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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.”

Townes Van Zandt during Townes Van Zandt in Concert at the The Last Resort - February 6, 1973 at The Last Resort in Athens, Georgia, United States. (Photo by Tom Hill/WireImage)

Townes Van Zandt

Tom Hill/WireImage

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Townes Van Zandt

Decades before terms like “Americana” were being tossed about, Van Zandt defined that nebulous term, blending country with folk and singing in a bony, prairie-flat voice more at home in coffee houses than in arenas. Like Kristofferson, he was part of a new generation of poetic-soul songwriter that emerged in the Sixties, and he too became best known for inspiring covers – in his case, Willie Nelson and Merle Haggard’s “Pancho and Lefty” and Emmylou Harris and Don Williams’ hit duet on “If I Needed You.” Given his self-destructive streak, it wasn’t surprising when Van Zandt died of a heart attack in 1997 at 52, but his poignant ruminations endure in covers by Steve Earle and Norah Jones, among others. David Browne

Key Tracks: “Waiting Around to Die,” “Fare Thee Well, Miss Carousel” 

UNSPECIFIED - JANUARY 01: Photo of Lynn ANDERSON (Photo by Ron Howard/Redferns)

Lynn Anderson

Ron Howard/Redferns

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Lynn Anderson

The North Dakota-born Lynn Anderson has her mother to thank for launching her country career: mom Liz Anderson wrote Merle Haggard’s breakthrough hit “(My Friends Are Gonna Be) Strangers,” which helped introduce her to the head of her first record label. Anderson also made regular appearances on The Lawrence Welk Show during her teenage years, which helped propel songs like the wistful yet upbeat “If I Kiss You (Will You Go Away)” to the country Top 10. She moved to Nashville in 1970 and a year later she’d managed to top both the country and pop charts with “Rose Garden,” a no-nonsense ode to living in the moment that showcased her brassy delivery. Her string of country hits, which included her cover of the Carpenters’ bubbly “Top of the World” and the saucy “What a Man My Man Is,” continued through the mid Seventies. In the Eighties she returned to the country Top 10 with “You’re Welcome to Tonight,” a duet with smooth vocalist Gary Morris. Her final album Bridges, which features a gospel-tinged version of the dreamy Dobie Gray smash “Drift Away,” came out a month before her death in 2015. M.J.

Key Tracks: “Rose Garden,” “If I Kiss You,” “What a Man My Man Is”

UNSPECIFIED - CIRCA 1970: Photo of Statler Brothers Photo by Michael Ochs Archives/Getty Images

Statler Brothers

Michael Ochs Archives/Getty

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Statler Brothers

Not a family act ­– they got together while singing at church in their shared hometown of Staunton, Virginia – this quartet blended country’s down-home melodicism with gospel’s stirring harmonies and were the backing vocalists for Johnny Cash through the mid-Seventies, all the while scoring hits on their own. The title track of the Statlers’ 1966 debut Flowers on the Wall became a crossover smash, hitting Number Two on the country chart and Number Four on the Hot 100. The song’s absurdist yet heartfelt lyrics, penned by tenor Lee DeWitt, prompted novelist Kurt Vonnegut to dub the group “America’s poets.” The biting 1970 single “Bed of Rose’s,” written by bass singer Harold Reid, took on small-town hypocrisy with a jaunty rhythm; the sweet ode to an audience member “Do You Know You Are My Sunshine” neatly splits the titular question in two. In the early Eighties, the Statlers ­– minus DeWitt, who left the group in 1983 – topped the Hot Country Songs survey with “Elizabeth,” “My Only Love” and “Too Much on My Heart,” all of which were written by new tenor Jimmy Fortune. In the Nineties the group hosted a variety show on the Nashville Network. They split in 2002, although the inclusion of their songs in the film Pulp Fiction and, oddly, the video game Grand Theft Audio: San Andreas has extended their legacy to new generations. M.J.

Key Tracks: “Flowers on the Wall,” “Bed of Rose’s,” “Do You Know You Are My Sunshine?”

