Ricky Skaggs’ first album on a major label, Sweet Temptation, came out in 1979. In the years since then, Skaggs put out plenty of hits, including these three. All released early in his career, they are so good that every country music fan should still know them today.
“Crying My Heart Out Over You”
His first No. 1 single, “Crying My Heart Out Over You” came out in 1981. The song, written by Lester Flatt, Earl Scruggs, Carl Butler, and Earl Sherry, was first recorded by Flatt & Scruggs in 1960.
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About 21 years later, Skaggs included “Crying My Heart Over You” on Waitin’ For The Sun To Shine, his second project on Sugar Hill Records.
The sad song says, “Now, I’m crying my heart out over you / Those blue eyes now they smile at someone new / Ever since you went away / I die a little more each day / ‘Cause I’m crying my heart out over you.”
In 1982, Skaggs earned a CMA Award nomination for Single of the Year for “Crying My Heart Out Over You”. The trophy that year went to Willie Nelson instead, for “Always On My Mind”.
“Country Boy”
One of Skaggs’s more popular singles, “Country Boy” came out in 1985. The title track of his seventh studio album, “Country Boy” was written by Tony Colton, Albert Lee, and Ray Smith.
What makes “Country Boy” stand out is the unique video, which shows Skaggs in New York City. Bluegrass pioneer Bill Monroe appears in the video. So does Ed Koch, who was the mayor of New York City at the time. Actor David Keith stars in the video as well.
A true anthem about the country way of life, “Country Boy” says, “Show me where I start / Find a horse and cart / I’m just a country boy / Country boy at heart.”
“Highway 40 Blues”
On Highways & Heartaches is “Highway 40 Blues”. The song, written by Larry Cordle, became Skaggs’s fifth consecutive song to land at the top of the charts.
“Highway 40 Blues” begins with “Well, these Highway Forty blues / I’ve walked holes in both my shoes / Counted the days since I’ve been gone / And I’d love to see the lights of home.”
Skaggs reportedly changed the lines, “My eyes are filled with bitter tears / Lord, I could use could an ice-cold beer” to “My eyes are filled with bitter tears / Lord, I ain’t been home in years.” He did so to not offend his deeply religious parents.
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