50 Greatest Country Artists of All-Time: Part Five (10–1)

Nathan Kanuch
Jul 4 · 9 min read

And so we’ve arrived! The 50 greatest country artists of all-time is down to the top ten. Here we go!

10.) Kris Kristofferson

Kris Kristofferson changed Nashville. Simple as that. Before the former Rhodes Scholar and US Army Captain arrived in town, Nashville was a place of formulaic songwriting- not bad, just predictable- but there was no one really writing songs in a poetic, literary way. Kristofferson showed up and gave country music such pieces of art like “Help Me Make It Through the Night,” “Sunday Mornin’ Comin’ Down,” and “Me and Bobby McGee.” These were songs that revolutionized Nashville and helped spark the fire for the outlaw movement. But it wasn’t just outlaw artists who were interested in his songs. Ray Price recorded “For the Good Times,” and Faron Young covered “Your Time’s Comin’.” Kris Kristofferon’s insistence on doing things *his* way provided a platform and blueprint for future artists to come. Kris and Townes are 1A and 1B when it comes to the greatest songwriters in music history.

Essential songs: “Help Me Make It Through the Night,” “Sunday Mornin’ Comin’ Down,” “Me and Bobby McGee,” “To Beat the Devil,” “Lovin’ Her was Easier,” “The Taker,” “For the Good Times,” “If You Don’t Like Hank Williams,” “Why Me,” and “Best of All Possible Worlds”
Essential albums: Kristofferson, The Silver Tongued Devil and I, and Jesus Was a Capricorn

9.) Alan Jackson

34 number one hits- 24 of which he had a major hand in writing. That is an unreal output. Alan Jackson’s understated, common-man career is truly historic. Steadfast in his defense and championing of traditional country music (long ago inspired by George Jones advising Jackson to “keep it country”) and a respectful admirer of country’s greatest artists, Alan Jackson is the definition of everything that’s right about country music. All Alan ever wanted to do was write and sing stone-cold, country gold. He’s succeeded and then some.

Essential songs: “Here In The Real World,” “Chasin’ That Neon Rainbow,” “Don’t Rock the Jukebox,” “Tonight I Climbed the Wall,” “Gone Country,” “(Who Says) You Can’t Have It All,” “Little Bitty,” “Where Were You (When the World Stopped Turning),” “Remember When,” “Everything I Love,” “Angels and Alcohol,” and “Small Town Southern Man”
Essential albums: Here In The Real World, Who I Am, Everything I Love, Under The Influence, The Bluegrass Album, and Angels and Alcohol

8.) Loretta Lynn

Some artists, like Alan Jackson above, build their careers as a body of work, and we look back impressed at the overall story. Others, like Loretta Lynn (in my opinion), become legends thanks to a large amount of *big* moments. Recording one of the ultimate autobiographical songs with “Coal Miner’s Daughter.” Winning ACM Artist of the Decade for the 1970s. Recording and releasing controversional material at the time like “Dear Uncle Sam,” “Rated X” and “The Pill.” Dueting on a series of hits with Conway Twitty. Experiencing a career revival with the Jack White-produced Van Lear Rose. Loretta Lynn is not just the greatest female country artist of all-time. She’s one of the greatest musical artists to ever record music.

Essential songs: “Coal Miner’s Daughter,” “Don’t Come Home A-Drinkin’ (With Lovin’ On Your Mind),” “You Ain’t Woman Enough (To Take My Man),” “Fist City,” “The Pill,” and “Portland, Oregon”
Essential albums: You Ain’t Woman Enough, Fist City, Coal Miner’s Daughter, You’re Lookin’ At Country, and Van Lear Rose

7.) Merle Haggard

The Poet of the Common Man. While artists like Kristofferson and Townes van Zandt made beautiful, intellectual music, Merle Haggard was writing and singing about the most usual of things in the simplest of terms. And yet it was the ease at which The Hag wrote and sung his songs that resonated. He was as authentic as an artist could get. He, like all of the other legends listed here, truly lived what he wrote. Perhaps the most amazing thing about Haggard was the simple subject matter of his songwriting. Reading the lyrics, a newcomer to country music may believe everyone writes in the manner of The Hag. And yet…no other artist has been able to reach that level. “Silver Wings,” for example, begins with the chorus followed by the bridge and then two more repetitions of the chorus before ending. Take that to a publisher, and you’d be laughed out of the room. And yet Merle Haggard made it a country standard.