LAS VEGAS - MAY 14: Musician Taylor Swift performs onstage during the first ever Academy Of Country Music New Artists' Show Party for a Cause, benefiting the ACM Charitable Fund held at the MGM Grand Ballroom, MGM Grand Conference Center on May 14, 2007 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)

Taylor Swift

Ethan Miller/Getty

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Taylor Swift

It was inevitable that Taylor Swift would leave country music behind for pop – her superstar quality could not be contained by just one genre. As a teenager writing her own songs, Swift ­– born in Pennsylvania, groomed in Nashville – impacted country radio before she was even 18, with “Tim McGraw” a Top 10 hit, and “Our Song” her first country Number One in 2007. By the time she’d invoked the wrath of Kanye West at the 2009 VMAs, she was already playing to a different tune than her peers, and subsequent LPs Fearless and Red led to greater notoriety. Still, her conscious uncoupling from the genre that established her ahead of 2014’s smash 1989 left some wishing she kept one foot in country. “Love you, mean it,” Swift said in a 2014 Rolling Stone cover story, “but this is how it’s going to be.” J.G. 

Key Tracks: “You Belong to Me,” “Tim McGraw”

Alabama (Randy Owen, Teddy Gentry and Jeff Cook), U.S. country music band, pose sitting on stools, circa 1980.. (Photo by David Redfern/Redferns/Getty Images)

Alabama (Randy Owen, Teddy Gentry and Jeff Cook)

David Redfern/Redferns/Getty

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Alabama

In the late 1970s, bands did not make mainstream country music – solo artists did. Bands made dirty, free-loving rock & roll, or maybe bluegrass, but they didn’t (god forbid) mix the two, until Alabama, a trio of friends from Fort Payne, Alabama, who went on to be one of the best-selling acts of all time. Randy Owen, Jeff Cook and Teddy Gentry were so left-field that they were initially rejected from every label in Nashville, ultimately landing on RCA and introducing their style, which blended monster hooks, traditional fiddle and Southern roots, in a way that left Music Row blindsided and pearl-clutching – but then begging for more. Forty-three Number One singles later, Alabama made a new sort of musical fusion possible, one that opened up the door for everyone from Eli Young Band to Old Crow Medicine Show, whose version of Alabama’s “Dixieland Delight” is a new classic. M.M.

Key Tracks: “Mountain Music,” “Song of the South,” “I’m in a Hurry (and Don’t Know Why)” 

LONDON, ENGLAND - JULY 23: Rosanne Cash performs at the Union Chapel on July 23, 2015 in London, United Kingdom. (Photo by Robin Little/Redferns)

Roseanne Cash

Robin Little/Redferns

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Rosanne Cash

Johnny Cash’s daughter fused literate, vulnerable subject matter with muscular new wave-tinged production during her mainstream country heyday, resulting in a spectacular string of LPs beginning with 1980’s Right or Wrong through 1987’s King’s Record Shop. With her post-divorce (from producer Rodney Crowell) second act she dissected heartbreak down to its most minute detail, and plumbed extraordinary depths after losing her parents – and stepmother, June Carter Cash – with 2006’s grief-stricken Black Cadillac and 2014’s colorful Southern travelogue The River & The Thread, both recorded with current husband-collaborator John Leventhal. “Like any person in their twenties,” she told Rolling Stone in 2014, “I needed to get away from my parents to find out who I was. But in your thirties, you start appreciating who your parents are, and by your forties, you say, ‘They know a couple of things – maybe I should be friends with them.'” S.B.

Key Tracks: “Seven Year Ache,” “Paralyzed,” “World of Strange Design”

UNITED KINGDOM - JANUARY 01: WEMBLEY ARENA Photo of Patty LOVELESS (Photo by David Redfern/Redferns)

Patty Loveless

David Redfern/Redferns

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Patty Loveless

When George Jones died, Patty Loveless sang (with Vince Gill) at his funeral. That was perfect. Loveless’ breakthrough single was a version of Jones’ “If My Heart Had Windows,” and the legend’s own final hit was a duet with Loveless, “You Don’t Seem to Miss Me.” From the late Eighties through most of the Nineties, Loveless married her roots in Appalachian bluegrass to Jones’ in-the-moment honky-tonk countrypolitan, and the result was a string of hits that modernized the old sounds. Her ballads (“Don’t Toss Us Away,” “Lonely Too Long”) made grownups tear up while her fast ones (“Chains,” “I Try to Think about Elvis”) found a solution for tears on the dancefloor and in singing along. These days Loveless can’t buy a hit. But that doesn’t mean George Jones’ greatest acolyte isn’t still the best country singer alive. David Cantwell

