Via Chicago
Wilco, 1999, from Summerteeth. Solo by Jeff Tweedy.
On record it's a quiet folk song, but live the band tears through it with bursts of chaotic noise. Those clashes of noise and calm became a famous part of Wilco shows.
Via Chicago by Wilco is #7 in our ranking of the best Wilco guitar solos. The solo is played by Jeff Tweedy and the song was released in 1999.
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Sources
Who played the guitar solo on Via Chicago?
Jeff Tweedy played the solo on Wilco's Via Chicago (1999).