Ricky Skaggs
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The 10 Best Ricky Skaggs Songs, Ranked

Ricky Skaggs' ongoing Hall of Fame career took him from his old Kentucky home to some of bluegrass and country music's biggest stages. From there, he became a mainstream traditionalist in the truest sense, expanding his country song arsenal without shunning his roots. Although Skaggs and his band Kentucky Thunder eventually returned to the bluegrass and gospel worlds, his legendary status in Nashville's country music circles never waned.

Like Marty Stuart, Alison Krauss, and numerous others, the Skaggs family truly raised Ricky on bluegrass. He and fellow Kentucky native Keith Whitley joined Ralph Stanley's Clinch Mountain Boys at a very young age. Together, they went from riding the wave of Deliverance popularity that also reinvigorated the career of Earl Scruggs. These experiences as a young bluegrass picker set a solid ground for a very bright future as a country artist.

Such beginnings didn't necessarily fit the country star mold in the cosmopolitan '80s. As the voice of a simple life of common country folks, Skaggs was perhaps a less likely star than George Strait, Randy Travis, or any other contemporary hit-maker with his roots on his sleeve. But he still managed to reach popularity on the billboards and become a Grammy-winning artist. 

Most of the following picks point to Skaggs' run as a mainstream country star in the 1980s. It's the time frame that made him a household name, marked by pop-accessible hits that embraced bluegrass style. The list easily could've focused more on his more recent return to bluegrass ("Sally Jo," "Get Up John"), collaborations with the likes of Bruce Hornsby (they cover Rick James' "Super Freak," of all things, and a cut fun take on "Cluck Ol Hen") or interpretations of old classics ("A Lonesome Night," "San Antonio Rose," "Little Cabin Home on the Hill," "Little Georgia Rose," "Black Eyed Suzie," "Wheel Hoss," "Toy Heart" and "Sweet Temptation" could be a list unto itself). All eras of Ricky Skaggs songs offered up top 10-worthy material, so keep in mind that this list barely scrapes the surface of his contributions to country and bluegrass music.

10. "Tennessee Stud"

Instead of just glossing over Skaggs' more recent contributions, it's worth focusing a little on this nod to the great Doc Watson. It demonstrates how Skaggs uses his platform to point to country music's roots.

9. "Hillbilly Highway"

Skaggs covered this Steve Earle composition about unapologetic Southernness and the simple life for the 1997 album Life is a Journey. It's the same overlooked disc that brought us the song "Lonesome Dove."

8. "Heartbreak Hurricane"

Lyrics and stories that could've been hits for other stars get played at a lightning-fast pace by Skaggs, as evidenced by this late '80s cut from the Kentucky Thunder album. You'll be heartbroke by the end of this one. 

7. "Love Can't Ever Get Better Than This"

Skaggs shines as a duet partner, both in this example co-starring Sharon White and at other times in his career. It's worth mentioning here that the Whites are family for Skaggs. He has been married to Sharon since 1981.

6. "I Wouldn't Change You If I Could"

This weepy guitar and fiddle-driven hit from Skaggs' country heyday is perhaps the sweetest love song in his massive back catalog.

5. "You've Got a Lover"

The best Skaggs cut grounded more in classic country storytelling than bluegrass picking remains this 1983 classic.

4. "Highway 40 Blues"

Honky tonk music meets front porch picking on this chart-topping story about life on the road. The blues sets in when the narrator realizes that the perks of stardom are things "a country boy can't use."

3. "Don't Cheat in Our Hometown"


From an earlier cut featuring Whitley to the countrified version that's the title track of a hit solo album, this Skagg classic adds the classic country theme of infidelity to the less secular bluegrass world.

2. "Cajun Moon"

A highlight of Skaggs' Live in London album, he adds some Louisiana flavor to this cross between a country hit and a bluegrass breakdown. It's from the same set of songs that brought us a great live recording of "I've Got a New Heartache."

1. "Country Boy"

In Skaggs' hands, this co-write by fellow Hot Band alum Albert Lee bridged the then-narrow gap between the audiences of Skaggs' bluegrass mentors (including the music video's "Uncle Pen," Bill Monroe) and his country star contemporaries.

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