Key Tracks: “Don’t Toss Us Away,” “You Don’t Seem to Miss Me,” “I Try to Think About Elvis” 

TARRYTOWN, NY - JUNE 22: Country singer Marty Stuart on his tour bus at the Westchester Premiere Theater in Tarrytown, New York on June 22, 1992. (Photo by Waring Abbott/Getty Images)

Marty Stuart

Waring Abbott/Getty

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Marty Stuart

A musician’s musician, Stuart logged more than a decade as a sideman for the titans of twang – including Johnny Cash, Doc Watson and Lester Flatt – before launching his solo career. Mainstream success arrived during the late Eighties, with Stuart building his fanbase not only on the strength of his voice, but his hotshot guitar playing, too. Now 45 years into an acclaimed career, he’s built a resume as towering as his notoriously rooster-like hairdo, collaborating with Tom Petty & the Heartbreakers one minute and hosting his own cult-favorite TV program, The Marty Stuart Show, the next. On his newest release, Way Out West, he connects the dots between surf music, California country and spaghetti western soundtracks, fashioning a sound as bold and broad as his own history. A.L.

Key Tracks: “This One’s Gonna Hurt You (For a Long, Long Time),” “Way Out West”

Photo of ASLEEP AT THE WHEEL; L-R (back): Ray Benson; (middle): Leroy Preston, Danny Levin, Chris O'Connell, Scott Hennige, Floyd Domino, Tony Garnier; (front): Lucky Oceans, Bill Mabry, Link Davis Jr posed, (Photo by Charlie Gillett Collection/Redferns)

Asleep At The Wheel

Charlie Gillett Collection/Redferns

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Asleep at the Wheel

Ray Benson has been preaching the gospel of Western swing for more than 45 years, and given his imposing 6-foot 7-inch frame, his message has been hard to ignore. Of course, there’s also the music delivered by his consistently stellar band Asleep at the Wheel, a group of rotating members that faithfully re-creates one of country’s most thrilling subgenres. Benson’s admiration for Bob Wills (the Wheel have recorded several tributes to the Western swing legend) helped preserve the form in an era where it might otherwise have been forgotten. Despite only scoring one significant hit in “The Letter That Johnny Walker Read,” the Wheel have notched Grammys (including one for 2009’s Willie Nelson collab Willie and the Wheel) and played Austin City Limits more than any other artist, a fact helped by being one of country’s great live ensembles. J.G.

Key Tracks: “The Letter That Johnny Walker Read,” “Miles and Miles of Texas”

Nashville singer Lee Ann Womack performing on stage at The Nobel Peace Prize Concert 2000 in Oslo Spektrum in Oslo, Norway at 7:00 pm on Monday 11 December. The event airs in the US on Fox Family Channel on Tues, Dec. 19 at 8:00 pm ET/PT. photo by Gabe Palacio/ImageDirect

Lee Ann Womack

Gabe Palacio/ImageDirect

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Lee Ann Womack

“I Hope You Dance” will forever be the song that casual fans will associate with Lee Ann Womack, but there’s a lot more to the Texas native than that adult contemporary crossover hit. She got her footing in Nashville as a songwriter during the Nineties, including writing Ricky Skaggs’ “I Don’t Remember Forgetting.” Her self-titled debut followed in 1997, spawning her first hit, “The Fool,” but that was nothing compared to the success of “I Hope You Dance” three years later. Womack would never reach those heights again, which may be just as well, as she’s since returned to her more traditionalist roots on The Way I’m Livin’ in 2014. “I’m more drawn to songs written at 2 a.m. on the back of the bus than I am the songs written by four or five people at a 10 a.m. appointment,” she told Rolling Stone at the time. J.G.

Key Tracks: “The Fool,” “I Hope You Dance,” “I May Hate Myself in the Morning”

Photo of Merle Travis (Photo by Michael Ochs Archives/Getty Images)

Merle Travis

Michael Ochs Archives/Getty

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Merle Travis

Kentucky-born Merle Travis was one of the first guitar heroes. His unconventional style of playing, especially on the electric guitar, influenced no less than Chet Atkins, with whom he recorded the Grammy-winning Atkins-Travis Travelling Show album in 1974. But Travis was more than just a player; he also wrote, recorded and sang a number of hits, including “Sixteen Tons,” which Tennessee Ernie Ford turned into his signature in 1955. “Smoke! Smoke! Smoke! (That Cigarette)” was another Travis composition, taken to Number One by its co-writer Tex Williams, while the cheekily titled “So Round, So Firm, So Fully Packed” also employed smoking metaphors – to describe a woman. Travis was inducted into the Country Music Hall of Fame in 1977, where the solid-body electric guitar he designed – a precursor to the Fender Telecaster – is on display today. J.H.

