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Drifting Cowboy

Drifting Cowboy

Ricky Skaggs Reveals What Keith Whitley Was Really Like

Oct 20, 2026 · 1h 8m

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About this episode

Country music legend and 15-time GRAMMY Award winner Ricky Skaggs joins the Drifting Cowboy Podcast for an unforgettable conversation about his extraordinary journey from a young Kentucky bluegrass prodigy to one of the biggest stars in country music—and his lifelong friendship with the late Keith Whitley. Ricky takes us all the way back to his childhood, when his father bought him his first mandolin for just $5 at the age of five. By six, he was sharing the stage with the Father of Bluegrass, Bill Monroe. At just seven years old, he appeared on television with Lester Flatt and Earl Scruggs on the Martha White Flour Hour, performing the bluegrass classic "Ruby." Ricky also opens up about…