow guitarist and composer Jay Bennett. Their original record label weren’t so impressed with the final result of their work, rejected it and told the band to get out of their faces, leaving them with an album to provide but no label to release it. Eventually things all fell into place. Wilco got signed again. The album, originally slated for September 2001, was physically released to the masses months later in May 2002. Critics ate it up, fans loved it. Still do to this day. It has gone down as one of the best albums of the opening decade of this century.
‘I Am Trying to Break Your Heart’ is the album’s opener. It’s seven minutes long. It takes about a minute of that time for the song’s main chord progression to make itself known after a sort of instrumental prelude of pianos, percussion and organs. Tweedy’s mellow voice comes in with the album’s first (and possibly most quoted) lines “I am an American aquarium drinker/I assassin down the avenue/I’m hiding out in the big city blinking/What was I thinking when I let go of you?”, and it all goes on from there really. You have to listen to it for that full experience.
Tweedy doesn’t have the greatest singing voice. Not soulful, or belting from the stomach or whatever. But it’s just perfect for the whole mood of the track. And the album in general. The vocal melody is the most simple thing. But it’s great. It will get in your head. And accompanied by the very full mix provided by Jim O’Rourke, it’s an enrapturing listen. It’s hard to not find yourself in a bit of a trance when hearing this. You probably won’t feel it on your first listen. It’ll sink in.
Above is the supposed demo of the tune, as recorded by Jay Bennett before it went through remixing for the album. Some prominent smooth Rhodes(?) piano in there, but not quite the same.