100 Greatest Country Artists of All Time: Singers Ranked - Rolling Stone
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100 Greatest Country Artists of All Time

From architects of the genre like Hank Williams and Jimmie Rodgers to game-changers Garth Brooks and Shania Twain

When putting together this ranking of country music’s all-time greats, we looked to movie criticism for inspiration. For decades Citizen Kane topped nearly every list as the greatest film ever made, but with time, some started to realize that, hey, just maybe The Godfather is the better picture. Likewise, we reevaluated exactly where Hank Williams fits into country music, the true influence of Merle Haggard, and if an artist as clearly in the pop realm as Taylor Swift deserves inclusion. (Spoiler alert: She does.)

Of course, while 100 artists is a lengthy list, there isn’t room for everyone. We didn’t include those who were primarily songwriters, like Hank Cochran and Harlan Howard. We respectfully skipped past Chet Atkins, who, though an architect of the Nashville Sound and a solo artist, was chiefly a sideman and producer. And we omitted both Elvis Presley and Ray Charles, whose admittedly important contributions to country music took a backseat to their work in rock & roll and soul.

For those who made the cut, we considered their lasting impact on the genre, their recorded output and even their legacy as an entertainer. Some of the contemporary artists we included – all of them already trailblazers – also benefited from our speculation that their best work may in fact be ahead of them.

But in the end, the common denominator for both legends and today’s stars was that they are all one-of-a-kind.

“Here’s the thing about history,” Vince Gill told Rolling Stone in 2014, “the greatest artists that had the greatest longevity were all original.”

UNSPECIFIED - CIRCA 1970: Photo of Webb Pierce Photo by Michael Ochs Archives/Getty Images

Webb Pierce

Though his flamboyant style and material excesses sometimes threaten to overshadow his actual work, Webb Pierce is still one of the honky-tonk era’s most expressive and successful performers, having accumulated more hits than Hank Williams or any of his contemporaries while he was hot. Born in West Monroe, Louisiana, Pierce applied his penchant for self-promotion and showmanship while on the Louisiana Hayride and found his way to a contract with Decca Records in Nashville. After joining the Grand Ole Opry, he was on top: he logged an extended series of radio hits that ranged from good-timing party music (“In the Jailhouse Now,” a 21-week Number One) and weepy drinking tunes (“There Stands the Glass”), delivered in a singular, emotive tenor. And sure, his offstage exploits were well-known. He had a lavish guitar-shaped pool constructed at his Nashville-area home, he wore dazzling Nudie suits and he covered two convertibles in silver dollars because why not? Though his traditionalist style faded from popularity, Pierce stuck stubbornly to his guns and stayed active through the Eighties. He died in 1991, but for a time in the Fifties and Sixties, he brought a little extra sparkle to the country charts. J.F.

Key Tracks: “In the Jailhouse Now,” “More and More,” “There Stands the Glass”

UNSPECIFIED - CIRCA 1970: Photo of Doug Sahm Photo by Michael Ochs Archives/Getty Images

Doug Sahm

Most country artists pray for a chance at the Grand Ole Opry stage, but Doug Sahm had to turn down an appearance in favor of his schoolwork when he was just a teenager. Born in San Antonio, Texas, Sahm was a prodigy – he could play almost any instrument, and could have easily gone the route of becoming the new Hank Williams: musical lore puts him on stage with Williams at his last show in Austin before he passed away, creating some sort of spiritual passing of the baton. Instead, Sahm used the Tejano sounds of his home state to sometimes go psychedelic, sometimes roots and sometimes pure rock & roll with his outfit, the Sir Douglas Quintet, which changed the landscape of Lone Star music forever and chiseled his own breed of Tex-Mex blues. “We wanted to be like the Rolling Stones and carry tons of shit in our suitcases and be heavy, you know,” he told Rolling Stone in 1971, “and turn everybody on.” M.M.

Key Tracks: “She’s About a Mover,” “Mendocino” 

CIRCA 1955: Country singer Hank Thompson poses for a portrait with his guitar in circa 1955. (Photo by Michael Ochs Archives/Getty Images)

Hank Thompson

A disciple of singing cowboy Gene Autry, Hank Thompson was one of country music’s first hard-edged honky-tonk performers and songwriters, mixing Western Swing instrumentation with a steady stream of barroom-ready weepers and novelty tunes, delivered in his distinctively silky baritone. Thompson’s mournful 1952 single, “The Wild Side of Life,” which logged 15 weeks atop the country chart, would change the course of the male-dominated genre by inspiring the Kitty Wells answer song “It Wasn’t God Who Made Honky-Tonk Angels.” His multi-award-winning Brazos Valley Boys Band, which took many of their musical cues from Western Swing legend Bob Wills, emphasized his vocal prowess and song content over excessive instrumentation. Thompson would inspire the character of Bad Blake (played by Oscar winner Jeff Bridges in the 2009 film) in the novel Crazy Heart. Elected to the Country Music Hall of Fame in 1989, Thompson died in 2007. S.B.

