Skaggs was born in Cordell, Kentucky.[9] He started playing music at age 5 after he was given a mandolin by his father, Hobert Skaggs. 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 banjo playing 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.[10]
Skaggs later joined The Country Gentlemen in Washington, DC, J. D. Crowe's New South. In 1976, Skaggs formed progressive bluegrass band Boone Creek, including members Vince Gill and Jerry Douglas. For a few years, Skaggs was a member of Emmylou Harris's Hot Band. He wrote the arrangements for Harris's 1980 bluegrass-roots album, Roses in the Snow. In addition to arranging for Harris, Skaggs sang harmony and played mandolin and fiddle in the Hot Band.
Skaggs launched his own career in 1980, achieving 12 No. 1 hits, 8 CMA awards, and 8 ACM awards. In 1982, he became a member of the Grand Ole Opry, the youngest musician ever to be inducted at that time. Guitarist and producer Chet Atkins credited Skaggs with "single-handedly" saving country music.[11] Skaggs is considered one of the pioneers of the Neotraditional country sub-genre.
In 1981, he debuted on Epic Records with the album Waitin for the Sun to Shine, which brought him to both the country and pop charts and produced two No. 1 hits.
Keeping with his instrumental heavy themes, he released "Country Boy" on the album of the same name. He also had Bill Monroe as a guest on this album.
Exploring a role as producer, Skaggs produced Dolly Parton's album White Limozeen, which started her comeback in country music.
Skaggs also guested on other albums. In 1995, he sang with Vince Gill on "Go Rest High on That Mountain", which later won CMA's Song of the Year and was determined by BMI to be the Most-Performed Song in 1997.
In 1996, 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.
In 2000, he shared the stage with Vermont-based jam band, Phish.[12] On March 20, 2007, Skaggs released an album with rock musician Bruce Hornsby.
In 2008, Skaggs released an album he recorded with The Whites on his Skaggs Family Records label.
Ricky Skaggs was previously married to Brenda Stanley and has two children, Andrew and Mandy, from that marriage.[15] Skaggs has been married to Sharon White of The Whites since August 1981.[16] They have two children; a daughter, Molly, and a son, Lucas.[16] Molly Skaggs is a Christian/Gospel singer.[17][18] Lucas is a multi-instrumentalist and session musician.[19]
In June 2020, Skaggs underwent quadruple bypass surgery in Nashville.
Skaggs in 2021 was awarded the National Medal of the Arts by President Donald Trump.
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
2012 Gospel Recorded Performance of the Year: "Singing as We Rise", Gibson Brothers with Ricky Skaggs
2017 Gospel Recorded Performance of the Year for song "Sacred Memories", Joe Mullins & the Radio Ramblers with Ricky Skaggs and Sharon White Skaggs
^Freeman, Jon (September 11, 2017). "How Ricky Skaggs Redefined Bluegrass and Brought It to the Mainstream". Rolling Stone. Retrieved July 21, 2019. ["Skaggs had his first country Number One, at age 27, in April 1982 with the weepy ballad “Crying My Heart Out Over You." It kicked off an incredible run of 12 chart-topping hits, placing him in the first wave of country's celebrated neotraditional movement along with George Strait, John Anderson and Randy Travis."]