10 Of The Greatest And Most Famous Country Singers From Kentucky

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 Loretta Lynn who was born in Butcher Hollow, Kentucky in 1932.

In a career that spanned more than sixty years, she performed as a country music singer and produced popular songs like “You Ain’t Woman Enough (To Take My Man)” and “Coal Miner’s Daughter” earning twenty-four number-one hit singles. 

She has been nominated for a Grammy award an astounding eighteen times–of which she won three awards.

She also won a Grammy with another county music notable, Conway Twitty, who she sang with often.

2. Chris Stapleton

Next, we have country star Christopher Stapleton who was born in Lexington, Kentucky, and spent most of his childhood in Staffordsville, Kentucky.

In 2001, Stapleton moved to Nashville, Tennessee, to begin college at Vanderbilt University 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 by the American Country Music Awards. 

3. Dwight Yoakam

Dwight Yoakam was born in Pikeville, Kentucky, in 1956. Throughout his youth, Yoakam participated in his high school drama performances and played his guitar.

Since then, he has released more than twenty records and has sold more than thirty 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.

In addition to his music career, Yoakam has also appeared in many movies like Sling Blade and Four Christmases. 

4. Keith Whitley

Keith Whitley was born in Bedford, Kentucky, and grew up near Sandy Hook, Kentucky.

He first started performing in a bluegrass band in the early 1970s. About a decade later, he 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.”

But just as his career was beginning to take off, sadly, Whitely died young at the age of only thirty-four.

But, to celebrate his short but important contribution to the genre, in 2022, he was posthumously 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 spending her childhood in Elkhorn City, Kentucky, and Louisville, Kentucky.

During her career in country music, she had five number-one singles, and she sold more than fifteen million records globally. 

Some of her most popular tracks include “Blame It on Your Heart” and “Lonely Too Long.” L

Loveless is a Grand Ole Opry member and has been inducted into the Kentucky Music Hall of Fame. She won two Grammy awards, the most recent in 2011 for Best Bluegrass album. 

6. Billy Ray Cyrus

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

Over the years, Cyrus 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 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 and, during that time, released such songs as “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

Born in Ashland, Kentucky, Wynonna Judd began her music career as a member of the county music duo, The Judds, alongside her mother.

Her journey with music began when she received a guitar for Christmas one year and learned how to play it.

In the late 1970s, Judd and her mother moved to Nashville, Tennessee, where they saw significant success. Specifically, The Judds had fourteen 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 

Born in Jackson, Kentucky, and attending Woodford County High School near Versailles, 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.

He’s 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” 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

Andk last but by no means least, we have Ricky Skaggs, who is a country and bluegrass singer. 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. 

He met fellow Kentuckian Keith Whitley when he was a teen, and they struck up a musical friendship. Skaggs is also connected with other notable musicians, including Earl Skaggs, Emmylou Harris, and Vince Gill.

From 1983 to 2016, Skaggs was nominated for or won a Grammy award. He’s been recognized by various other awards and accolades throughout the years. 

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 outlaws like Sturgill Stimpson, the state has deep roots in bluegrass and country music.

But, 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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Written by Laura Macmillan
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.