20 Country Singers Who Are From Kentucky

Ebet Roberts/Redferns, Michael Ochs Archives/Getty Images, C Flanigan/Getty Images

The state of Kentucky is nicknamed The Bluegrass State, so it makes sense that there is so much talent that comes from it!

Kentucky boasts a rich musical heritage that has left an indelible mark on the cultural landscape of the United States. From the hollers of Appalachia to the vibrant streets of Louisville, the state has been a cradle for many influential musicians across various genres.

Let’s take a look at the vast number of musicians that hail from The Bluegrass State!

Loretta Lynn

CIRCA 1975: Loretta Lynn performs onstage with a microphone circa 1975. (Photo by Michael Ochs Archives/Getty Images)

Born on April 14, 1932, to parents Clara Marie and Melvin Theodore “Ted” Webb, Loretta Lynn famously grew up in Butcher Holler, Kentucky. Her song “I’m A Honky Tonk Girl” really put her on the map and she was able to release other songs that solidified her legacy in country music. Her catalog includes 24 number-one songs and 11 number-one albums.

Her life story was made into the movie Coal Miner’s Daughter, which earned actress Sissy Spacek an Academy Award for Best Actress for her portrayal of Loretta. The two remained friends until Loretta’s passing in 2022.

Loretta’s legacy lives on in her songs, including “Coal Miner’s Daughter,” “YouAin’t Woman Enough (To Take My Man),” “Fist City,” “The Pill,” and so many more. She wrote over 160 songs in her lifetime and released 60 total albums. She has three Grammy Awards, 13 ACM Awards, eight CMA Awards, and 26 Music City News Awards (now called CMT Music Awards).

A proud Kentuckian, she was inducted into the Kentucky Music Hall of Fame in 2002. Sadly, Loretta passed away on October 4, 2022.

Crystal Gayle

Crystal Gayle with her American Music Award
Crystal Gayle / Facebook

Crystal Gayle also hails from Butcher Holler, Kentucky. That’s because she is Loretta Lynn’s younger sister! She was born Brenda Gail Webb and after being signed to Decca Records after graduation from high school, they asked her to change her first name because Brenda Lee was already signed with them and they didn’t want any confusion. And then, the name Crystal Gayle was born.

She is known for her signature song, “Don’t It Make Your Brown Eyes Blue.” After nearly 50 years in the business, she was finally inducted as a member of the Grand Ole Opry in 2017. She was inducted into the Kentucky Music Hall of Fame in 2008.

Peggy Sue

Peggy Sue album cover art
Peggy Sue Wright / Facebook

Did you know Loretta has two sisters who followed her lead into the country music world? That’s right, Peggy Sue is Loretta’s sister, and 11 years her junior, meaning she is also from Butcher Holler, Kentucky!

She had minor success in the genre in the late 1960s thanks to her songs “I’m Dynamite,” “All-American Husband,” and “I’m Gettin’ Tired of Babyin’ You.” Peggy Sue also helped write her sister’s song “Don’t Come Home A’ Drinkin’ (With Lovin’ on Your Mind).”

She continued having some success in the 80s and 1987, she began performing with her sister, Crystal Gayle, and still does to this day.

Keith Whitley

Keith Whitley performed at an RCA Records Convention at the Arrowood Hotel in Purchase, New York on August 4, 1988. (Photo by Ebet Roberts/Redferns)

Keith Whitley was born in Ashland, Kentucky on July 1, 1954, and raised in Sandy Hook, Kentucky. Taking from his state’s name, he began his career singing bluegrass and moved to Nashville in 1983 to pursue a country music career. Three years later, he released “Miami, My Amy,” which became his first Top 20 hit. He had a string of hits, including “Don’t Close Your Eyes,” “When You Say Nothing at All” and “I’m No Stranger to the Rain” until his untimely death in May 1989 at the age of 34.

His estate released several singles after his death, like “I Wonder Do You Think of Me,” “It Ain’t Nothin’,” and “I’m Over You.”

He was inducted into the Kentucky Music Hall of Fame in 2011.

Chris Stapleton

AUSTIN, TX – OCTOBER 02: Chris Stapleton performs during the 2016 Austin City Limits Music Festival at Zilker Park on October 2, 2016 in Austin, Texas. (Photo by C Flanigan/Getty Images)

Chris Stapleton was born on April 15, 1978, in Lexington, Kentucky, and grew up in Staffordsville, Kentucky. He moved to Nashville in 2001 and began writing songs for other artists before joining the band, The SteelDrivers. In 2015, he released his album Traveller, and his performance of “Tennessee Whiskey” and “Drink You Down” with Justin Timberlake at the CMA Awards put him on the map.

He now has five solo albums, all of which have topped Billboard‘s Top Country Albums chart. Stapleton has not been inducted into the Kentucky Music Hall of Fame…yet! But with 10 Grammy Awards, 10 ACM Awards, 14 CMA Awards, and many more, we’re sure his time will come sooner rather than later.

