Skaggs started performing as a child and was considered a musical prodigy. After a string of country hits in the 1980s, he returned to bluegrass, performing folk renditions of his own country hits. In 2003, Skaggs spoke to Fresh Air host Terry Gross about growing up in the music industry and playing with Bill Monroe and Earl Scruggs.
He originated the staccato, three-finger banjo technique that became known as the "Scruggs style." He got his start playing with Bill Monroe's band in the 1940s, and then teamed up with guitarist Lester Flatt (fronting The Foggy Mountain Boys). The two penned and recorded the tune "Foggy Mountain Breakdown," which was used on the Bonnie and Clyde film soundtrack and was one of the first crossover hits of the genre. They also recorded "The Ballad of Jed Clampett," the theme song for the sitcom The Beverly Hillbillies. It topped the charts in 1962.