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Top 10 Most Famous Male Country Singers Of All Time

Country music has gone through plenty of changes since the end of the Second World War. Before that, it had a totally different persona, even if some of the music was the same. It changed because it had to.

And those changes also influenced the country artists, the way they looked, and the styles of music that were now considered “Crossover Country.” But there was one thing that didn’t change.

In Their Blood

Some singers have a natural feel for the music they perform. Opera is one such genre. Country music is another. In some musical styles, you don’t need to feel an affinity with the music. But, with Country, it seems you need that relationship.

It is something you are usually brought up with. Almost like a family heirloom, passed down from parents to children. It isn’t something you can pretend to have, although some try.

With that said, I’m going to take a look at the most famous male country singers of all time. These choices are always going to be subjective, of course. It is all a matter of opinion, and we are all different, thankfully.

Country… Are You Sure?

There is at least one singer on the list who people might think, “Country singer?” He was a man known as “The Genius.” A man who crossed genres. A man who sang two of the greatest country hits of all time, he has to be here.

Who Is Missing?

Plenty, I suspect. One of those would be The Everley Brothers. They started their careers in Country and Folk tunes, but they were whisked away into Rock n Roll and Pop. But, even though they aren’t included, they didn’t ever forget their Country roots.

And The Rebels

Of course, we have a couple who kicked against those who controlled Country music in Nashville. Some of the greatest male Country singers didn’t like their conservatism and rebelled. I have at least one of those as well.

So, let’s take a look at some of these people who helped to shape Country music over the last eighty or so years. And I am not talking about those that put on a cowboy hat and boots and do the pretense thing. I am talking about real country music superstars. Those who have helped to shape the music and brought it to where it is today. Let’s start with a singer synonymous with Country music…

Top 10 Most Famous Male Country Singers Of All Time

Hank Williams

Hank Williams

When you think of Country music, Hank Williams is one of the first names that come to mind. Possibly one of the most influential Country singers. However, the boy born in Alabama wasn’t always the darling of Nashville.

Despite his standing and success, his life could not be described as a happy one. He couldn’t seem to shake off his addictions to alcohol or the overuse of drugs that had been prescribed to him. Because of these problems, his reliability as a performer was affected, and he was dismissed from the Grand Ole Opry.

In The Beginning

He had a band that played around Alabama, and neighboring Georgia called The Drifting Cowboys. They were one of the most popular acts around the area, and his name began to spread in the Southern states.

His first single, “Never Again (Will I Knock On Your Door),” was released in 1947. And in 1951, he released one of his most famous songs, “Hey Good Lookin’.”

However, his life and career were cut short…

Probably because of his inability to control his addictions, he died in 1953 on New Year’s day. He was just 29. Ironically, two of his greatest songs were released posthumously as singles in the year of his death. “Your Cheatin’ Heart,” a song that was included on the Memorial album, and “Take These Chains From My Heart.” Both reached #1 on the Country music charts.

Of course, both songs have been covered by plenty of artists. One of them will be included later on this list by another great Country singer. His life was brief and very troubled at times, but there is no denying he left a mark on Country music that remains to this day.

Kenny Rogers

Kenny Rogers

Now to a different and more modern breed of the Country singer. Rogers was born and raised in Texas to a family that you could say struggled financially. His music career started in the 50s and took him through Rock and Roll and even a brief flirtation with Psychedelic Rock.

He played bass and sang in the New Christy Minstrels in the mid-60s but then formed First Edition. As he took more control over their musical style, they moved more into Country music, where Rogers was most comfortable. The breakthrough came in 1969 with the Country-Pop song “Ruby Don’t Take Your Love to Town.”

The song was written by Mel Tillis. He later confirmed the soldier in question in the song was from World War Two, not Vietnam, as was popularly thought. It became an international success reaching #2 in the UK and #6 in America.

Rogers crossed genres at times…

As a result, he was a very different type of Country artist from the likes of Hank Williams. Although he would move into other genres, he would always come back to Country music. His collaborations with other artists were legendary, especially with Dolly Parton. Together they made many albums and DVDs.

Much admired by his County music associates and loved by his fans, he continued to work into the 2000s scoring a #1 hit in that year on the Country music chart with “Buy Me A Rose.” More than just a singer, though, his version of “The Gambler” became a TV series with Rogers in the lead role. He was made a member of the Country Music Hall of Fame in 2013.

Don Williams

Most Famous Male Country Singers Of All Time

It is no secret that American Country music isn’t top of most people’s choices in the UK. I was once given a three-month gig with a Country music band in the UK at the end of the 70s. I took it because I thought it would be a good experience. 

After finding out, one of my musical friends asked me if I was taking plenty of tissues with me to cry into. That is how it’s viewed by many, all doom and gloom, and I suppose there is some truth in it. 

