1) “Via Chicago” from Summer Teeth(1999)
Ride the smooth slide guitar all the way through this song. This lyrical masterpiece talks about darkness in a light and resilient way. “I dreamed about killing you again last night / And it felt alright to me. Your cold, hot blood ran away from me to the sea.” The mismatch between the sound of the music and the lyrics sets up a beautiful contrast. Finally, another reason this song is so great are the little outbursts of guitar and drums throughout, as if the song has a volcano under the surface that is barely being held back by the placid surface.
2) “At Least That’s What You Said” from A Ghost Is Born (2004)
This song features a raging guitar solo that will knock your socks off. The song starts off with a brief lyrical section that sets the stage and the context for the guitar to follow. Lyrics are just an aside in this song, though. The guitar does all of the talking. This one has got to be the top Wilco song for guitar enthusiasts!
3) “Side With The Seeds” from Sky Blue Sky (2007)
Side With The Seeds is lyrically packed full of imagery and takes a relatively post-modern view of belief. As with most great Wilco songs, this one also has a guitar solo that feels like it is decomposing into serene madness at various points. “The treetops nod, the rain applauds, the park grows dark, and the swings all slowly die. But you and I will be undefeated by agreeing to disagree. No one wins but the thieves, so why side with anything?”
4) “Wilco (The Song)” from Wilco (The Album) (2009)
This song feels like a tumbleweed rolling forward in a stiff and unrelenting wind. The beat will carry you forward and bounce you along. One of the more pop-y Wilco songs, Wilco (The Song) is also one of the most catchy and it will stay with you for the rest of your day… “Wilco… Wilco… Wilco, I love you baby… ” The squealing guitar will make you grin.
5) “I’ll Fight” from Wilco (The Album) (2009)
This song sounds like it came out of the 70’s and it has a folky sound. The steel guitar gives it a bit of a cowboy feel, but not enough to make it country. Like a well-seasoned steak, you’ll be filled up and finish feeling satisfied after listening to this song. What makes this a contender for best Wilco song of all time is the fact that each of the elements are so beautifully balanced.