Top 10 Ricky Skaggs Songs

Feature Photo: Steve Proctor, CC BY-SA 4.0 <https://creativecommons.org/licenses/by-sa/4.0>, via Wikimedia Commons

Originally born as Rickie Lee Skaggs in 1954 in Cordell, Kentucky, the artist known as Ricky Skaggs is a multi-talented artist that mixed bluegrass and neotraditional country music through his musical compositions and productions. In addition to his singing talent, Skaggs has also played banjo, fiddle, guitar, mandocaster, and mandolin. In 2016, he was inducted into the Musicians Hall of Fame and Museum and into the Country Music Hall of Fame in 2018. He was also awarded the National Medal of Arts in 2021, alongside fellow country musician Toby Keith.

In the Beginning

As a five-year-old, originally as Ricky Skaggs, he was given a mandolin by his father. By the age of six years old, he played and sang on stage with Bill Monroe. When he turned seven years old, he appeared on television, playing alongside with Lester Flatt and Earl Scruggs. At the time, he wanted to audition for the Grand Ole Opry, but he was told he was too young. Instead of letting that deter him, Skaggs continued to make an impression in the music industry.

When he met fellow guitarist Keith Whitley, the two teens began playing on radio shows, along with Whitley’s older brother, Dwight, who played the banjo. By 1970, the trio earned their place to join Ralph Stanley’s band, the Clinch Mountain Boys. Later, Skaggs joined The Country Gentlemen in Washington, D.C. In 1976, he formed a progressive bluegrass band called Boone Creek. This band included the members of Vince Gill and Jerry Douglas. Skaggs was also a member of Emmylou Harris’ Hot Band, even writing musical arrangements for her 1980 bluegrass album, Roses in the Snow.

Going Solo

In 1980, as Ricky Skaggs, he launched his solo career that saw him earn twelve number one hits, as well as a series of country music awards by the Country Music Association and the Academy of Country Music. In 1982, he finally became a member of the Grand Ole Opry, which also served as a record as he was the youngest musician ever to be inducted at that time. According to Chet Atkins, he credits Ricky Skaggs for saving country music from going into the entertainment industry abyss. Ricky Skaggs has been considered one of the leading pioneers of neotraditional country music. He made his debut via Epic Records in 1981 with Waitin for the Sun to Shine, which was instrumental to his chart introduction to both the country music charts and the pop charts due to his unique style.

This led to his 1982 album, Highways & Heartaches, which became his only RIAA-platinum certified album to date. For over a decade, Ricky Skaggs was among the most prolific neotraditional country music artists in the business. In 1996, he opted to return to his bluegrass roots and began to experiment with new sounds. He founded the band, Kentucky Thunder, and since the genre switch earned a Grammy Award for Best Bluegrass Album. He also won this with the Bluegrass Music Association.

#10 – I Wouldn’t Change You If I Could

Originally recorded by Jim Eanes in 1959, “I Wouldn’t Change You If I Could” inspired Ricky Skaggs to cover this song in 1983 as part of his track collection in Highways & Heartaches. For Skaggs, this became his fourth number one single on the US Billboard Hot Country Songs chart and it was also a number one hit on the RPM Canadian Country Classics chart. Arthur Q. Smith supposedly sold his written song to Jim Eanes, as he has sold him many in the past, but when Ricky Skaggs turned this into a hit singles and Eanes got the full credit, it was revealed half of its rights still belonged to the original songwriter. This resulted in the credit stripped away from Eanes as he had no proof of the sale and put into Smith’s name instead.

#9 – Uncle Pen

Originally written and recorded by Bill Monroe, “Uncle Pen” has since seen many cover versions, including the 1984 recording of Ricky Skaggs. It became another number one hit on the US Billboard Hot Country Songs chart and the RPM Canadian Country Tracks chart for the artist. The direct reference to “Uncle Pen” was also featured in the 1985 music video of “Country Boy” as he, along with Bill Monroe for that single, performed together. In the music video, Bill Monroe is referred to as “Uncle Pen.” Fast and fun, “Uncle Pen” continues to serve as an arm-swinging, toe-tapping classic that still remains a barn dance favorite.

#8 – Country Boy (featuring Bill Monroe)

“Country Boy” was the title track single that featured the legendary Bill Monroe. When this single was released in 1985, it quickly became yet another number one hit for Ricky Skaggs on the US Billboard Hot Country Songs chart. it also peaked at number one on the RPM Canadian Country Tracks chart. The music video for this hit was filmed in New York City as the narrator finishing a phone conversation with his uncle, who is played by Bill Monroe. This country-boy-at-heart performance between the two artists earned Ricky Skaggs an Entertainer of the Year win at the 1985 Country Music Association Awards.