A Sudden Surge

It was at a time, though, when there was a sudden surge in interest in the UK. There was line dancing, something I had never seen, cowboy hats, and the rest; it was all quite surreal. And the music they requested most? Don Williams.

Don Williams was a Country music singer you didn’t usually hear about. He wasn’t surrounded by controversy or addictions to start with, and he had a relaxed style. The British Country music fans loved and respected him. He released some great songs, such as “You’re My Best Friend” as well as “I Recall A Gypsy Woman.” But, as I remember, the big favorite was “Tulsa Time,” a line dancer’s favorite.

Musically, it wasn’t challenging, other than in one respect. You had to constantly resist the urge to over-embellish the bass lines. It was simple, and that was how it was supposed to be. Anything else and the “Country feel” had gone.

Even though Country music faded quite quickly in the UK…

Williams was always popular. I think he did his last tour there in about 2014 and was still able to get a big crowd. He never strayed too far musically from his country roots. He wrote dozens of songs recorded by others and also became one of Country Music’s biggest male singers in America.

Conway Twitty

Conway Twitty

Harold Lloyd Jenkins, or Conway Twitty as he became known, started his career singing Rockabilly in the 50s. But, it was as a Country singer that he became better known. Furthermore, he earned himself the nickname of “The High Priest of Country Music.”

As he started to become a known artist, he realized his name wasn’t going to help. He saw two places on a map, Conway in Arkansas and Twitty in Texas, hence the name.


His first few country releases were not played on Country music radio stations because he was known to be a bit of a rock and roller. Aren’t some people just pathetic? However, he broke through with a #5 hit in 1968, “The Image of Me.” He followed that up with “Next In Line,” which was his first #1 on the Country music chart.

From then on, he hardly had a single that didn’t make the Top 5. His songs went to #1 on the Country charts 40 times. That was a record held for 40 years until George Strait passed him. He also reached #1 on the main chart in America with the song “It’s Only Make Belief.” He wrote eleven of those top successes himself.

Outside of his solo work, his albums recorded with Loretta Lynn became famous and received many awards. After initially being banned from some stations, he became a Country music legend and ranks among the most famous male Country singers of all time. Good for him.

George Strait

George Strait

Let’s carry on with George Strait, the man who took Conway Twitty’s record. Strait was a breath of fresh air for the more conservative Country music people in Nashville and elsewhere.

The 1980s had been influenced by the new style of Country Crossover artists. Some of the “hardliners” scorned the likes of Shania Twain and Faith Hill for daring to step outside “The Format.”

George blew into town with a cowboy hat and boots and refreshed the image of Country music to those who thought it had lost its way. They rejected him at first but then had a change of heart. He became one of the most successful male Country singers ever with songs like “Amarillo By Morning” and “Unwound.” Known by some as “The King of Country,” he still performs today.

Charley Pride

Charley Pride

Charley Pride had been a professional baseball player before he turned to singing Country music. He was one of only three African-Americans elected to the Grand Ole Opry during his career.

Charley signed with RCA Records and became their best-selling artist since Elvis. He had thirty #1 hits on the Country music chart. One of those was “Kiss an Angel Good Mornin’,” which reached #21 on the American chart and #1 in the Country chart. He also had success with plenty of albums and compilations. A relaxed and smooth voice made him a Country favorite.

Merle Haggard

Merle Haggard

Another rebellious character in the Country music world. He also went to San Quentin but not to give free concerts like Johnny Cash. He was a “guest,” shall we say. On his release, he reformed and became a Country music legend. One of his great abilities was to talk about his life from a working-class background and put those experiences into his songs. 

He wrote songs that were supportive of the Vietnam war and the soldiers going to serve, which was a novelty at the time. One of his songs, “Okie From Muskogee,” mentions that. If you haven’t heard too much of Merle Haggard, Hag: The Best Of Merle Haggard is a good place to start.

Ray Charles

Ray Charles

I mentioned earlier someone you might not think of as a famous Country Music singer. This was a man known in the music business as “The Genius.” A man who ignored genres and their stipulations. He sang Blues, R&B, Gospel, Rock&Roll, and Country. Furthermore, he was responsible for two of the greatest country music recordings ever, in my opinion.

One of those songs I already have included – “Take These Chains From My Heart” by Hank Williams. But one of Ray Charles’s greatest recordings was “I Can’t Stop Loving You,” which was written by Don Gibson. In 1962, his version went to #1 in the UK and America. 

Billy Joel said that “Ray Charles was more important than Elvis Presley.” He probably was. He also made some outstanding Country albums such as Modern Sounds In Country And Western Music, Vol. 1 & 2. Ray Charles was inducted into the Country Music Hall of Fame in 2021

Willie Nelson

Willie Nelson

Another figure is instantly recognizable, not only by how he looks but by his voice. He was raised by his grandparents during the Great Depression and started playing and writing music very early.