Essential songs: “Mama’s Hungry Eyes,” “Mama Tried,” “Tonight The Bottle Let Me Down,” “I Think I’ll Just Stay Here and Drink,” “If We Make It Through December,” “Sing Me Back Home,” “Workin’ Man Blues,” “Daddy Frank,” “My Favorite Memory,” “Big City,” and “A Place to Fall Apart”
Essential albums: Sing Me Back Home, Mama Tried, Same Train, Different Time, Serving 190 Proof, The Way I Am, Back to the Barrooms (The trio of albums from Serving 190 Proof to The Way I Am to Back to the Barrooms is arguably the greatest run of albums in country music history).

6.) Willie Nelson

I remember seeing Willie Nelson with my Grandpa in 2014. He came out on stage, picked up Trigger, and strung the first few notes to “Whiskey River,” and time stood still. Willie is an American Original who marches to the beat of his own drum. Always has. A hit Nashville songwriter in the late 50s and early 60s, Willie grew tired and disillusioned with Music Row and moved back to Texas in the early 70s. Recording fantastic concept albums, Willie waged war with Waylon against the establishment and won. And he’s been cultivating his rich legacy ever since. Where would country music be without Willie?

Essential songs: “The Party’s Over,” “Yesterday’s Wine,” “Stay All Night (Stay A Little Longer),” “Red Headed Stranger,” “Time of the Preacher,” “Bloody Mary Morning,” “Blue Eyes Crying in the Rain,” “On the Road Again,” “Always On My Mind,” and “City of New Orleans”
Essential albums: …And Then I Wrote, Willie Nelson & Family, Yesterday’s Wine, Shotgun Willie, Phases and Stages, Red Headed Stranger, To Lefty From Willie, Me & Paul, Country Music, and Band of Brothers

5.) Johnny Cash

The Man in Black. A unfiying figure for country and rockers. An artist who transcends, well, everything. Johnny Cash’s contributions to country music and the American songbook are long, lengthy, and abundant. An American rebel who spoke out for the broken and downtrodden but could fit right in with his own television show reaching people of all ages and musical persuasions. Cash used his platform for good, above all else, reminding us even today that there *are* things that can bring us together.

Essential songs: “I Walk the Line,” “Ring of Fire,” “Big River,” “Get Rhythm,” “Cocaine Blues,” “Man in Black,” “Hey, Porter,” “Hurt,” “Down There By The Train,” “Folsom Prison Blues,” “San Quentin,” “Daddy Sang Bass,” “Sunday Mornin’ Comin’ Down,” and “God’s Gonna Cut You Down”
Essential albums: Johnny Cash with His Hot and Blue Guitar, Blood, Sweat, and Tears, Bitter Tears: Ballads of the American Indian, Sings the Ballads of the True West, American Recordings, American IV: The Man Comes Around, Johnny Cash at Folsom Prison, Johnny Cash at San Quentin

4.) Buck Owens

There would have never been a Bakersfield Sound at a popular level were it not for Buck Owens. Buck Owens, along with his guitar player Don Rich (Buck actually taught Don how to play), pioneered a twangy, drum and steel guitar driven sound that would influence countless artists to come. His songwriting is underrated, as is his guitar playing. And yet you hear his influence everyday, whether you’re listening to Merle Haggard, The Byrds, Brad Paisley, Dwight Yoakam, or Jon Pardi. In fact, sonically, I’d argue Buck is one of the most influential artists in music history. So many want and search for that Bakersfield Sound. And it was mastered by one man- Buck Owens.