Key Tracks: “The Wild Side of Life,” “Rub-a-Dub-Dub,” “The Older the Violin, The Sweeter the Music”

Emmylou Harris 1977 at the Music File Photos 1970's in London, United Kingdom. (Photo by Chris Walter/WireImage)

Emmylou Harris

Country’s quintessential harmony singer and finder of songs, Harris’ profound emotional stamp has distinguished hundreds of records (hers and others’) for decades. “The way people pronounce words and syllables is so important to me – even more important than the parts. It’s a matter of that feel,” Harris told Rolling Stone in 1978 of her vocal contributions. Mentored by and first paired with Gram Parsons, who died in 1973, Harris began a two-decade run with Warner Bros., taking interpretations of hits from Buck Owens (“Together Again”) and Patsy Cline (“Sweet Dreams”) to Number One and making superstars of her Hot Band members, including Rodney Crowell and Ricky Skaggs. She joined Linda Ronstadt and Dolly Parton for the long-gestated Trio LP in 1986 and teamed with producer Daniel Lanois for 1995’s intense, needle-moving Wrecking Ball, a prelude to her growing reliance on her own insightful songwriting. S.B.

Key Tracks: “Boulder to Birmingham,” “Deeper Well”

UNSPECIFIED - JANUARY 01: (AUSTRALIA OUT) Photo of Johnny HORTON; Portrait with a guitar (Photo by GAB Archive/Redferns)

Johnny Horton

Johnny Horton was the early master of the story-song, a medium later popularized by country artists like Johnny Cash and Tom T. Hall. With a penchant for historical tunes, the Texas-raised troubadour told tales of the War of 1812 (“The Battle of New Orleans”) and a World War II navy mission (“Sink the Bismarck”) and sang three songs about the Alaska gold rush during his brief career – he died in a 1960 car accident. More a rockabilly singer than a country artist, Horton nonetheless had an impact on Nashville, especially with his 1958 debut single “Honky Tonk Man,” which Dwight Yoakam covered as his debut single in 1986. But it was “The Battle of New Orleans” with which he is most associated. It’s a marvel of a song, driven by a plinking banjo, a marching beat and Horton’s exhortation to “fire our cannons until the barrel melted down.” J.H.

Key Tracks: “The Battle of New Orleans,” “North to Alaska” 

UNITED STATES - JANUARY 01: NASHVILLE Photo of John ANDERSON (C&W) (Photo by Beth Gwinn/Redferns)

John Anderson

In the wake of the early Eighties country-crossover moment embodied by Urban Cowboy, someone had to drag the music back to its barroom roots, and the Florida-born, Haggard-loving Anderson stepped up. Boosted by Anderson’s voice, which recalled George Jones’ pained baritone, early hits like “Swingin’,” “I Just Came Home to Count the Memories,” and “I’m Just an Old Chunk of Coal” made fiddles and steel guitars cool again in country, and not a moment too soon. Later hits like 1992’s potent “Seminole Wind” – and even parts of his most recent album, 2015’s Goldmine – show Anderson remains a proudly stubborn, beefy-voiced traditionalist. D.B.

Key Tracks: “Wild and Blue,” “Seminole Wind”

UNSPECIFIED - JANUARY 01: (AUSTRALIA OUT) STUDIO Photo of Don GIBSON, - (Photo by GAB Archive/Redferns)

Don Gibson

Regarded for his swooping, moaning vocals and an impressive catalog of skillfully penned tales of heartache and regret, singer-songwriter and so-called “sad poet” Don Gibson notched his first hit in 1956 with “Sweet Dreams,” which seven years later would be the first posthumous hit for Patsy Cline. But it was Gibson’s doubled-sided smash in 1957 that identified him as an ace vocalist and writer: “Oh Lonesome Me” and “I Can’t Stop Loving You.” Both were written on the same day, and with “I Can’t Stop Loving You,” Gibson and producer Chet Atkins created a Countrypolitan classic, a song that would be covered by Ray Charles, Kitty Wells, Elvis Presley, Frank Sinatra, Neil Young and Duke Ellington, among others. After several RCA hits, Gibson moved to Hickory Records and scored with the romantic “Woman (Sensuous Woman).” In 1973, he was inducted into the Nashville Songwriters Hall of Fame, with Country Music Hall of Fame induction following in 2001. Gibson died in 2003 at 75 years old, but “I Can’t Stop Loving You” lives on as a part of the American songbook. S.B.

