Jimmie Dale Gilmore has been writing and playing songs for more than 50 years. His music eludes categorization, blending elements of folk, rock, country, blues and bluegrass. His recordings have earned three Grammy nominations in both Contemporary Folk and Traditional Folk categories and he was named Country Artist of the Year three years running by Rolling Stone Magazine. His high and lonesome vocal style, coupled with sometimes mystical and poetic lyrics, has led to musical brandings such as Outlaw Country, Sagebrush Soul, and Western Beat. Along with Joe Ely and Butch Hancock, Gilmore’s legendary band The Flatlanders has been credited as fathers of the Alt-country movement.

In recent years, Jimmie has collaborated and toured with Dave Alvin, The Flatlanders (Butch Hancock and Joe Ely), Colin Gilmore, Bill Kirchen, and others. Jimmie and Dave Alvin released a 2018 record called Downey to Lubbock. In June, 2024, Jimmie and Dave Alvin released TexiCali, their second collaboration album and will begin their US "We're still Here" tour in July, 2024.