Listful Thinking: Top 5 Wilco Songs

In which our hero agonizes before selecting his Top 5 Wilco songs...
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I was a little late to the Wilco bandwagon, having hopped not long after the arrival of Yankee Hotel Foxtrot. That record arrived in 2001, so while I don't go back to the beginning, I suspect there are many who came on board after I already had my seat.

The band has gone through numerous lineup changes over the years and now Wilco is really Jeff Tweedy's really awesome playground. He comes up with ideas and has incredible musicians capable of executing and occasionally improving upon them in the studio and on stage.

I've bought every Wilco record. I've purchased several of their Roadcase official bootlegs but have never seen them in concert. That was nearly rectified in October but... well, things happen, life changes, and next thing you know you're not seeing one of your favorite bands at your favorite venue on earth. If there is any good news in having lived through it, it's that I may yet see them one day.

This was a exquisitely painful list to make and I know some of my readers and friends will be in here with torches and knives, but here are my Top 5 Wilco songs.

  • "I Am Trying To Break Your Heart" - Wow, did this one throw me the first time I listened to it but in a matter that made me want to listen more, to keep listening until I could make sense of it. I am still working on that and loving every minute of it. 
  • "Summerteeth" - I hear a fragility and tenderness in this song that make the eyes of my ears swell with tears. I wish I could do a better job of identifying what it is that gets to me about this one but I am overcome with surges of emotion when I hear him sing, "It's just a dream he keeps having but it doesn't seem to mean anything." It's also a great tune with a hummable memory.
  • "Poor Places" - Yankee Hotel Foxtrot began with Tweedy & Co. trying to break your heart but this is the song from the album that accomplishes it. A despondent Tweed begins the song and the band builds tension that explodes into a cacophony of chaos and distress.
  • "Rising Red Lung" - If we were playing March Madness bracketology, this was the last song to get onto the list. What really connected this one to me was when the song was used in an episode of the last season of House. I don't think about that scene when I listen to it but somehow seeing the show reminded me of the song and it's been on heavy rotation ever since. The hushed nature of this hooked me and the line "As intimate as a kiss... over a phone" continues to confound.
  • "Passenger Side" - Wilco began as something of an alt-country outfit before spiraling in the many directions they have over their 20 years together. This is my favorite from their debut, a campy country song with wit: "You're gonna make me spill my beer if you don't learn how to steer..."