Key Tracks: “Sixteen Tons,” “So Round, So Firm, So Fully Packed”

Photo of Jessi Colter (Photo by Michael Ochs Archives/Getty Images)

Jessi Colter

Michael Ochs Archives/Getty

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Jessi Colter

To the uninitiated, she’s still Mrs. Waylon Jennings, having married the country legend in 1969, one year after finalizing her divorce from guitar hero Duane Eddy. Colter’s musical legend extends far beyond her personal life, though. A force on the country charts during the second half of the Seventies, she wrote her own songs and called her own shots, breaking up the Outlaw country boys’ club with a frank, fiery female perspective. Pulling equally from roadhouse roots-rock, timeless country and the contemporary trends, she laid the groundwork for later generations of western women, with Miranda Lambert and Kacey Musgraves both carrying her torch during the 21st century. A.L.

Key Tracks: “I’m Not Lisa,” “Storms Never Last”

Portrait of country musician Dwight Yoakum at Farm Aid, Ames, Iowa, April 4, 1990. (Photo by Paul Natkin/Getty Images)

Dwight Yoakum

Paul Natkin/Getty

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Dwight Yoakam

When he emerged in the Eighties, Yoakam looked and sounded like a true New Traditionalist – a new-generation honky-tonker – from his high-and-lonesome twang to his love of Hank, Haggard and Buck. But beneath that ubiquitous hat was a singer and writer who wasn’t afraid to push the music’s boundaries, and before long, Yoakam was mixing it up with rockabilly shuffles, south-of-the-border ballads, Beatles and Queen covers, and skinny-jean stage moves that made the ladies scream. Yoakam was able to adhere to country’s roots while drawing rock fans who had barely paid any attention to the genre, which was no easy feat. He also made his name as an actor, but in music, Yoakam truly took the music back to the future. D.B.

Key Tracks: “Guitars, Cadillacs,” “Fast As You,” “I Sang Dixie” 

Vern Gosdin (1934 - 2009) performing in Chicago, Illinois, April 28, 1977. (Photo by Paul Natkin/Getty Images)

Vern Gosdin

Paul Natkin/Getty

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Vern Gosdin

With elderly wisdom etched in eternal heartbreak, the largely doleful Vern Gosdin canon earned him the nickname “The Voice,” often out-Jones-ing George, to whom he would inevitably be compared. A member of the early Sixties bluegrass group the Hillmen – with mandolin player and future Byrds and Flying Burrito Brothers member Chris Hillman – Gosdin would become one of the Eighties’ most consistent hitmakers, with a few uptempo tunes (“Set ‘Em Up Joe,” “I Can Tell By the Way You Dance”) but an even larger number of heart-wrenching ballads, including “Is It Raining at Your House” (later covered by Brad Paisley) and the 1989 CMA Song of the Year, “Chiseled in Stone,” co-written with Max D. Barnes. In 1997, George Strait had a hit with the Gosdin-Mark Wright tune “Today My World Slipped Away” and in 2011 Willie Nelson cut the Gosdin-Barnes gem “That Just About Does It.” S.B.

Key Tracks: “Chiseled in Stone,” “Is It Raining At Your House,” “Do You Believe Me Now” 

American country music singer Connie Smith in a posed portrait, 1996. (Photo by Beth Gwinn/Redferns/Getty Images)

Connie Smith

Beth Gwinn/Redferns/Getty

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Connie Smith

Dubbed “the Rolls Royce of female country vocalists” by Grand Ole Opry announcer Eddie Stubbs for the overwhelming power and elegance of her rafter-rattling instrument, Connie Smith made history in 1964 with the Bill Anderson-penned “Once a Day.” The first female country artist with a Number One debut single, her subsequent hits melded Nashville Sound production and exquisite songcraft with effortlessly plaintive vocals, whether she’s singing honky-tonk weepers or soul-affirming gospel. As Dolly Parton once said, “There’s really only three female singers in the world: Streisand, Ronstadt and Connie Smith. The rest of us are only pretending.” Her most recent LP, Long Line of Heartaches, produced by husband Marty Stuart, was issued just prior to her 2012 election into the Country Music Hall of Fame. S.B.

