10 Of The Greatest And Most Famous Country Singers From Kentucky

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Written by Laura Macmillan
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Kentucky is well known for its horses, bourbon, southern hospitality and bluegrass. It’s no surprise then that many famous country music stars were born and raised in the Bluegrass State.

Kentucky borders Tennessee to the north, so the drive to Nashville for stardom was a short one for these now-famous locals. 

From Loretta Lynn helping build the origins of country music to Chris Stapleton leading the way into the new frontier of country sounds, Kentucky has an important place in the hearts of many country music lovers. 

In this post, we’re going to take a look at the lives and careers of 10 of the greatest and most famous country singers from Kentucky. Let’s get started.

1. Loretta Lynn

Up first, we have the most awarded female country artist, Loretta Lynn. She was born in Butcher Hollow, Kentucky, in 1932. Her career started in the late 1950s, but her breakthrough came in 1967 with her first #1 hit, “Don’t Come Home A-Drinkin’ (With Lovin’ on Your Mind).”

From then on, in a career that spanned more than sixty years, she performed as a country music singer and produced more popular songs, like “You Ain’t Woman Enough (To Take My Man)” and “Coal Miner’s Daughter.”

For her contribution to the genre, Lynn has been nominated for a Grammy award an astounding eighteen times—of which she won three awards.

Next: Read our list of amazing country artists here.

2. Chris Stapleton

Next, we have country star Christopher Stapleton, who was born in Lexington, Kentucky, and spent most of his childhood in Staffordsville. In 2001, he began studying at Vanderbilt University in Nashville, but soon dropped out to pursue music full time.

Stapleton is a prolific songwriter with more than 170 writing credits, including famous country hits like Kenny Chesney’s “Never Wanted Nothing More” and Luke Bryan’s “Drink a Beer.”

Before branching out as a solo artist, Stapleton sang with the bluegrass folk band the Steeldrivers, who still perform, tour, and produce music.

In the past ten years, Stapleton has won three Grammy awards as a solo artist and was named Songwriter of the Decade in 2019 by the American Country Music Awards.

3. Dwight Yoakam

Born in Pikeville, Kentucky, in 1956, Dwight Yoakam was exposed to music at a young age, as his family enjoyed listening to records and the radio, often singing along. He was also a talented guitarist and joined in his high school band, sometimes performing in local private parties.

His break came when he moved to Los Angeles and released his debut album, Guitars, Cadillacs, Etc., Etc. Since then, he has released more than twenty records and has sold more than 30 million records. He’s often credited with developing the term “hillbilly music,” and its signature rockabilly style is what he is most known for producing.

With this popular style, Yoakam has won two Grammy awards, and in 2019, he was inducted into the Nashville Songwriters Hall of Fame.

4. Keith Whitley

Born in Bedford, Keith Whitley first started performing in a bluegrass band in the early 1970s. He later moved to Nashville, Tennessee, and in 1988, Whitley released some of his most famous songs, including “Don’t Close Your Eyes” and “When You Say Nothing at All.”

However, just as his career was beginning to take off, sadly, Whitely passed away at the young age of thirty-four from alcohol poisoning.

Though his career was short-lived, Whitely’s contributions to the genre lives on—he has recently been inducted into the Country Music Hall of Fame.

5. Patty Loveless

Patricia Lee Ramey, better known by her stage name Patty Loveless, was born in Pikeville, Kentucky. She began singing at a young age, performing with her brother at local events.

Her career had a rocky start in 1985, with releases not reaching top 40, but by 1988, she had become a member of the Grand Ole Opry and began rising in popularity from there.

During her career in country music, she had five #1 singles and sold more than fifteen million records globally. Some of her most popular tracks include “Blame It on Your Heart” and “Lonely Too Long.”

Loveless has won two Grammy awards, the most recent in 2011 for Best Bluegrass album, and has been inducted into the Kentucky Music Hall of Fame.

6. Billy Ray Cyrus

Next, we have country legend Billy Ray Cyrus, who was born in Flatwoods, Kentucky. Cyrus developed a love for singing as a child since he was exposed to both bluegrass and gospel music by his community.

Over the years, he has released sixteen studio albums, but he is probably best known for his song “Achy Breaky Heart” and his verse in “Old Town Road” with Lil Nas X. Cyrus has won two Grammy awards, both in conjunction with “Old Town Road.”

He is also the biological father of pop singer Miley Cyrus. He and Miley starred in the hit Disney Channel show Hannah Montana. Since then, he has also appeared in various television series.

7. John Michael Montgomery

Born in Danville, Kentucky, country singer John Michael Montgomery spent his childhood in Nicholasville, Kentucky.

As a youth, Montgomery sang and played music with his brother, Eddie, who himself saw success as a member of the country music group Montgomery Gentry. 

Montgomery began his solo career in 1992 with his debut album Life’s a Dance. It only peaked at #4, but this was followed by a succession of #1 hits in the years after: “I Love the Way You Love Me,” “Be My Baby Tonight,” and “Sold (The Grundy County Auction Incident).”

He went on to release ten albums throughout his career.

8. Wynonna Judd

Our next singer’s journey with music began when she received a guitar for Christmas one year and learned how to play it. Ashland native Wynonna Judd then began her music career as a member of the county music duo the Judds, alongside her mother.

In the late 1970s, Judd and her mother moved to Nashville, Tennessee, where they saw significant success. Specifically, the Judds had 14 number-one hits. 

In her solo endeavors, Judd released about twelve albums with songs like  “I Saw the Light” and “No One Else on Earth.” In 2022, Judd and her mother—as the duo the Judds—will be added to the Country Music Hall of Fame.

9. Sturgill Simpson 

Our penultimate singer was born in Jackson, Kentucky. John Sturgill Simpson is better known by his middle name, Sturgill, which was his grandmother’s maiden name. He did a short stint in the navy before beginning his music career in 2004.

For him, it was a rocky start, but Sturgill eventually became known for his Americana-folk music with a distinctive county music flair, which has become very popular. His album Metamodern Sounds in Country Music was listed on Rolling Stone‘s 50 Best Albums of 2014 list and was nominated for a Grammy award.

Simpson has continued to produce and release music, with a new album dropping in 2022.

10. Ricky Skaggs

And last but by no means least, we have country and bluegrass singer Ricky Skaggs. He’s also a multi-instrumentalist who plays the mandolin, fiddle, guitar, and banjo.

Born in Cordell, Kentucky, Skaggs began playing music at a very early age, and his first public performance occurred when he was only seven years old. 

His solo career began in 1975 with the release of That’s It!, but his popularity skyrocketed after performing with singer-songwriter Emmylou Harris in 1977. His neotraditional style soon got him inducted into the Grand Ole Opry in 1982.

From 1983 to 2016, Skaggs has won 14 Grammy awards and been recognized by various other awards and accolades by the Country Music Association, Academy of Country Music, and International Bluegrass Music Association, to name some. 

Summing Up Our List Of Kentucky-Born Country Music Singers

As you can see, Kentucky is the home of a lot of country music talent. From legends like Ricky Skaggs to Sturgill Stimpson, the state has deep roots in bluegrass and country music.

However, this list barely scratches the surface, and there are many more amazing country singers hailing from Kentucky.

Who did we miss off our list? Let us know, and we’ll add them in!

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Laura has over 12 years experience teaching both classical and jazz saxophone and clarinet. She now resides in California where she works as a session and live performer.