Gilmore is a native of the
Texas Panhandle, having been born in
Amarillo and raised in
Lubbock, Texas. In 1994, Gilmore teamed up with
Willie Nelson to contribute "Crazy" to the AIDS benefit album
Red Hot + Country produced by the
Red Hot Organization. Gilmore appeared as himself in
Peter Bogdanovich's 1993 film
The Thing Called Love, a love story about young songwriters in Nashville. He also had a small but memorable acting role in the 1998 movie
The Big Lebowski. He portrayed a bowler named Smokey, an aging, emotionally "fragile" pacifist threatened with a pistol by Walter Sobchak, "The Dude" Lebowski's best friend and sidekick (
John Goodman). He has also been a guest on
The Tonight Show, with host
Jay Leno, the
Late Show with David Letterman, ''
Late Night with/Conan O'Brien'',
Garrison Keillor's
A Prairie Home Companion on
NPR, and the
Fresh Air radio program with
Terry Gross. Gilmore's son,
Colin Gilmore, is also a singer–songwriter based in Austin. Gilmore's song "Braver Newer World" is featured in the 1995
Noah Baumbach film
Kicking and Screaming. In 2005, Gilmore released
Come on Back, ==Discography==