Jay Bennett was a multi-instrumentalist, singer and songwriter. From 1994 through 2001, he was a member of the popular rock band Wilco, leaving the band after the completion of their landmark Yankee Hotel Foxtrot album.

Bennett's conflicts with Wilco frontman Jeff Tweedy formed the basis for the documentary I Am Trying to Break Your Heart: A Film About Wilco. Bennett died in bed on May 24, 2009, at the age of 45.

A few weeks before his death in May of 2009, Bennett filed suit against former bandmate Jeff Tweedy, alleging breach of contract and failure to pay artist's royalties. Bennett's $50,000 suit focused on Bennett's lack of compensation for his participation in the I Am Trying to Break Your Heart documentary. Tweedy commented that he felt the lawsuit was unfounded, as he did not personally produce the film.Chicago Sun-Times: Sad coda to the Tweedy/Bennett Wilco partnership (May 5, 2009) Bennett also took issue with a sequence in the film featuring him and Tweedy arguing over the song "Heavy Metal Drummer."Riverfront Times: Jay Bennett Sues Wilco's Jeff Tweedy, The Internet Freaks Out (May 6, 2009)