Jay Walter Bennett (November 15, 1963 – May 24, 2009) was an American multi-instrumentalist, engineer, producer, and singer-songwriter, best known as a member of the band Wilco from 1994 to 2001.

Nearing a master's degree in education at the University of Illinois, Bennett became a classroom teacher at Urbana Junior High, first as a substitute in 1985.

"[2] Tweedy and Bennett frequently argued over whether the album should be accessible to a general listener, or attempt to cover new musical ground.

[9] The suit came less than two weeks after Bennett publicly revealed that he needed hip replacement surgery which he could not afford due to his health insurance considering the situation a "pre-existing condition.

[11] On the weekend of his death, members of Titanic Love Affair and fellow bands and friends from its heyday had descended on Champaign-Urbana for a "Play or Pose Reunion" at which Bennett was expected to perform.

The Champaign County coroner reported about one month later that Bennett's death was accidental, and was the result of an overdose of the prescription painkiller Fentanyl.

[15] The post ended by encouraging fans to engage in some of Bennett's favorite activities: "listen to a Nick Lowe album, watch some MythBusters on Discovery, play Warren Zevon’s "Roland the Headless Thompson Gunner," rent Pay It Forward (one of his favorite movies), write a song with the TV on and the sound off," and focus on Bennett's loving spirit.

We will miss Jay as we remember him – as a truly unique and gifted human being and one who made welcome and significant contributions to the band's songs and evolution.

[17] Co-Directed by Gorman Bechard and Fred Uhter, this music documentary "delves into the life and career of Jay Bennett.

Released on Blu Ray and pay-per-view on April 19, 2022, and as part of a Record Store Day release with vinyl editions of Bennett's last two albums, Whatever Happened I Apologize and Kicking at the Perfumed Air on April 23, 2022,[18] "the new film does a wonderful job of capturing the quirkiness, inventiveness and brilliance of someone who never met an instrument he couldn't play.

"Jay Bennett's reputation never quite recovered from the battering it took in Sam Jones' documentary I Am Trying To Break Your Heart: A Film About Wilco, about the complex, lengthy gestation of 2002's Yankee Hotel Foxtrot in often painful detail, portrayed a band slowly pulling itself apart, with chief songwriters Bennett and Jeff Tweedy its twin opposing forces.