#7 – Highway 40 Blues

This instrumental heavy country hit has been credited as the leading reason that made Highways & Heartaches the best-selling album to Ricky Skaggs’ credit since its 1982 release. On the US Billboard Hot Country Songs chart and the RPM Canadian Country Tracks chart, “Highway 40 Blues” peaked at number one in 1983. For Ricky Skaggs, this was the fifth time he enjoyed a number one single from his discographic resume, which stayed in the charts for a total of twelve weeks. Fans of the song who know the truth behind the lyrical tale know its not about the infamous Interstate 40 that runs through Nashville, Tennessee. It’s about the little state highway that’s situated in the state of Kentucky.

#6 – Singing as We Rise (featuring Gibson Brothers)

In 2012, Ricky Skaggs and the Gibson Brothers earned the 2012 Gospel Recorded Performance of the Year with the International Bluegrass Music Association (IBMA) Awards. This gospel-themed piece of inspirational music saw bluegrass Christianity at its finest as the collaboration between these two artists brought about a sense of revival to a community that soaked up what has since become a favorite among fans. “Singing as We Rise” was intentionally written as an old-style country classic that had deep bluegrass roots embedded into it that reflected upon the life of a God-loving, God-fearing family living in a world that sometimes seems a bit too complex for its own good.

#5 – Sacred Memories (featuring Joe Mullins & the Radio Ramblers and Sharon White Skaggs)

During the 2017 International Bluegrass Music Association (IBMA) Awards ceremony, Ricky Skaggs and his wife, Sharon White Skaggs, earned the win for Gospel Recorded Performance of the Year for “Sacred Memories,” a recording they collaborated with Joe Mullins & the Radio Ramblers. The 2016 album was also titled Sacred Memories, which ultimately served as a bluegrass Christian album that dug into the roots of everyday culture according to the life of a bible-believing Jesus-follower. Cheerily, “Sacred Memories” brought up memories of old songs and traditional beliefs that still remain prominent among strong bible-believing Christians.

#4 – A Simple Life (featuring Kentucky Thunder)

“A Simple Life” won a 2003 Grammy Award for Best Country Performance By A Duo or Group With Vocal. Working with his band, Kentucky Thunder, the return to bluegrass musical roots paid off with this single. As a group, Kentucky Thunder featured Ricky Skaggs and his wife, Sharon White Skaggs. As a group, Ricky served as the lead vocalist and mandolin player. As a group, they’ve won Instrumental Group of the Year many times over with the International Bluegrass Music Association. In addition to the Grammy won for “A Simple Life,” there were six additional Grammy Awards the group has so far earned.

# 3 – Cajun Moon

Continuing with our top 10 Ricky Skaggs songs list we takes a heartfelt listen to the fantastic number entitled “Cajun Moon.” The song was released on the album called Live In London. This was a big release for Ricky Skaggs. With the song “Cajun Moon,” Ricky Skaggs celebrated his tenth number one hit on the US Billboard Country Music charts. The songs was composed by Jim Rushing. It was released in 1986.

#2 – Restless (featuring Mark O’Connor, Vince Gill and Steve Wariner)

In 1991, “Restless” won a Grammy Award for Best Country Vocal Collaboration for Ricky Skaggs, Mark O’Connor, Vince Gill, and Steve Wariner. This 1968 Carl Perkins classic peaked at number twenty-five for the trio in 1990 on the US Billboard Hot Country Songs chart and at number nineteen on the RPM Canadian Country Tracks chart. Speedily, “Restless” played itself out as a fun-loving song that easily made it a barn-dancing classic.

#1 – Go Rest High on That Mountain (featuring Vince Gill and Patty Loveless)

Ricky Skaggs and Vince Gill shared their vocal talent for 1995’s “Go Rest High on That Mountain,” a hit single that won the Country Music Association’s Song of the Year Award. It was also one of the most performed songs in 1997. This eulogic ballad was written in memory of Keith Whitley, who died in 1989. The write-up of this song didn’t finish until 1993 when Vince Gill’s brother, Bob, died from a heart attack in 1993. Vince Gill sang the lead in this single that featured Ricky Skaggs and Patty Loveless singing in the background. Although the song didn’t name anybody in specific, it was meant as a lyrical performance to honor those who have died, leaving their loved ones behind to not necessarily mourn their passing, but honor their memory.