Key Tracks: “Oh Lonesome Me,” “I Can’t Stop Loving You,” “I’ll Be a Legend in My Time”

(GERMANY OUT) Jim Reeves- 1964 (Photo by ullstein bild/ullstein bild via Getty Images)

Jim Reeves

Initially styled as a honky-tonk troubadour, Texas-born Jim Reeves scored early hits with “Mexican Joe” and the novelty tune “Bimbo” before making an abrupt change that altered the trajectory of country music. For his 1957 single “Four Walls,” Reeves adopted a crooning vocal style that emphasized his resonant baritone and paired it with producer Chet Atkins’ lush, mellow arrangement, creating what may well be the first Countrypolitan record in the process. The gamble was a successful one: “Four Walls” reached the top of the country chart and Number 12 on the pop chart. Reeves would apply this smoothed-out approach for the remainder of his career, scoring his biggest hit with the vibraphone-assisted “He’ll Have to Go” in 1959, but scoring a succession of hits with “Am I Losing You,” “I Know One” and “Adios Amigo,” among others. Reeves’ career was cut tragically short in 1964, when the plane he was piloting crashed after encountering bad weather in Nashville, but his efforts to reach out to the larger world of pop are still echoing well into the present day. J.F.

Key Tracks: “He’ll Have to Go,” “Four Walls”

UNITED KINGDOM - APRIL 01: COUNTRY MUSIC FESTIVAL WEMBLEY Photo of Ronnie MILSAP, Ronnie Milsap performing on stage (Photo by David Redfern/Redferns)

Ronnie Milsap

At Charley Pride’s suggestion, Ronnie Milsap made his way to Nashville and kicked off one of the most astonishing runs of hits in country music history. Blind since birth, Milsap previously performed more straight-up soul and played sessions in Memphis (including on Elvis Presley’s “Kentucky Rain”) before conquering country. As a country performer, he showed incredible versatility as he incorporated touches of soul, blues, doo-wop and rockabilly, all of which helped him become popular as a crossover act in the early Eighties. Beginning with the 1974 release “Pure Love,” Milsap racked up more than 30 country Number Ones, including “(I’d Be) A Legend in My Time” and “Daydreams About Night Things.” Several of these had dual success on the Adult Contemporary chart, the butter-smooth country-soul arrangements on “Smoky Mountain Rain,” “(There’s) No Gettin’ Over Me,” and “I Wouldn’t Have Missed It for the World” proving palatable to a wide range of fans. Milsap continued having chart-topping hits right through the end of the Eighties, when Garth Brooks and Alan Jackson announced themselves to the world and momentarily shifted country back to a more traditional sound. But Milsap, who was inducted into the Country Music Hall of Fame in 2014, created a vital template for any performer – like Lady Antebellum – who understood that country didn’t have to sound like it had just rolled out of a honky-tonk. J.F.

Key Tracks: “Smoky Mountain Rain,” “Daydreams About Night Things,” “(There’s) No Gettin’ Over Me”

Don Williams, U.S. country music singer-songwriter, playing the guitar and singing into a microphone on stage at the Country Music Festival, at Wembley Arena, London, England, Great Britain, in April 1982. (Photo by David Redfern/Redferns/Getty Images)

Don Williams

With his warm, resonant voice and laid-back stage delivery, this tall Texan (nicknamed the “Gentle Giant”) turned mellow country tunes such as “Good Ole Boys Like Me” into enchanting tales akin to refined Southern literature. The first country artist to film a concept music video in 1973, Williams mined gold with songs from Bob McDill (“Amanda”), Townes Van Zandt (“If I Needed You,” with Emmylou Harris) and Danny Flowers (“Tulsa Time”). His own compositions were cut by Johnny Cash (“Down the Road I Go”), Eric Clapton (“We’re All the Way”) and Pete Townshend (“Til the Rivers All Run Dry”). The 1978 CMA Male Vocalist and 2010 Country Music Hall of Fame inductee inspired a fervent international following, performing live until his 2016 retirement. A 2017 tribute LP, Gentle Giants, featured such Williams fans as Alison Krauss, Garth Brooks, Brandy Clark, Jason Isbell and Amanda Shires. S.B.

Key Tracks: “I Believe in You,” “Lord, I Hope This Day Is Good,” “Some Broken Hearts Never Mend” 

UNSPECIFIED - CIRCA 1970: Photo of Keith Whitley Photo by Waring Abbott/Michael Ochs Archives/Getty Images

Keith Whitley

Keith Whitley’s country career was short – only consisting of two albums and a handful of singles during his lifetime – but he has been immortalized as one of the most influential and tragic figures in the genre’s history. Born and raised in Kentucky, Whitley joined bluegrass legend Ralph Stanley’s band as a young man and soon became the group’s lead singer. Beginning his solo career in the early Eighties, he worked his way to critical acclaim and commercial success with the 1988 album Don’t Close Your Eyes, pairing a classic, bluegrass-country vocal with contemporary production. But one year later, the 33-year-old artist died at the height of his artistry, succumbing to the effects of alcohol poisoning. Even so, emotionally complex songs like “Don’t Close Your Eyes,” “When You Say Nothing at All” and “I’m No Stranger to the Rain” have gone on to become canonized as country classics, and Whitley has been cited as an inspiration by artists from Vince Gill to Chris Young. C.P.

Key Tracks: “Don’t Close Your Eyes,” “When You Say Nothing at All”

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