- From Lexington, Kentucky.
- Sonny and Bobby Osborne are cousins. His grandfather is their uncle.
- Besides music, his passion is training and showing Tennessee walking horses, a family tradition.
- 1980, formed his first band called Thousandsticks Express.
- 1986, formed his second band Eastbound.
- 1988, went full-time with his band.
- 2006, appointed head of the Bluegrass and Traditional Music program at Hazard Community & Technical College in Hyden, Kentucky.