Essential songs: “Together Again” (featuring, in my opinion, the greatest steel guitar solo in country music history), “Act Naturally,” “Buckaroo,” “Under Your Spell Again,” “I’ve Got a Tiger by the Tail,” “Foolin’ Around,” “Hello Trouble,” “Cryin’ Time,” and “My Heart Skips a Beat”
Essential albums: 21 #1 Hits: The Ultimate Collection, Carnegie Hall Concert, In Japan!, and Buck Owens Sings Tommy Collins

3.) Hank Williams

The Hillbilly Shakespeare. No songwriter in American music history has so nailed the human condition so simply. Hank is simply the gold standard of country music. He’s been imitated and admired by each and every artist who’s ever recorded country music. “I’m So Lonesome I Could Cry” contains the most poignant imagery one could ever find in a song. Hank’s tragic life only seemed to enhance his legend, and the words he penned live on to this day. And will continue to live on long after we’re all gone. Hank took simple songs and brought them to the whole country, thus making country music more than just a regional phenomenon.

Essential songs: “I’m So Lonesome I Could Cry,” “Jambalaya (On the Bayou),” “Moanin’ the Blues,” “Ramblin’ Man,” “Lost Highway,” “A Mansion on the Hill,” “Cold, Cold Heart,” “Honky Tonkin’,” “Honky Tonk Blues,” “I Saw the Light,” “I’ll Never Get Out of this World Alive,” “Move It On Over,” and “You Win Again”
Essential album: 40 Greatest Hits

2.) Waylon Jennings

The quintessential outlaw. Waylon fought the system from Music Row itself. And when the system got a little too friendly for him, he left. Waylon wanted to be an artist living on the edge. Influencing the mainstream but with enough freedom to be left alone. Waylon’s music had defining characteristics- Ralph Mooney’s steel guitar partnered with Waylon’s telecaster, Richie Albright’s driving backbeat. Waylon could also slow it down and be tender when necessary. Unlike so many of the copycats (then and now), Waylon was well aware of what the outlaw lifestyle was doing. He had a $1,500 a day cocaine habit that was going to kill him before he quit cold turkey in the early 80s, never to go back to the powder. Waylon Jennings owns three rich periods in his career to his name, all of which contributed to his legacy. The pre and post outlaw years combined with the 1970s made Waylon an indomitable and inevitable force.

Essential songs: “Amanda,” “Lonesome, On’ry and Mean,” “I’m a Ramblin’ Man,” “The Last Letter (Live),” “Are You Sure Hank Done It this Way,” “The Taker,” “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” “I’ve Always Been Crazy,” “Dreaming My Dreams With You,” “Leavin’ Town,” “Time to Bum Again,” and “Will the Wolf Survive”
Essential albums: Waylon Live, Lonesome, On’ry and Mean, Ladies Love Outlaws, Dreaming My Dreams, Honky Tonk Heroes, Leavin’ Town, and Will The Wolf Survive

1.) George Jones

And at number one…who else? George Jones’ voice sounded like an instrument itself, as if George was reaching down deep inside and feeling every single note in his heart. A George Jones song makes the listener feel something that he or she has never felt before. The way he could drag out a note for seemingly forever before casually letting it go was just legendary. A man who lived a tragic, addiction-riddled life and yet somehow lived to the age of 82. He was haunted by demons and turned that torture into the best music we could ask for. I cried the day George Jones died and still tear up time to time when a song of his comes on. The best of the best. A true American Icon. And the greatest country artist of all-time.

Essential songs: “He Stopped Loving Her Today,” “The Grand Tour,” “Who’s Gonna Fill Their Shoes,” “The Race Is On,” “If Drinkin’ Don’t Kill Me,” “The Door,” “Choices,” “Hell Stays Open All Night Long,” “Still Doin’ Time,” and “I’ve Aged Twenty Years In Five”
Essential albums: George Jones, The Grand Tour, I Am What I Am, Still the Same Ole Me, and Cold Hard Truth

Shore2Shore Country

A different kind of look at country music. Opinions and historical examinations of America’s greatest genre along with updates on the current state of country music.

Nathan Kanuch

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Graduate of W&J College 2016.

Shore2Shore Country

A different kind of look at country music. Opinions and historical examinations of America’s greatest genre along with updates on the current state of country music.