Top 5 Ricky Skaggs Songs

Ricky Skaggs is known as a country music trailblazer for integrating the niche nature of bluegrass into the mainstream country music scene. On Tuesday (July 18), he celebrated this triumphant feat and other life milestones with his 69th birthday.

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Born in the small town of Cordell, Kentucky, Skaggs grew up as a mandolin prodigy and by the age of six, was on stage playing with Bill “The Father of Bluegrass” Monroe. From then on, his career spread like wildfire, as the artist joined the Country Gentleman, then formed Boone Country alongside Vince Gill, and was later an integral member of Emmylou Harris’ Hot Band.

Subsequent to his early bluegrass stint, Skaggs became a bonafide country star with his 12 No. 1 hits, 8 CMA Awards, and 8 ACM Awards. Thanks to his savant-like talent and ornate career, Skaggs is often referred to as one of the founders of the Neo-traditional country music sub-genre. Additionally, Skaggs has been inducted into the Musicians Hall of Fame, and Country Music Hall of Fame, and was the recipient of the National Medal of Arts given to him by former President Trump.

So, without further ado, here are five of Skaggs’ most notable songs:

1. “I Wouldn’t Change You If I Could”

“I Wouldn’t Change You If I Could” was originally recorded in 1959 by Jim Eanes. Skaggs produced, recorded, released, and made the song notable in 1983. The tune made it to the No. 1 spot on the Billboard Hot Country chart. The song also scored Skaggs his fourth No. 1 hit. “I Wouldn’t Change You If I Could” is an affectionate country and bluegrass waltz that tells an endearing tale about the chemistry two lovers share. The song is bound to get stuck in the head of the listener due to its simple arrangements, catchy melodies, and spell-binding lyrics.

2. “Country Boy”

Written by British band Heads, Hands, & Feet, “Country Boy” was recorded by Skaggs in 1985 as the second single track of his album Country Boy. The song garnered Skaggs his ninth No. 1 country hit. Besides the single’s excellent use of storytelling and classical bluegrass techniques, it also has a memorable music video that includes cameos from Monroe, then-New York mayor Ed Koch, and actor David Keith.

3. “Uncle Pen”

Monroe initially wrote and recorded “Uncle Pen,” and it was later released by Skaggs in 1984 on his album I’m Head Over Heels in Love. Yet again, Skaggs made it to the No. 1 spot on the country charts. It’s a quintessential pop-bluegrass tune that one can’t help but dance to, thanks to its bullet-speed instrumentals and lyrics.

4. “Highway 40 Blues”

A classic highway ballad, “Highway 40 Blues” was written by Larry Cordle, and then released by Skaggs on the B-side of his 1983 album, Highways and Heartaches. The piece gave Skaggs his fifth No. 1 chart-topping song. The song is often viewed to be about Highway 40 which runs through Nashville, though, Cordle discloses that it’s actually about a state highway in Kentucky. The song conveys classic narrative tropes regarding the notorious highway ballad archetype. Furthermore, Skaggs masterfully proves that the steel guitar can in fact, also be used in bluegrass music.

5. “Cajun Moon”

“Cajun Moon” was originally written by Jim Rushing. Skaggs then produced and then released it in 1986 as the second single on his album Live In London. The track was Skaggs’ 10th No. 1 hit on the country charts. A classic country/folk tune that includes the fiddle, steel guitar, and harmonica, as well as a lyrical setting that embodies Southern love within the state of Louisiana.

(Photo by Terry Wyatt/Getty Images)

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