15 Best Male Country Singers That Are Absolute Legends

Country music has been an important part of the musical and cultural fabric of America for nearly one hundred years. Often telling tales of sorrow and desperation, country singers have been some of the primary poets and songwriters of the modern era. Join me as we look at some of the best male country singers through all eras of country music history. 

15 Best Male Country Singers (TLDR)

The rich history of country music has provided us with a whole host of different talents over the years. One of the best modern male country singers is Tyler Childers, a young talent with an old school country feel.

Of course, no discussion of country music would be complete without mentioning George Jones, whose classics such as “White Lightning” have become definitive country anthems.

Another great talent in the country world was Roy Acuff, a highly influential Nashville singer who started his country career back in 1932.

1. George Jones

Often referred to as “the Possum,” don’t let the unassuming nickname fool you—George Jones was one of the most formidable singers in country music for decades. He has a soulful and emotional voice.

One of Jones’ strengths was that he was never afraid to show his vulnerability, and his singing and songwriting have influenced just about all country artists since he first hit the scene in the 1950’s. 

Favorite Song by George Jones: “The Grand Tour” is Jones at his most heartfelt. Released in 1974 when Jones had already been in the business for a couple of decades, the song is an autobiographical tale detailing the slow dissolution of a marriage. There is so much desperation and emotion in Jones‘ voice here.

2. Roy Acuff

Roy Acuff is one of the true country music originals, and many of the country masters of the 50’s and 60’s borrowed heavily from Acuff’s style. Often utilizing a gruff and raspy voice, he explored many styles from bluegrass to folk and laid down the foundations of what country would become. 

Favorite Song by Roy Acuff: “Wabash Cannonball” is one of Acuff’s most well-known classics for a reason, and it has endured since the 1940’s. A reworking of a popular folk song that dates to the 19th century, this is a rollicking, upbeat tale of a train that has been the witness to many events through history. 

3. Hank Williams

Perhaps the originator of outlaw country, Hank Williams is an essential in the country music pantheon. Although he never even made it to thirty years old, Williams wrote many great songs in his lifetime, like “I’m So Lonesome, I Could Cry” and “Your Cheatin’ Heart.” He often sang ballads about love and loneliness and had so much conviction in his voice.

Favorite Song by Hank Williams: “Six More Miles (To the Graveyard” is an especially dark and harrowing track in the Williams catalogue, describing a tale of a man who must travel to bury his wife who has just passed away. This is one of the most emotional songs in the Hank Williams repertoire.

4. Bill Monroe

Influencing everyone from Elvis Presley to Waylon Jennings to Jerry Garcia, Bill Monroe is often referred to as the “father of bluegrass.” Credited with popularizing the genre of bluegrass and helping lay the foundation for modern country music, songs like “Blue Moon of Kentucky” display Monroe’s great mandolin skills and his passionate voice.

Favorite Song by Bill Monroe: “Uncle Pen” is a fun, upbeat, and folky track. Monroe‘s voice is often indecipherable, but he sings with a lot of passion and fits the music so well.

5. Tyler Childers

Coming back to the modern era, Tyler Childers is a country artist from the 2010’s who’s been making waves for a while. Born in 1991, Childers brings back the harrowing ballads and tales of desperation of old school country music. Childers has a raw, stripped down, “everyman” style of vocals, but it fits the dark and haunting tales he tells in his music. 

Favorite Song by Tyler Childers: “Feathered Indians” is the standout track on his 2018 album, Purgatory. Childers weaves an enchanting story of the relationship between a religious woman and a wild guy, and his voice is delicate while still powerful. 

6. Johnny Cash

Back to one of the old school giants of country, Johnny Cash’s raspy baritone voice is something that’s tragically been in short supply since the artist’s death in 2003. Johnny Cash had so much grit and passion in his voice, it’s no wonder he was able to transition to rock music so easily later in his career. Cash’s music spanned many genres, but his beloved country classics put him on the map.

Favorite Song by Johnny Cash: “The Big Battle” is an overlooked deep cut that might not be as talked about as “Walk the Line” or “Ring of Fire,” but I think it perfectly demonstrates Cash’s talent as a singer and a storyteller. The way he assumes the role of the Civil War characters he sings about in this track almost transports the listener back in time.   

7. Buck Owens

Owens is another one of the originals, and he had 21 number one hits to prove it. Owens hailed from Texas and spent a lot of time writing in California, so he brought a more explicitly western sound to the country pantheon. His music and voice evoke the images of outlaw cowboys and desert highways.

Favorite Song by Buck Owens: “Act Naturally” is a classic Buck Owens song, a tale that’s both sorrowful and humorous at the same time. Owens assumes the character of a man who has been hired to play a lonely man in a film, and the singer reflects that he won’t even have to do any acting for the role. 