Nelson got a job in Nashville writing for others, and one of his first major successes was the song “Crazy” recorded by Patsy Cline. He left Nashville after several run-ins with the “powers that be” and moved back to his home state of Texas. During the 70s, he made some great country albums, like Shotgun Willie in 1973. But, the album that kick-started his career was Red Headed Stranger from 1975.

Having been somewhat marginalized by the ultra-conservatives in Nashville, he got together with other like-minded musicians. This gave birth to a Country music sub-genre known as “Outlaw Country.” An appropriate name.

Like many of his peer group…

Willie had his run-ins with authority figures outside of music, the IRS being one. But I am not dwelling on that. That would be a disservice to a highly talented figure in the world of Country music.

Pick just one song he is famous for? How about “Always On My Mind“? These days he still plays when he can and is a serious activist for various causes. Rebels never grow old. Whenever country music is mentioned, the name of Willie Nelson will be spoken about. One of the most famous male Country singers of all time and a great man.

Johnny Cash

Johnny Cash

And so, to the last name, and realistically where else could we have finished? He was a country singer to the core, but he was also able to mix a bit of Blues, Rock&Roll, and Folk into his repertoire.

He was the son of poor cotton farmers from Arkansas, and he didn’t take too much from most people. His life was, at times, turbulent. Drug abuse, and trouble with the law, he had an outlaw-type image and lived up to his reputation much of the time.

His Signature Tune?

He didn’t have one, he had many. Songs like “Folsom Prison Blues” and another ‘prison’ favorite, the album recorded live at San Quentin, a place he despised. But he had a lighter side. 

He loved the old “railroad” style songs, like “Orange Blossom Special.” And there was also an often hidden lighthearted comedic side to his nature with songs like “A Boy Named Sue.” He was responsible for some classic songs of the Country music genre with, “I Walk the Line” and “Ring of Fire.”

June Carter

Marrying Country music artist June Carter may well have been what saved him. He mellowed, and his songs became softer. He still had the occasional relapse, but now he wasn’t permanently hell-bent on personal destruction.

His faith became important to him, and he took up the challenge of helping underprivileged people like the Native Americans. He was the youngest ever living singer elected to the Country Music Hall of Fame.

June had an enormous influence on him for the good, and his devotion to her was clear for all to see. He died just four months after her. If you want a legendary male Country music singer, Johnny Cash, “The Man in Black” was the real deal.

Looking for More Great Country Music?

If so, have a look at our detailed articles on the Most Famous Female Country Singers Of All Time, the Most Famous Black Country Singers, the Top Country Singers with Deep Voices, the Best Country Love Songs, and the Best 90s Country Songs for more rip-roaring song selections.

Of course, you need to hear them. So, check out our in-depth reviews of the Best Headphones for Music, the Most Comfortable Headphones, the Best Sound Quality Earbuds, the Best True Wireless Earbuds, and the Best Bluetooth Headphones Under $200 you can buy in 2023.

Most Famous Male Country Singers Of All Time – Final Thoughts

Since Country music became popular in its most basic form in the 1920s, it has undergone some big changes. It was once known as “Hillbilly” music. That was seen as offensive to some, and after the Second World War, efforts were made to change its image and refer to it as “Country and Western.”

Today, it includes other sub-genres like Rockabilly and Bluegrass. And, of course, the modern Country-Pop and Country-Rock styles of people like the early Eagles, Linda Ronstadt, and others.

A National Institution

That is how Country music could be described. Having said that, it is not a genre that is popular everywhere. But, where it is, it has become a national institution. And the participants have become heroes.

Outside of America, it is not a culture that is understood by most. It is often criticized as being morbid and depressing, which, to be fair, it can be. There aren’t too many “happy” country songs. The storylines can also be very much the same.

But that is the nature of Country music, and the artists we have looked at here have helped to mold it into what it has become. And, to those that follow it, Country music is more than a hobby. It is a way of life.

Until next time, happy listening.

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About Joseph L. Hollen

Joseph is a session musician, writer, and filmmaker from south Florida. He has recorded a number of albums and made numerous short films, as well as contributing music to shorts and commercials. 

He doesn't get as much time to practice and play as he used to, but still manages (just about!) to fulfill all his session requests. According to Joseph, it just gets harder as you get older; you rely on what you learned decades ago and can play without thinking. Thankfully that's what most producers still want from him.

He is a devout gear heat and has been collecting musical instruments all his life. As his wife, Jill, keeps on saying, "You're very good at buying nice instruments, but terrible at selling them!".

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