Ricky Skaggs discusses Christmas music, The Grand Ole Opry and the legacy of Bill Monroe

December 10, 2025

Listen to a conversation with the virtuoso multi-instrumentalist, vocalist, and bandleader, Ricky Skaggs. Born in Kentucky in 1954, Skaggs has played a central role in shaping modern bluegrass and country music. A child prodigy, he first performed on stage with Bill Monroe at age six, and at age seven he appeared on national television with Lester Flatt and Earl Scruggs. 

Before turning 18, Skaggs had already performed with many of the greatest legends in bluegrass. At age 15, he and his childhood friend Keith Whitley joined Ralph Stanley’s Clinch Mountain Boys.

In the 1970s, Skaggs’ musicianship helped redefine progressive bluegrass through his work with the Country Gentlemen, J.D. Crowe & the New South, and Emmylou Harris’ Hot Band. He launched his solo career in the early 1980s and became a leading figure in the neotraditional country movement. His string of #1 hits — including “Crying My Heart Out Over You,” “Highway 40 Blues,” and “Heartbroke” — made him one of the decade’s most influential artists. During this period he earned multiple CMA Awards, including Entertainer of the Year in 1985, as well as several Grammy Awards.

In the 1990s, Skaggs returned his focus to bluegrass, forming his acclaimed band Kentucky Thunder. In 2018, Skaggs was inducted into both the Country Music Hall of Fame and the Bluegrass Music Hall of Fame—one of the few artists to receive both honors. He is also a member of the Grand Ole Opry.

Skaggs has performed and recorded with a wide range of legendary artists across many genres, including Jack White, Ray Charles, Johnny Cash, Dolly Parton, Charlie Haden, Bruce Hornsby, Béla Fleck, John Fogerty, and Dionne Warwick, among many others.

Across his decades-long career, Ricky Skaggs’ contributions as a singer, mandolinist, fiddler, bandleader, and tradition-bearer have secured his legacy as one of the most important figures in American roots music.

Ricky Skaggs and Kentucky Thunder will present a special Christmas concert at the Brown County Music Center on December 11.