And although he was too young to even try out, he just might have been ready.
Skaggs' lifelong dream to join the Grand Old Opry came true later in life, in 1982, followed by the impressive title of Entertainer of the Year in 1985.
He stopped by the The Early Show's "Second Cup Café" Saturday to perform songs from his lastest album, "The High Notes."
The Kentucky-born Skaggs wears a lot of hats as a musician, producer and composer, and he plays fiddle, guitar, banjo and mandolin.
As a teen, he teamed with fiddler Keith Whitley (also a teen). They hit it off and started playing together with Whitley's banjoist brother, Dwight, on radio shows.
With some hard work, they earned a spot opening for Ralph Stanley, then joined Stanley's band, the Clinch Mountain Boys. Their new gig led to live performances and recordings with J.D. Crowe & The New South.
After doing well with bluegrass, Skaggs headed toward country music, and was again a success. Country music garnered him eight awards from the Country Music Association (CMA).
Down the road, Skaggs decided to star his own record label, Skaggs Family Records, which has lead to collaborations with the Dixie Chicks, Travis Tritt, Joan Osborne and Bruce Hornsby.