The 20 Greatest Male Country Singers Of All Time

There’s no doubt that country music is one of America’s most beloved genres. For decades, country artists have been thrilling fans with their down-home lyrics and twangy melodies. From Johnny Cash to Conway Twitty, there are some amazing country performers.

In this article, I’ll be counting down the 20 greatest male country singers of all time. These are the men who have defined what it means to be a country star, and who have left a lasting impact on the genre. Their music has resonated with fans across the world, and their influence is still felt today.

1. Johnny Cash

Starting off this list is the man in black himself, Johnny Cash. Cash is considered to be one of the most influential musicians of the 20th century. He is a country singer, songwriter, and guitarist who has sold more than 90 million records all over the world.

Some of his most famous songs include “I Walk the Line” and “Man in Black”. Cash is also known for his covers and his most popular cover was of the song “Hurt” by Nine Inch Nails.

He received several awards throughout his career including ones from the Country Music Association Awards and a few Grammys. There’s no doubt that Johnny Cash is one of the greatest male country singers of all time!

2. Bob Dylan

Bob Dylan has been influential in the world of music for over five decades. Dylan is known for his unique songwriting style which often includes social and political commentary.

He has released 39 studio albums and has sold more than 100 million records worldwide. A pretty impressive resume, no doubt!

Some of Dylan’s most famous songs include “Blowin’ in the Wind”, “Like a Rolling Stone”, and “The Times They Are a-Changin'”. He left a huge legacy not just as a musician, but as an icon of the counterculture movement.

3. Tim McGraw

The next country superstar on this list is Tim McGraw. McGraw has been making music since the early 1990s and has released 16 studio albums. He is married to fellow country star Faith Hill and the two have collaborated on several songs together.

He was able to cross over into the mainstream with songs like “Live Like You Were Dying” and “If You’re Reading This.”

McGraw has sold over 80 million records and is one of the best-selling artists of all time. He is also a three-time Grammy Award winner!

4. George Strait

This list won’t be complete without the King of Country himself, George Strait. He’s a legend in the industry and has been entertaining audiences for decades. Strait has had over 60 number-one singles on the Billboard charts, making him one of the most successful recording artists of all time!

His signature sound is traditional country music with a twist, and he’s inspired countless other artists throughout his career.

“Amarillo by Morning” is considered one of his most iconic songs, and it perfectly showcases his talent for storytelling through song. If you’re a fan of country music, then you’ve undoubtedly heard of George Strait!

5. Willie Nelson

Joining his first band at the age of 10 and going professional by touring locally in high school, Willie Nelson has been making music for over six decades.

Throughout his career, he’s been a part of 200 albums (solo, collaborations, etc.) and written some of the most iconic country songs of all time, including “On the Road Again,” and “To All the Girls I’ve Loved Before”.

He is one of the standard-bearers of the genre, and his impact on country music is impossible to overstate. He’s won multiple Grammy Awards, been inducted into the Country Music Hall of Fame, and was given the Kennedy Center Honors. He truly is one of the greatest male country singers of all time.

6. George Jones

Born in the small town of Saratoga, Texas, in 1931, George Jones started his musical career singing on the local radio station. He went on to release his first single in 1954, and he was soon a mainstay on the country charts.

Over the course of his more than 60-year career, he released 150 singles, including multiple Number 1 hits like “He Stopped Loving Her Today” and “The Grand Tour”.

George Jones was one of the most influential country singers of all time, and his impact can still be felt today. He is also known as “The Rolls Royce of Country Music” and it’s not hard to see why. He was a true legend, and will always be remembered in the history of country music.

7. Garth Brooks

Garth Brooks was a relative latecomer to the country music scene, releasing his first album in 1989 when he was almost in his 30s. But what he lacked in timing, he more than made up for in talent. His first album was a success and it ranked second on the Billboard Top Country Albums!

His career only got bigger from there. He would go on to release a total of 15 studio albums, most of which were certified diamond or multi-platinum. He’s won multiple Grammy Awards and Country Music Association Awards, and he was inducted into the Country Music Hall of Fame in 2012.

8. Merle Haggard

Next on the list is a Kennedy Center Honor awardee and a country music legend, Merle Haggard. Hailing from Oildale, California, Merle Haggard was one of the pioneers of the “Bakersfield sound” in country music.

He started his musical career playing guitar in honky-tonks and eventually released his first album in 1964.

Haggard went on to release 66 studio albums and had 38 Number 1 hits on the country charts. He remains one of the most respected and revered country singers of all time, and his influence can still be heard in country music today.

9. Hank Williams

The next icon on this list is Hank Williams. He was an American singer-songwriter and musician who has been credited with helping to shape the country music genre.

Williams had a string of hit songs throughout his career, including “Your Cheatin’ Heart” and “I’m So Lonesome I Could Cry.”

His contributions to country music are still celebrated today. He made use of simple, yet effective, storytelling in his songs which helped to connect with listeners. Williams passed away at the age of 29, but he left behind a legacy that has inspired many other country artists.

10. Waylon Jennings

You’re not a country music fan if you don’t know Waylon Jennings. He was one of the most prolific country singers of the 20th century and his music has been beloved by fans for decades. Jennings began his career in the 1950s as a bass player in Buddy Holly’s band, but he soon found success as a solo artist.

