Gill attended high school at Oklahoma City's Northwest Classen High School. While there he played on the golf team and performed bluegrass in the band Mountain Smoke, which built a strong local following. After graduating from high school in 1975, he moved to Louisville, Kentucky, to join the band Bluegrass Alliance. Afterwards he spent a brief amount of time in Ricky Skaggs's Boone Creek band before moving to Los Angeles to join Sundance, a bluegrass group fronted by fiddler Byron Berline.