Kentucky is a fascinating place, full of natural resources, caves, and twists and turns through a bucolic country. Though it is known as “The Bluegrass State” for its ubiquitous type of grass, the genre of bluegrass music was also invented here. Indeed, out of the Kentucky mountain hollers, many great musical acts have sprung forth. Let’s meet the 10 biggest musicians from Kentucky. (Discover the top 50 songs about America.)
To compile a list of the 10 biggest musicians from Kentucky, 24/7 Tempo consulted various musical sites and databases including Hello Music Theory and The Singers Room. Next, we selected musicians from a range of genres and decades. After that, we consulted sites like Biography and Britannica for the musicians’ biographical information.
Loretta Lynn
- Hometown: Butcher Hollow
One of the biggest musicians from Kentucky is Loretta Lynn. She first got started in music playing in local clubs before she was spotted by a representative from Zero Records. This led to a widely successful music career, spawning numerous hit songs like “Coal Miner’s Daughter” and “I’m a Honky Tonk Girl,” as well as the musical film “Coal Miner’s Daughter” based on her life.
Known for her groundbreaking role in country music, Lynn received many accolades for her work. Besides awards from the Country Music Association and the Academy of Country Music, Lynn was nominated for 18 Grammy Awards, winning three. As of 2022, Lynn is history’s most-awarded female country music artist. She died of natural causes the same year.
Billy Ray Cyrus
- Hometown: Flatwoods
Billy Ray Cyrus is a country singer, songwriter, and actor. He first rose to prominence with his hit song, “Achy Breaky Heart. This song not only topped the country charts, it achieved triple-platinum status in Australia, as well as repopularizing the line dance. Since then, Cyrus has had a prolific career, recording 16 studio albums featuring over 50 hit songs.
Though Cyrus continued to hit platinum with his releases, he earned his first number-one single in 2019 after appearing on Lil Nas X’s song “Old Town Road.” In addition to music, Cyrus has also had a successful acting career. His credits include “Mulholland Drive,” “The Nanny,” “Diagnosis Murder,” and “Love Boat.” Cyrus is the father of equally successful singer-songwriter Miley Cyrus.
Dwight Yoakam
- Hometown: Pikeville
Another one of the biggest musicians from Kentucky is Dwight Yoakam. Born Dwight David Yoakam, he first rose to prominence after releasing his debut album “Guitars, Cadillacs, Etc. Etc.” This album, along with the next two, all reached number one on the country charts. Yoakam has also had two number-one hit songs called “Streets of Bakersfield” and “I Sang Dixie.”
In addition to music, Yoakam is a successful and well-regarded actor. Some of his credits include “Sling Blade,” “Panic Room,” “Wedding Crashers,” and the television show “Under the Dome.” For his musical success, Yoakam has won two Grammy Awards and one Academy of Country Music Award.
Chris Stapleton
- Hometown: Lexington
Born Christopher Alvin Stapleton, Chris Stapleton is a singer-songwriter, guitarist, and producer. He first rose to prominence as a songwriter, co-writing six number-one country songs for other artists. After a successful behind-the-scenes career, Stapleton embarked on a solo career, with his first album “Traveller” reaching number one on the Billboard charts and being certified platinum four times over.
It’s no surprise then that Stapleton has received many accolades for his work. These include eight Grammy Awards, 14 Country Music Association Awards, and 10 Academy of Country Music Awards. Moreover, The Academy of Country Music named him the artist-songwriter of the decade in 2019.
Jim James
- Hometown: Louisville
Born James Edward Olliges Jr., Jim James is a songwriter, guitarist, singer, and producer. He first rose to prominence as frontman for the successful indie rock band My Morning Jacket. With the band, James has released several critically acclaimed albums including “It Still Move,” and “Z”.
In addition to My Morning Jacket, James embarked on a notable solo career releasing seven studio albums. Also known for his collaboration, James has contributed vocals to tracks by bands like Calexico and The Decemberists. Besides music, he also played the role of band leader in the Bob Dylan biopic film, “I’m Not There.”
The Kentucky HeadHunters
- Hometown: Edmonton
The Kentucky Headhunters are a country and Southern rock band. They first rose to prominence with the release of their debut album, “Pickin’ on Nashville,” which charted four consecutive Top 40 country singles. This led to a notable career with the band releasing ten studio albums featuring twenty-three singles.
The band’s highest-charting single was a cover of “Oh Lonesome Me,” which reached number eight on the Billboard Hot Country charts. For their musical success, The Kentucky Headhunters have won three Country Music Association Awards, an Academy of Country Music Award, and a Grammy Award. (Learn about the most popular musical artists who’ve never had a No. 1 hit.)
Cage The Elephant
- Hometown: Bowling Green
Cage the Elephant is a rock band from Bowling Green, Kentucky. The band first rose to prominence with the release of its debut album, “Cage the Elephant.” This album produced several singles including “Ain’t No Rest for the Wicked,” which reached 32 on the UK Singles Chart.
Since then, the band has released a handful of albums, all featuring charting singles. Their synthesis of punk, blues, and rock has also earned Cage the Elephant numerous accolades. Besides a nomination for an MTV Video Music Award for Best Rock Video, the band has won two Grammy Awards.
The Everly Brothers
- Hometown: Brownie
Two of the biggest musicians from Kentucky are, no doubt, The Everly Brothers. Consisting of Phil and Don Everly, the duo first rose to prominence with the no. 1 hit song “Bye Bye Love.” From there, the duo released a string of hit albums and singles including “Wake Up Little Susie” and “Problems.”
Though The Everly Brothers’ musical output simmered after the brothers joined the Marines in the early 1960s, their brief run would influence musicians such as the Beach Boys and the Beatles, due to their combination of acoustic guitar playing and close-harmony singing. For their success, The Everly Brothers were inducted into the Rock and Roll Hall of Fame and the Country Music Hall of Fame.
Mary Travers
- Hometown: Louisville
Born Mary Allin Travers, Mary Travers was a singer-songwriter. She first rose to prominence as one part of the wildly successful musical trio Peter, Paul, and Mary. Though the group broke up shortly after releasing their no. 1 hit song “Leaving on a Jet Plane,” Travers would embark on a successful solo career.
During this time she released several albums including “Mary,” “Morning Glory,” and “Circles.” Peter, Paul, and Mary would reunite in the late 70s, however, and release a string of new albums as well as tour extensively. For their success, the trio was inducted into the Vocal Group Hall of Fame in 1999. Mary Travers died in 2009 from leukemia.
Bill Monroe
- Hometown: Rosine
One of the biggest musicians from Kentucky is, no doubt, Bill Monroe. Born a little after the turn of the 20th century, Monroe would become one of the most influential musicians of all time and earn the title “The Father of Bluegrass.” Over his long and storied career, Monroe released the now-class bluegrass songs “Molly and Tenbrooks,” “Wicked Path of Sin,” and “Blue Moon of Kentucky.”
For his success in practically creating a new genre of music, Monroe received countless accolades during his career. Besides being made an honorary Kentucky Colonel, Monroe was inducted into the Country Music Hall of Fame, the Rock and Roll Hall of Fame, and the Nashville Songwriters Hall of Fame. He also received a Grammy Lifetime Achievement Award and a National Medal of Arts. (Discover the 25 biggest hits of the 60s according to Billboard.)