Music

The Best Country Singers From Kentucky  

Ranker Music
992 votes 203 voters 4.3k views 52 items

List Rules Only country singers born or raised in Kentucky.

Here are the best country artists and country bands from Kentucky. Kentucky has served as the birthplace of many fantastic country artists. The sound of twanging guitars has permeated the state for decades. In particular, Renfro Valley, which is home to the Kentucky Music Hall of Fame as well as the Renfro Valley Entertainment Center, has been dubbed Kentucky's Country Music Capital. It is a destination where many influential artists got their start. Some of your favorite acts may be country singers from Kentucky, and this list gives you a chance to learn more about the singers and bands who changed your life. 

Chris Stapleton was born in Lexington. He's a singer in his own right, but he has also written over 170 songs for various other artists. He's a legend in his own right, and he represents everything Kentucky residents are capable of. Sturgill Simpson is another popular artist from the state. He brought back the stylings of outlaw country in a big way in recent years, and he's won various accolades, including a Grammy. 

Some of the the most famous country artists in the music industry are on this list. You can vote for your favorite Kentucky country singers and bands to let other readers know who they should be listening to. 

list ordered by
1
Chris Stapleton is listed (or ranked) 1 on the list The Best Country Singers From Kentucky
Chris Stapleton is an American country, bluegrass, and rock musician signed to Universal Music Group Nashville. He is an established songwriter. with four number one songs including the 5-week ...more
2
Tyler Childers is listed (or ranked) 2 on the list The Best Country Singers From Kentucky
Tyler Childers (born June 21, 1991) is an American country music singer and songwriter. He released his breakout album titled Purgatory in August 2017. The album was produced by Sturgill Simpson ...more
3
Loretta Lynn is listed (or ranked) 3 on the list The Best Country Singers From Kentucky
Loretta Lynn, is a multiple gold album American country music singer-songwriter whose work spans more than 50 years. She has received numerous awards and other accolades for her groundbreaking ...more
4
Tom T. Hall is listed (or ranked) 4 on the list The Best Country Singers From Kentucky
Thomas "Tom T." Hall is a retired American country music songwriter, singer, novelist, and short-story writer. He has written 11 No. 1 hit songs, with 26 more that reached the Top 10, ...more
5
Patty Loveless is listed (or ranked) 5 on the list The Best Country Singers From Kentucky
Patty Loveless, is an American country music singer. Since her emergence on the country music scene in late 1986 with her first album, Loveless has been one of the most popular female singers of ...more
6
Dwight Yoakam is listed (or ranked) 6 on the list The Best Country Singers From Kentucky
wm.e.mcintosh added
Dwight David Yoakam is an American singer-songwriter, actor and film director, most famous for his pioneering country music. Popular since the early 1980s, he has recorded more than 21 albums ...more
7
Sturgill Simpson is listed (or ranked) 7 on the list The Best Country Singers From Kentucky
John Sturgill Simpson (born June 8, 1978) is an American country music singer-songwriter. As of August 2017, he has released three albums as a solo artist. He released two albums independently, ...more
8
Montgomery Gentry is listed (or ranked) 8 on the list The Best Country Singers From Kentucky
Montgomery Gentry is an American country music duo composed of vocalists Eddie Montgomery and Troy Gentry, both natives of Kentucky. The two began performing in the 1990s as part of two ...more
9
The Judds is listed (or ranked) 9 on the list The Best Country Singers From Kentucky
The Judds were an American country music duo composed of Naomi Judd and her daughter, Wynonna Judd. Signed to RCA Records in 1983, the duo released six studio albums between then and 1991. One ...more
10
Chris Knight is listed (or ranked) 10 on the list The Best Country Singers From Kentucky
Chris Knight is an American singer-songwriter from Slaughters, Kentucky. In addition to releasing solo records of his own material, Knight has had a successful career writing songs that have ...more
11
Wynonna Judd is listed (or ranked) 11 on the list The Best Country Singers From Kentucky
Wynonna Ellen Judd is an American country music singer. Her solo albums and singles are all credited to the singular name Wynonna. Wynonna first rose to fame in the 1980s alongside her mother, ...more
12
The Everly Brothers is listed (or ranked) 12 on the list The Best Country Singers From Kentucky
The Everly Brothers were American country-influenced rock and roll singers, known for steel-string guitar and close harmony singing. Isaac Donald "Don" Everly and Phillip ...more
13
The Kentucky Headhunters is listed (or ranked) 13 on the list The Best Country Singers From Kentucky
The Kentucky Headhunters is an American country rock and Southern rock band. They were founded in 1968 as Itchy Brother, which consisted of brothers Richard Young and Fred Young along with Greg ...more
14
David
David Akeman, better known as Stringbean, was an American country music banjo player and comedy musician best known for his role on the hit television show, Hee Haw, and as a member of the Grand ...more
15
The Osborne Brothers is listed (or ranked) 15 on the list The Best Country Singers From Kentucky
The Osborne Brothers, Sonny Osborne and Bobby Osborne, were an influential and popular bluegrass act during the 1960s and 1970s. They are probably best known for their No. 33 1967 country hit ...more
16
Crystal Gayle is listed (or ranked) 16 on the list The Best Country Singers From Kentucky
Crystal Gayle is an award-winning American country music singer. Best known for her 1977 country-pop crossover hit song, "Don't It Make My Brown Eyes Blue", she accumulated 20 number ...more
17
Grandpa Jones is listed (or ranked) 17 on the list The Best Country Singers From Kentucky
Louis Marshall Jones, known professionally as Grandpa Jones, was an American banjo player and "old time" country and gospel music singer. He is a member of the Country Music Hall of
18
Troy Gentry is listed (or ranked) 18 on the list The Best Country Singers From Kentucky
Troy Gentry is a member of the musical group, Montgomery Gentry.
19
Naomi Judd is listed (or ranked) 19 on the list The Best Country Singers From Kentucky
Naomi Judd is an American country music singer, songwriter, and activist.
20
Billy Ray Cyrus is listed (or ranked) 20 on the list The Best Country Singers From Kentucky
William "Billy" Ray Cyrus is an American singer, songwriter, and actor. Having released twelve studio albums and forty-four singles since 1992, he is best known for his number one ...more
21
John Michael Montgomery is listed (or ranked) 21 on the list The Best Country Singers From Kentucky
jsmusicprincess85 added
John Michael Montgomery is an American country music artist. Montgomery began singing with his brother Eddie, who is one-half of the country duo Montgomery Gentry, before beginning his ...more
22
Will Oldham is listed (or ranked) 22 on the list The Best Country Singers From Kentucky
Will Oldham, better known by the stage name Bonnie 'Prince' Billy, is an American singer-songwriter and actor. From 1993 to 1997, he performed and recorded under variations of the Palace name, ...more
23
Skeeter Davis is listed (or ranked) 23 on the list The Best Country Singers From Kentucky
Mary Frances Penick, better known as Skeeter Davis, was an American country music singer who sang crossover pop music songs including 1962's "The End of the World". She started out as ...more
24
Th' Legendary Shack*Shakers is listed (or ranked) 24 on the list The Best Country Singers From Kentucky
The Legendary Shack Shakers are an American rockabilly/blues band that formed in Paducah, Kentucky in the mid-1990s. They are inspired by rock 'n roll, country blues, old time music, carnival ...more
25
Cliff Carlisle is listed (or ranked) 25 on the list The Best Country Singers From Kentucky
Cliff Carlisle was an American country and blues singer. Carlisle was a yodeler and was a pioneer in the use of the Hawaiian steel guitar in country music. He was a brother of country music star ...more