Skaggs was born in Cordell, Kentucky. He started playing music at age 5 after he was given a mandolin by his father, Hobert. At age 6, he played mandolin and sang on stage with Bill Monroe. At age 7, he appeared on television's Martha White country music variety show, playing with Lester Flatt and Earl Scruggs. He also wanted to audition for the Grand Ole Opry at that time, but was told he was too young.
In his mid-teens, Skaggs met a fellow teen guitarist, Keith Whitley, and the two started playing together with Whitley's banjoist brother Dwight on radio shows. By 1970, they had earned a spot opening for Ralph Stanley and Skaggs and Keith Whitley were thereafter invited to join Stanley's band, the Clinch Mountain Boys
In the 1990s and 2000s, Skaggs went back to his bluegrass roots, and also experimented with new sounds. With his band, Kentucky Thunder, he is a perennial winner of Grammy Awards and International Bluegrass Music Association for best bluegrass album.
2000 Recorded Event Of The Year: David Grisman, Ronnie McCoury, Frank Wakefield, Sam Bush, Bobby Osborne, Jesse McReynolds, Ricky Skaggs & Buck White for Bluegrass Mandolin Extravaganza
2002 Instrumental Group Of The Year: Ricky Skaggs & Kentucky Thunder
2003 Instrumental Group Of The Year: Ricky Skaggs & Kentucky Thunder
2004 Instrumental Group Of The Year: Ricky Skaggs & Kentucky Thunder
2005 Instrumental Group Of The Year: Ricky Skaggs & Kentucky Thunder
2006 Instrumental Group Of The Year: Ricky Skaggs & Kentucky Thunder
2008 Recorded Event of the Year: Everett Lilly & Everybody and Their Brother; Featuring Everett Lilly, Bea Lilly, Charles Lilly, Daniel Lilly, Mark Lilly, Marty Stuart, Rhonda Vincent, Billy Walker, Ronnie McCoury, Rob McCoury, David Ball, Charlie Cushman, Larry Stephenson, Joe Spivey, Eddie Stubbs, Jason Carter, Dickey Lee, Freddy Weller, Mike Bub, Rad Lewis, Andy May, Darrin Vincent, Marcia Campbell, Clay Rigdon, Eric Blankenship and Bill Wolfenbarger (artists); Charles Lilly & Bill Wolfenbarger (producers); Swift River Music