Patty Loveless

AUSTIN, TX – JUNE 18: Patty Loveless performs during the 2015 Austin City Limits Hall of Fame Induction and Concert at ACL Live on June 18, 2015 in Austin, Texas. (Photo by Gary Miller/Getty Images)

Patty Loveless was born in Pikeville, Kentucky, and like her distant cousin Loretta Lynn, she, too, was a coal miner’s daughter. Because her dad was a coal miner, he developed black lung disease, and the family relocated to Elkhorn City, Kentucky so her father could receive treatment.

She was discovered by The Wilburn Brothers when she was just 11 years old and after she graduated high school, she joined them as their backup singer on the road. In the mid-80s she was inspired by neo-traditional artists such as Randy Travis, Dwight Yoakam, and The Judds, and moved to Nashville.

She has released 16 albums, 11 compilation albums, two video albums, and 52 singles in her illustrious career. Some of her hits include, “Timber, I’m Falling in Love,” “Chains,” “Blame It on Your Heart,” “Lonely Too Long,” and so many more!

Loveless was inducted into the Kentucky Music Hall of Fame in 2011.

Billy Ray Cyrus

BUENA PARK, CA – JULY 24: Country Singer Billy Ray Cyrus attends “The Movieland Wax Museum Induction of Wax Figure of Billy Ray Cyrus” on July 24, 1993 at Movieland Wax Museum in Buena Park, California. (Photo by Ron Galella, Ltd/Ron Galella Collection via Getty Images)

Billy Ray Cyrus grew up in Flatwoods, Kentucky, and is known for his breakout song “Achy Breaky Heart.” Despite people calling him a one-hit wonder, Cyrus has released 16 studio albums and 53 singles since 1992.

He starred alongside his daughter, Miley Cyrus, on the hit Disney show Hannah Montana from 2006-2011. In 2019, Cyrus appeared on the remix of Lil Nas X’s song “Old Town Road,”  and it spent a record-breaking 19 weeks at #1. The song won Cyrus his first two Grammy Awards. He was inducted into the Kentucky Hall of Fame in 2018.

Dwight Yoakam

NASHVILLE, TN – SEPTEMBER 21: Dwight Yoakam performs at Ryman Auditorium on September 21, 2016 in Nashville, Tennessee. (Photo by Erika Goldring/WireImage)

Dwight Yoakam made a name for himself when his first three albums, Guitars, Cadillacs, Etc., Etc.Hillbilly Deluxe, and Buenas Noches from a Lonely Room, all reached the number one spot on the Top Country Albums chart. His accolades include two Grammy Awards and one Academy of Country Music award. His 1993 album, This Time, is certified triple-platinum!

Yoakam was born in Pikeville, Kentucky, and lived there until his family moved to Columbus, Ohio when his dad was discharged from the army. He was inducted into the Kentucky Music Hall Of Fame in 2008.

Tyler Childers

Photo of Tyler Childers
Tyler Childers / Facebook

Tyler Childers is a singer-songwriter who mashes up the genres of neotraditional country, bluegrass, and folk. To date, he has released six studio albums as well as six EPs. His breakout album, Purgatory, was released in 2017.

In 2018, he won Emerging Artist of the Year at the Americana Music Honors & Awards and has been nominated for seven Grammy Awards.

Naomi Judd & Wynonna Judd

Wynonna and Naomi Judd of the country music duo The Judds are shown performing on stage during a “live” concert appearance on April 12, 1991. (Photo by John Atashian/Getty Images)

The late Naomi Judd was born in Ashland, Kentucky. She is best known as part of the mother-daughter duo The Judds, alongside her eldest daughter, Wynonna Judd.  Together, they earned 15 number-one hits, with five others making it to the Top Ten on the charts.

For eight consecutive years, The Judds won the Vocal Duo award at all three major country music awards shows. They won five Grammy Awards together and Naomi won a Grammy for writing “Love Can Build a Bridge,” which coincidentally became the last song she ever performed live at the 2022 CMT Music Awards.

Wynonna had a successful solo career as well, with hits like “No One Else on Earth.”

Naomi passed away from a self-inflicted gunshot wound just days before she was set to be inducted into the Country Music Hall of Fame. Naomi and Wynonna were inducted into the Kentucky Hall of Fame in 2006. 

Ricky Skaggs

Photo of Ricky Skaggs
Ricky Skaggs / Facebook

Born in Cordell, Kentucky, Ricky Skaggs first started playing music at the young age of 5! He started his career in various bluegrass bands with Keith Whitley, Vince Gill, and Emmylou Harris, among others!  Skaggs launched a solo career in 1980 and has since had 12 number-one hits, eight CMA awards, and eight ACM awards. He has also won 15 Grammy Awards!

In 2004, he was inducted into the Kentucky Music Hall of Fame.