Key Tracks: “Nobody But a Fool (Would Love You),” “Burning a Hole in My Mind,” “The Hurtin’s All Over”

Photo of Guy CLARK; (Photo by David Redfern/Redferns)

Guy Clark

David Redfern/Redferns

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Guy Clark

The wind had its way with her hair, and the blues had a way with her smile,” sang Guy Clark on “She Ain’t Going Nowhere,” a track off of his now iconic debut, Old No. 1. Clark always thought of himself as a prose man, but lyrics like that – a potent cocktail of nostalgia, metaphor and emotion – were often as poetic as they come. Born in Monahans, Texas, Clark – along with the likes of Townes Van Zandt and Rodney Crowell – shaped a place in Nashville for country music that was based more around the folk tradition than marketability, becoming one of the genre’s most beloved and respected writers. Ricky Skaggs and Vince Gill took his songs to Number One, but Clark stayed true to his craftsman soul until the very end, finally winning a Grammy for his last LP, My Favorite Picture of You. M.M.

Key Tracks: “L.A. Freeway,” “Desperados Waiting for a Train,” “Randall Knife” 

(Original Caption) : 1978- Picture shows country singer, Tanya Tucker, holding a guitar to the side and wearing a black leather suit. (Photo by Lynn Goldsmith/Corbis/VCG via Getty Images)

Tanya Tucker

Lynn Goldsmith/Corbis/VCG via Getty

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Tanya Tucker

Tanya Tucker wasn’t even old enough to get a driver’s license when she recorded “Delta Dawn,” but she sang it with the confidence of someone twice her age. That gritty vocal timbre, coupled with the possibly-too-mature subject matter of her songs (like “Would You Lay With Me [In a Field of Stone])”, made the young Seminole, Texas, native a star and an archetype for the tough-talking, rebellious female performers who followed in her wake. She could rock out with ease – check out her cover of “Not Fade Away” on TNT – but was equally comfortable selling the drama of a good ballad. Drinking and substance abuse issues threatened to derail Tucker’s career in the early 1980s, but she enjoyed an impressive second act with a softer pop-country sound in the late Eighties, scoring a long string of Top 10 hits including Number Ones “Strong Enough to Bend” and “If It Don’t Come Easy.” She hasn’t been as active in the last decade, but in fairness she’d already cranked out more hits by 20 than most people do in a lifetime. J.F.

Key Tracks: “Delta Dawn,” “Would You Lay With Me (In a Field of Stone),” “Texas (When I Die)”

UNSPECIFIED - CIRCA 1970: Photo of Roy Acuff Photo by Michael Ochs Archives/Getty Images

Roy Acuff

Michael Ochs Archives/Getty

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Roy Acuff

Country music as we know it starts with Roy Acuff. The fiddler with a quintessentially spare singing style wasn’t called “The King of Country Music” for nothing: Acuff, more than anyone, had the savvy to see the business potential in country music. During the late Thirties and Forties, when his songs like “The Great Speckled Bird” and “The Wreck on the Highway” saw him rule the charts, the first-ever living inductee to the Country Music Hall of Fame helped transform the Grand Ole Opry from country bumpkin revue into a bonafide showcase. Most important, however, was Acuff’s vision in founding the Acuff-Rose publishing house with Fred Rose, which made Nashville into a publishing hotspot and ensured that Music City would forever be the cradle of country music. J.G.

Key Tracks: “Great Speckled Bird,” “The Wreck on the Highway”

SOLANA BEACH, CA - MARCH 08: Singer/songwriter Billy Joe Shaver performs on stage at Belly Up Tavern on March 8, 2015 in Solana Beach, California. (Photo by Daniel Knighton/FilmMagic)

Billy Joe Shaver

Daniel Knighton/FilmMagic

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Billy Joe Shaver

Billy Joe Shaver is ground zero for outlaw country songwriters. A millworker from Corsicana, Texas (he lost two fingers on the job), Shaver was the man behind some of the Seventies’ most memorable songs, starting with Waylon Jennings’ seminal outlaw LP, 1973’s Honky Tonk Heroes, most which was written by Shaver. His own debut, Old Five and Dimers Like Me, released the same year and produced by Kris Kristofferson, is a country classic in its own right, but writing the songs has always taken priority over playing them for Shaver. “The song is the cheapest psychiatrist there is. I pretty much need one all the time,” he said in 2014. J.G.