8. Marty Robbins

If you’re looking for a classic country artist who perfectly encapsulates the feeling of an old Western movie (or a game like like Red Dead Redemption), check out Marty Robbins. His entire Gunfighter Ballads and Trail Songs album from 1959 sounds like a snapshot of the 1800’s, and Robbins’ convincing voice and expert storytelling skills paint such vivid images. 

Favorite Song by Marty Robbins: “Big Iron,” famous for its use in Fallout: New Vegas, is a tale of gunslingers and duelists of the old wild west. Robbins has the perfect voice for his tale of outlaw gunmen, making me want to dig out my Clint Eastwood and John Wayne DVDs. 

9. Steve Earle

One criminally underrated and especially talented singer/songwriter is Steve Earle, a country artist who has dabbled in bluegrass, rock, folk, and even blues at times. Earle is known for his politically charged lyrics and fixation on the American working class, which gives his vocals and music a down-to-Earth and soulful feel. 

Favorite Song by Steve Earle: “Copperhead Road” is an old classic by Earle telling the tale of a down and out war veteran. Earle’s voice has a lot of swagger and rock ‘n roll energy to it, which makes him stand out in the country world. 

10. Hank III

He looks and sounds like his grandfather Hank Williams, but Hank III has a totally unique spin on country he can call his own. Drawing influence from the old school country greats and genres as diverse as heavy metal and punk rock, Hank III brought some much-needed energy to the country scene when he released his best album, 2006’s Straight to Hell.  

Favorite Song by Hank III: “Country Heroes” shows Williams giving tribute to the country legends of old, from his grandfather to George Jones. While Hank III is mostly known for his high energy party anthems, “Country Heroes” is a sorrowful ballad that looks back on all the country musicians we’ve lost over the years.

11. Merle Haggard

Merle Haggard was famous for his outlaw redneck style, but as a singer he had a lot of heartfelt and passionate moments, and as a songwriter he could tackle some seriously emotional topics. He could sound wistful and longing, or he could sound like a cowboy party animal on a moment’s notice.

Favorite Song by Merle Haggard: “The Bottle Let Me Down” is Haggard’s finest ballad. Haggard sounds truly pained as he tells a tale of a man struggling with alcoholism and relationship struggles. His voice makes you feel like you know the main character.

12. Townes Van Zandt

Van Zandt was an enigmatic figure who lived in relative obscurity through most of his career. Thankfully, his soulful crooning and storytelling skills have enjoyed a resurgence in the decades following his untimely death in 1997. His voice had such a great sense of melancholy, and he tackled topics ranging from drug addiction to mental illness, different from the mainstream country of his time.

Favorite Song by Townes Van Zandt: “Pancho and Lefty” is Van Zandt’s best-known track for a reason. This ballad travels back to the time of bandits and outlaws, and Van Zandt’s voice evokes this atmosphere perfectly. 

13. George Strait

In the late 80’s George Strait was one of the hottest singers in country music, and he had the talent to back up his success. Strait is noteworthy for having a traditional 40’s and 50’s country voice but putting his own modern twist on the style. His voice fits the swinging style of his music. 

Favorite Song by George Strait: “All My Ex’s Live in Texas” was one of Strait’s biggest hits and most iconic anthems. It’s a lighthearted and humorous number with a larger-than-life, party country sound. It makes me want to dance around with a lasso at the honky-tonk.

14. Willie Nelson

Willie Nelson is pushing 90 years old and still going strong. Often dubbed the “redheaded stranger,” Nelson was one of the biggest and best country singers of the 70’s and 80’s. Nelson has a unique talent of wielding an often tranquil and soothing voice, but his incredible range allows him to get loud and over-the-top at times as well. 

Favorite Song by Willie Nelson: “Whiskey River” is a Willie classic from 1973, an upbeat ode to drinking away one‘s sorrows after a bad relationship. This is one of Willie’s more rocking tunes.

15. Waylon Jennings

Jennings was one of the innovators who put outlaw country on the map in the 60’s and 70’s, with his raw and unrefined vocals fitting his music and lyrics perfectly. Nobody quite sounded like Jennings, and that remains the case to this day. Jennings’ voice had a rock ‘n roll edge to it, which sets him apart from other country artists of the era.

Favorite Song by Waylon Jennings: “I’ve Always Been Crazy” is a fun party anthem where Waylon looks back on all the hijinks he’s engaged in. Whether the song is autobiographical or not, Jennings sings in a way that makes you believe every word of it. 

There you have it, folks: 15 of the best male country singers the music industry has ever known. I covered some classic country singers from all eras of the genre’s history, and I hope anyone reading can see that country music has a rich and varied history of legendary singers to offer.   

This article was written by Avery and edited by Michael.

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