The Best Ricky Skaggs Songs: The Man Who Courageously Saved Country Music

In the early 1980s, Ricky Skaggs songs dominated the country radio. He polished his sound enough that he eventually turned into a mainstream country star and chart-topper. Since 1990, Skaggs has become a leader of the progressive bluegrass movement and one of the reigning legends.

Skaggs managed to build prominence for his uniqueness and the excitement he brought during live appearances and recordings. His popularity kept soaring, and he garnered dozens of awards and recognitions – including four Grammy Awards. But most importantly, Skaggs renewed strength and notoriety to a sound that had been to some extent overpowered by the commercialization of the ‘Urban Cowboy’ fad.

Truly, Ricky Skaggs‘ talent served him well. So, let’s take a walk down memory lane and enjoy his best hits.

1. Country Boy

What makes “Country Boy” stand out is that it features all the elements that make Skaggs’ music special – the long instrumental interludes that no other bluegrass artist can match. It also comes with an amusing music video wherein bluegrass pioneer Bill Monroe made an appearance.

2. Uncle Pen

“Uncle Pen” was written and first recorded by Bill Monroe, who is acknowledged as the “father of bluegrass music.” Eventually, it was covered by several artists, including Porter Wagoner, Goose Creek Symphony, and of course, Skaggs – who brought the song to the top of the country chart.

3. Highway 40 Blues

The fifth among his consecutive No. 1 hits, “Highway 40 Blues,” is a song that tells the tender story of a traveling musician. The man has roamed the highway for years and wasted his youth in his search for truth. Skaggs’ remarkable instrumental solo dominating the track makes the song even more special.

4. Honey (Open That Door)

“Honey (Open That Door)” was one of the best tunes written by prolific and top-tier country music singer-songwriter Mel Tillis. It was first recorded by country singer Webb Pierce – however, it failed to enter the country chart.

5. Heartbroke

Skaggs released the song as the first single off his 1982 studio album Highways & Heartaches. Two weeks later, George Strait released his version, not knowing Skaggs had recorded it. Still, it was Skaggs’ version that defined the song, reaching No. 1 on the country chart.

Skaggs’ changed one line in the song to exclude a curse word. He made sure he would never record any song that would make him uncomfortable singing in front of his parents.

6. Love Can’t Ever Get Better Than This

In this song, Skaggs joined forces with his wife, Sharon White, of the country music vocal group The Whites. Though it was just their first-ever duet, it scored a massive success. In addition to reaching No. 10 on the country chart, it also earned them a CMA Award for Vocal Duo of the Year.

7. Lovin’ Only Me

After three years of not having No. 1, Skaggs went back to the top of the country chart “Lovin’ Only Me.” While it sounded different from the rest of Skaggs’ hits, the song’s twangy guitars and mid-tempo groove totally stood out. It was his final No. 1 Billboard Hot Country Songs chart.

8. I Wouldn’t Change You If I Could

Previously recorded by Jim Eanes in 1959, the song achieved better success when Skaggs released it in 1983. In the song, Skaggs showed off how he handled mid-tempo, vocal-oriented material, and he did it perfectly.

9. Don’t Cheat in Our Hometown

Long before Skaggs recorded the song, he played it many times for his musician friends – including Kris Kristofferson, who reacted very positively. Skaggs thought that if someone as prolific as Kristofferson liked it, he should consider recording it.

Well, he did not only record it, but he also made it the title track of his album. 

10. Cajun Moon

When Skaggs first heard the song, he never saw it as a single. But his wife Sharon White insisted it was a hit – and she was right. “Cajun Moon” danced its way to the top of the country chart.

11. Something in My Heart

Released as the first single off his epic album Country Boy, “Something in My Heart” reached No. 2 on Billboard’s Hot Country Songs chart.

12. You’ve Got a Lover

Another country No. 2 for Skaggs, “You’ve Got a Lover” tells the painful story of a man whose heart has been broken knowing that his lover found a new man.

13. I Don’t Care

In 1982, Skaggs was on top of Billboard’s country chart for a dozen weeks with a cover of a Webb Pierce song. Skaggs has always been fond of the song for its simple yet straightforward lyrics of hope and promise.

14. Crying My Heart Out Over You

Skaggs turned into the catalog of one of the greatest bluegrass bands Flatt and Scruggs, covering “Crying My Heart Out Over You” in 1982. It became the first among Skaggs’ No. 1 hits.

15. I’ve Got a New Heartache

“I’ve Got a New Heartache” reached No. 2 on the country chart when country star Ray Price released it as the first single off his Greatest Hits compilation album in 1956. Three decades later, Skaggs brought the song back to the Top 10 with his version.

Here Are Some More Ricky Skaggs Songs That Stand Out From His Catalog

Without a doubt, None of Ricky Skaggs’ 1980s peers had better musical credentials than him. He’s an exceptional singer and instrumentalist that calling him multi-talented wouldn’t even be enough. Here are some more of his songs that truly stand out.

So, what are you waiting for? Get ready to play these Ricky Skaggs songs on repeat.