I Am Trying to Break Your Heart & Wilco’s XRT Free Fourth of July Concert [Watch]

The Wilco story of 2002 is my favorite music biz story of all time. Why? Because it represents the struggle of musicians against the combined forces of corporate America.

Related: See Wilco’s I Am Trying To Break Your Heart At The Music Box Theatre This Thursday

When Wilco appeared at the 93XRT Free 4th of July Concert at Taste of Chicago, they were supposed to be on the verge of releasing Yankee Hotel Foxtrot. However, their record label was not impressed. They wanted something more commercial. How about some more hit songs? Wilco stuck to their guns. They parted ways with their label and tried to find a new label to release the album. On the side of the stage at the Petrillo Band Shell that July 4th, I made an innocent query, “When is the new album actually available for people to go out and buy?”

Jeff responded, “That’s a good question.” And he said it in such a way that it was pregnant with implications. That moment is captured on the Wilco documentary, I Am Trying To Break Your Heart, which also shows Frank E. Lee bringing the band on stage for one of our most memorable live events.

Wilco signed with a smaller subsidiary of the label that dropped them. Yankee Hotel Foxtrot debuted on the charts at #1 which, I should point out, is plenty commercial. At the end of the year, you chose it as the number one album of 2002 in the XRT Listener Poll.

A dramatic story. Tweedy vs. Goliath. With a happy ending. In 2002.

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