Musician Ricky Skaggs He's got a new album out called The Three Pickers, and it features Skaggs playing along with Earl Scruggs and Doc Watson (also available on DVD). Skaggs started performing as a young child. He was considered a prodigy. His first number one single was "Crying My Heart Out Over You" in 1981, and he continued to have a string of hits throughout the eighties. But he fell out of favor for most of the next decade, coming back in 1997 with Bluegrass Rules! recorded with his backup band Kentucky Thunder. Skaggs has won many Grammy and Country Music Association awards.