In a span of 26 years from 1965 to 1991, 96 of his singles reached the Billboard Country Charts, more than any other artist in that period. He is, without a doubt, a country legend. His works are still adored by country fans all over the world and his impact on the genre is undeniable.

11. Kenny Rogers

Kenny Rogers is a country music icon and one of the best-selling artists of all time. He’s enjoyed success in multiple genres, but he’s best known for his work in country music.

Some of his best-selling singles include “The Gambler,” and “Islands in the Stream.”

Rogers has been inducted into the Country Music Hall of Fame and he has won multiple Grammy Awards. He’s still touring and performing today and his music is as popular as ever! His most-viewed single on Youtube is his music video for “The Gambler” which now has over 177 million views!

12. Luke Bryan

The next male country singer on this list is Luke Bryan. Bryan is a well-known figure in the contemporary country music world, having released 7 studio albums and thirty-one singles. He is known for his catchy songs and energetic live performances.

What makes him one of the greatest male country singers of all time is his ability to connect with his fans. He is one of the few artists who can appeal to both country and pop audiences.

Despite joining the country music scene relatively late when compared to other names on this list, he has made a name for himself. His music is fun and upbeat, but it also has a relatable message that many people can relate to!

13. Blake Shelton

There wouldn’t be a list of the greatest male country singers of all time without Blake Shelton! Shelton is one of the most successful artists in the genre, having released 12 studio albums and over 50 singles. He is also a well-known television personality, thanks to his role as a judge on The Voice.

A lot of Shelton’s appeal comes from his down-to-earth personality. He is one of the most approachable and relatable stars in country music. His tracks are also full of catchy hooks and sing-along moments.

14. Alan Jackson

Alan Jackson is an American singer and songwriter. He is known for his traditional country music and his modern, mainstream country-pop sound. His songs are often about love, heartbreak, and loneliness.

If you’re looking for a country singer who can make you laugh, cry, and dance, then Alan Jackson is your man!

Some of his most remarkable tracks are “Remember When”, “Drive (For Daddy Gene)”, and of course “Where Were You (When the World Stopped Turning)”. Jackson is a member of the Grand Ole Opry and he has won numerous awards, including several Grammys.

15. Brad Paisley

Brad Paisley is one of the most successful singer-songwriters in the genre, with numerous awards and hits to his name. His music is often witty and humorous, and he is a master of both the guitar and vocals.

Paisley has a great sense of showmanship, and this is evident in his live performances. He always puts on a great show, whether he is performing solo or with a full band.

He is also known for his collaborations with other artists, including Carrie Underwood and Tim McGraw. Icons only work together if they are at the top of their game, and there is no doubt that Brad Paisley is one of the greatest male country singers of all time.

16. Chris Stapleton

Known as one of the most successful songwriters in Nashville, Chris Stapleton has penned hits for some of the biggest names in country music. He has also released 4 studio albums, all of which have been highly acclaimed by critics.

Most of his albums were big commercial successes, but his 2016 album “From A Room: Volume 1” topped the charts and won several awards including Album of the Year.

Stapleton’s music is often described as being “old-school” country, with a focus on storytelling and traditional instrumentation. He has a great voice, which can convey a lot of emotion in his songs. He is also a very talented guitar player and often uses his skills to great effect in his live performances.

17. Kenny Chesney

Kenny is a superstar in country music and has had many great songs throughout his career. He is known for his party anthems but also has some great ballads.

Some of his most popular songs include “Never Wanted Nothing More,” “When the Sun Goes Down,” and “How Forever Feels.”

He had over 40 tracks that reached the top 10 on the Billboard country charts. Also, he was able to receive a whopping eleven Academy of Country Music Awards! This only goes to show how popular and successful he is in the country music industry.

18. Conway Twitty

Conway Twitty was known for his unique voice and his ability to cross over into different genres. He had a total of 55 number-one singles on the country charts, which was a record that stood for more than 20 years.

His most well-known songs include “It’s Only Make Believe” and “Linda on My Mind.”

This list would not be complete without Conway Twitty. Just like other singers on this list, he was inducted into the Country Music Hall of Fame. He was a true pioneer in country music and will always be remembered in this industry.

19. Keith Urban

You might have seen Keith Urban on American Idol, mentoring the next generation of country singers. But before he was a judge on a reality television show, he was one of the artists reshaping country music in the 21st century.

Keith Urban is a master of neo-traditional country, a style that takes the best of traditional country and updates it for a modern audience. He’s also an incredible guitarist and has won four Grammy Awards. He is a real icon of country music, and one of the genre’s most successful singers.

20. Eric Church

Wrapping up this list of the greatest male country singers of all time is Eric Church. Eric Church is a country music rebel and has made a name for himself by bucking traditional country conventions.

He’s a fantastic singer and songwriter, and his songs are often about real-life topics that other country singers wouldn’t go near. He’s won multiple awards, including the Academy of Country Music’s coveted Entertainer of the Year award. What a legend!

Final Thoughts

That’s my list of the 20 greatest male country singers of all time! They all have unique voices and styles that have helped shape country music into the genre it is today. From Johnny Cash to Conway Twitty, there is sure to be an old-school or new-school artist that you like.

Bob Dylan Featured Image (Top-Right) by: Alberto Cabello from Vitoria Gasteiz, CC BY 2.0, via Wikimedia Commons
Willie Nelson Featured Image (Bottom-Left) by: Larry Philpot from Indianapolis, CC BY 2.0, via Wikimedia Commons