[8] On January 13, 2021, it was announced Skaggs had been awarded the National Medal of Arts by President Donald Trump, alongside fellow country musician Toby Keith.

At age 7, he appeared on television's Martha White country music variety show, playing with Lester Flatt and Earl Scruggs.

[10] Skaggs later joined The Country Gentlemen in Washington, DC, and J. D. Crowe's New South from Lexington, Kentucky.

In 1976, Skaggs formed progressive bluegrass band Boone Creek, including members Vince Gill and Jerry Douglas.

In addition to arranging for Harris, Skaggs sang harmony and played mandolin and fiddle in the Hot Band.

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.

He played the mandolin on the track as well as sharing vocals with Jack White, Brendan Benson, and Ashley Monroe.

[13] In 2012, Skaggs collaborated with Barry Gibb on the song, "Soldier's Son" which was released on Music to My Ears.

As of recent years, Skaggs continues performing at the historic Grand Ole Opry house in Nashville, Tennessee.

Ricky Skaggs was previously married to Brenda Stanley and has two children, Andrew and Mandy, from that marriage.