- From Magoffin County, (eastern) Kentucky.
- 1976, began performing with his father in a local bluegrass band and also worked briefly with the Goins Brothers.
- 1997, at age 17 replaced Keith Whitley as guitarist and lead singer with Ralph Stanley and the Clinch Mountain Boys (1977-86).
- 1986, left the Clinch Mountain Boys to form his own band and to return to school.
- 1986, released first album “Congratulations” (Acoustic Revival).
- 1988, released “Gravel Road” album (Rutabaga).
- 1989, released “Call of the Honky Tonk” album (Rutabaga).
- 1989, released “Singing with the Angels” album (Rutabaga).
- 1990, graduated from the University of Kentucky at the top of his class. The only bluegrass artist to play the Grand Ole Opry and deliver a college commencement address—all in the same year.
- 1990, released “I’ve Got a Good Memory” album (Rutabaga).
- After college, he moved to Nashville and wrote songs for Paul Craft Music. His songs have been recorded by Ralph Stanley, Jimmy Martin, Doyle Lawson and others.
- 1994, released Back Home album (Rebel).
- After finishing law school in 1994, he opened a private law firm in Goodlettsville, Tennessee and began his career as an attorney. He continued to make recordings and occasional performances.
- 1996, released In My View album (Rebel).
- 2002, released The Story Is … The Songs of Tom T. Hall album (Rebel).
- 2007, put his law practice on hold and returned to performing with the release of his Good News album (Rounder).
- 2010, released Heartache Looking For A Home album (Rounder).
- 2024, he was inducted into the Kentucky Music Hall of Fame.