Bootleg Monday: Jeff Tweedy and Jay Bennett, Chicago, IL 7/25/99

The falling out between Jeff Tweedy and Jay Bennett was well documented. I Am Trying to Break Your Heart: A Film About Wilco, the documentary about the recording of Yankee Hotel Foxtrot features scenes, which openly shows the relationship between the two breaking down. Bennett was ultimately kicked out of Wilco, but it is hard to ignore the contribution that he brought to the band. During his tenure, Wilco released, arguably their three best records in Being There, Summerteeth and Yankee Hotel Foxtrot.

With that said, let’s flashback to 1999. Wilco released Summerteeth on March 9, 1999 and had released Mermaid Avenue the previous year. During the summer of ’99, Jeff Tweedy and Jay Bennett were booked as a duo for the Old Town School of Folk Music Festival in Chicago. Their 21 song set features stripped down versions of Wilco songs as well as some choice covers. This is a must listen for any Wilco fan and really shows the dynamic that existed between Tweedy and Bennett.

Jeff Tweedy and Jay Bennett
Sunday, July 25, 1999
Old Town School of Folk Music Festival
Chicago, IL

Click here to listen to the show.

  1. Introduction
  2. James Alley Blues
  3.  She’s A Jar
  4. New Madrid
  5. Blood of the Lamb
  6. Down in the Willow Garden
  7. Auld Triangle
  8. Another Man’s Done Gone
  9. Hesitating Beauty
  10. Via Chicago
  11. Sugar Baby
  12. I Got You
  13. Forget The Flowers
  14. I’m Always In Love
  15. The Lonely 1
  16. Summerteeth
  17. Pecan Pie
  18. True Love Will Find You In The End
  19. Casino Queen
  20. Encore Break
  21. California Stars
  22. Hoodoo Voodoo

 

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