Bill Monroe

Photo of bill Monroe performing "Wayfaring Stranger"
vintage18lover / YouTube

It’s no shock that the “Father of Bluegrass” hails from Kentucky. Rosine, Kentucky, to be exact. Bill Monroe is credited as the creator of bluegrass music, so he might be the most fitting person on this list!

Bill created several bands including, Monroe Brothers, Kentuckians, and his most famous band, the Blue Grass Boys. He had a decades-long career that earned him a spot in the Kentucky Music Hall Of Fame in 2002, which was the first year they inducted anyone.

The legend passed away on September 9, 1996, at the age of 84.

Carly Pearce

Carly Pearce at The 57th Annual CMA Awards at Bridgestone Arena in Nashville, Tennessee on November 8, 2023. (Photo by Christopher Polk/Variety via Getty Images)

Hailing from Taylor Mill, Kentucky, Carly Pearce had a music breakthrough in 2017 when her single “Every Little Thing” topped the charts. Since her debut, she has released three albums, with one more coming in June 2024.

Pearce won three CMA Awards, four ACM Awards, a CMT Music Award, and a Grammy Award, and she became a member of Grand Ole Opry in 2021.

The Kentucky Music Hall of Fame inducted her in 2022.

Sturgill Simpson

Photo of Sturgill Simpson
Sturgill Simpson / Facebook

Sturgill Simpson hails from Jackson, Kentucky. He broke out in 2013 when he self-released his debut album. He won a Grammy for Best Country Album in 2017 and has also taken home two Americana Music Awards.

John Michael Montgomery

NASHVILLE, TN – JUNE 12: John Michael Montgomery performs on the Honky Tonkin with Tracy Lawrence show during the CMA Festival at the Ascend Stage on June 12, 2016 in Nashville, Tennessee. (Photo by Beth Gwinn/Getty Images)

John Michael Montgomery began his career in 1992, and has had seven number-one hits: “I Love the Way You Love Me,” “I Swear,” “Be My Baby Tonight,” “If You’ve Got Love,” “I Can Love You Like That,” “Sold (The Grundy County Auction Incident)” and “The Little Girl.”

He was born in Danville, Kentucky, and raised in Nicholasville, Kentucky, along with his brother, Montgomery Gentry’s Eddie Gentry.

Montgomery was inducted into the Kentucky Music Hall of Fame in 2011.

Justin Holmes

Country Rebel

Justin Holmes is a country singer who hails from Paduka, Kentucky. He always had a love for country music and when he joined the Air Force at 18, he played for his fellow service members and had dreams of one day playing music professionally.

He made waves in 2017 when he went viral for his cover of George Jones’ “The Grand Tour” and fellow Kentuckian Keith Whitley’s “Don’t Close Your Eyes,” and years later, signed with Country Rebel Records and released his debut single, “Drink You Down.”

On Friday, April 12, Holmes released his second single, “Heartbreak Honky Tonk.” When debuting the music video, Holmes said, “I wrote this song after stumbling upon a lick on my guitar. It just felt 90’s country and it got me thinking about honky tonks, sawdust floors, and heartbreak. This is one of those songs that kind of just wrote itself and I’m very proud of the work we all put into making what I heard in my head come to life!”

Singer Jessie G and her real-life husband, Matt, star in the accompanying music video, which you can watch below.

YouTube video

Montgomery Gentry’s Troy Gentry & Eddie Montgomery

No photo description available.

Just like his Montgomery Gentry brother Eddie Montgomery, Troy Gentry also called Kentucky, home. The duo formed in 1999 and released six studio albums in their time together. their hit songs include “Folks Like Us,” “If You Ever Stop Loving Me,” “Something to Be Proud Of,” “Lucky Man,” “Back When I Knew It All,” “Gone,” “My Town,” and many, many more!

Montgomery Gentry was inducted into the Kentucky Music Hall of Fame in 2015. Sadly, Troy Gentry passed away on September 8, 2017 just hours before a performance in a helicopter crash.

Grandpa Jones

Grandpa Jones
Country Road TV / Facebook

Louis Marshall Jones was born on October 20, 1913, he later went professionally by “Grandpa Jones.” He was known for his impressive banjo skills and his country and gospel music. Grandpa Jones began performing at the Grand Ole Opry in 1946. He was a cast member on the show Hee Haw, and inducted into the Country Music Hall of Fame in 1978. Jones was among the first inductees into the Country Music Hall of Fame in 2002.

Jones passed away on February 19, 1998 after suffering two strokes the month prior.


Photo of Stringbean
Country Music Hall of Fame and Museum / Contributor / Getty Images

David Akeman, better known as “Stringbean,” became well known thanks to his time on the show Hee Haw.

Sadly, Stringbean and his wife were murdered in 1973 as they returned home from a performance at the Grand Ole Opry. Their neighbor, friend, cast mate, and fellow Kentuckian Grandpa Jones found them. Their deaths rocked the country music world.

Stringbean was inducted into the Kentucky Music Hall of Fame in 2018.

Did you know about all these singers who are from Kentucky? Let us know who we missed in the comments! 

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