Key Tracks: “Old Five and Dimers Like Me,” “Honky Tonk Heroes,” “Willie the Wandering Gypsy and Me”

UNSPECIFIED - JANUARY 01: Photo of Marty ROBBINS (Photo by David Redfern/Redferns)

Marty Robbins

David Redfern/Redferns

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Marty Robbins

Few voices in country music were as instantly recognizable as Marty Robbins, and few artists took as many chances as the “El Paso” singer. Rock & roll, calypso, blues – everything was fair game for Robbins, who even moonlighted as a NASCAR driver when simply scoring country and pop hits became too easy. And Robbins scored plenty of those, starting in earnest with his doo-wop ditty “A White Sport Coat and a Pink Carnation” in 1957, one of 17 Number One singles he would record. The Arizona native’s rich croon was perfect for swinging love songs, yet he made his most enduring mark as the master of murder ballads, 1959’s “El Paso” – a Number One pop hit, as well – being the pinnacle of the form. Robbins, who suffered multiple heart attacks over the years, would die from one in 1983, at the age of 57. J.G.

Key Tracks: “El Paso,” “Don’t Worry,” “Devil Woman”

UNSPECIFIED - CIRCA 1970: Photo of Faron Young Photo by Michael Ochs Archives/Getty Images

Faron Young

Michael Ochs Archives/Getty

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Faron Young

While a singer on the Louisiana Hayride radio show ­– where Elvis Presley received one of his early boosts ­– Faron Young sang alongside Webb Pierce, developing a country croon that evoked that of Hank Williams. But Young, a Shreveport, Louisiana, native was his own vocalist, especially as he entered the Sixties with a sterling version of Willie Nelson’s “Hello Walls.” He topped the country chart with the song, and entered the Top 20 on the pop survey. A member of the Grand Ole Opry, Young was also an actor, appearing in a number of Westerns. Later in life, he’d capitalize on Nashville’s role as a music-biz hotbed, launching a trade paper and running a booking agency. Best of all: he recorded the most badass titled song of the Fifties: the 1955 Number One “Live Fast, Love Hard, Die Young.” J.H.

Key Tracks: “Live Fast, Love Hard, Die Young,” “Hello Walls”

C/W musician Vince Gill performing on stage of Grand Ole Opry. (Photo by William F. Campbell/The LIFE Images Collection/Getty Images)

Vince Gill

William F. Campbell/The LIFE Images Collection/Getty

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Vince Gill

The winner of more Grammys than any other male country artist – 21, as of 2017 – Vince Gill could have called it a career years ago. But that’s not this Okie’s style. He’s never been in it for the glory; rather, Gill is a slave to the music. Every Monday night, the guitarslinger and pristine vocalist can be found onstage at a Nashville club with Western swing group the Time Jumpers, playing not for his cut of the $20 cover charge, but for the joy. It’s such pure motivation that makes Gill one of country’s most valuable assets. A vocal champion of traditional country – he emotionally challenged today’s bravado-spouting artists to let him “hear how country” they are during his 2012 ACM Honors speech – Gill expertly mixes trad-country with a pop sensibility on albums like the 2006 Grammy-winning opus These Days and last year’s Down to My Last Bad Habit. And his guitar playing has landed him on records by artists like Alice Cooper and onstage with Eric Clapton. Soon, he’ll join the Eagles for two weekends of concerts, refusing to slow down, even as he just turned 60. “My body tells me I’m not the same guy, but I don’t see an old guy in the mirror,” Gill told Rolling Stone Country in 2014. “I still see that 22-year-old kid riding buses and playing the guitar and singing. I want to get as old as I can.” J.H.

Key Track: “When I Call Your Name,” “Liza Jane,” “Go Rest High on That Mountain”

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

Webb Pierce

Michael Ochs Archives/Getty

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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

Michael Ochs Archives/Getty

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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

Michael Ochs Archives/Getty

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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

Chris Walter/WireImage

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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

GAB Archive/Redferns

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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

Beth Gwinn/Redferns

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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

GAB Archive/Redferns

55

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

ullstein bild/ullstein bild via Getty

54

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”