Jay Bennett from Chicago (1963-2009) was a member of Titanic Love Affair since 1991, named after a Billy Bragg lyric. After that band's demise, Bennett was invited to join Wilco as a lead guitarist. He was instrumental (pun intended) in their critically acclaimed albums Being There, Mermaid Avenue Volumes 1 & 2 with Billy Bragg, Summerteeth, and Yankee Hotel Foxtrot. He helped transform Wilco's sound with the addition of keyboards on Being There and later with his general studio wizardry on Summerteeth and YHF. He was asked to leave the band not long after the YHF recordings. He reunited with old friend Edward Burch and continued to release albums both with Burch and solo. He produced a wide array of artists from The Blues Travelers to Tim Easton. In May 2009, Bennett sued Jeff Tweedy for breach of contract, claiming that he was owed royalties.
Jay Bennett died in his sleep early Sunday morning, May 24, 2009, due to what was later revealed by an autopsy to be an accidental overdose of the prescription painkiller Fentanyl. He was 45.