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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.”

UNITED KINGDOM - JANUARY 01: Photo of Hank WILLIAMS Jnr (Photo by David Redfern/Redferns)

Hank Williams Jr.

David Redfern/Redferns

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Hank Williams Jr.

Following in the footsteps of a famous father – possibly even the most famous of them all – is more than most artists could handle, but Hank Williams Jr. parlayed that burden into being one country’s most popular artists during the Eighties. It didn’t come easily – “Bocephus” spent years in Hank Sr.’s long shadow before a near fatal mountain-climbing accident inspired a reinvention. Rebellious, rock-influenced hits like “Family Tradition” and “All My Rowdy Friends Are Coming Over Tonight” catapulted him all the way to a primetime spot on Monday Night Football, but his Confederate flag-waving renegade streak hasn’t always been warmly received: He was unceremoniously dropped by MNF after comparing President Obama to Hitler in 2011 (he was recently rehired for the gig). Despite all his controversies, Williams remains a touchstone for today’s own rowdy crop of artists, from Justin Moore to Kid Rock. Wisely, he’s also tried to place music over politics. “I don’t give a shit about the election,” he declared to Rolling Stone in 2016, “I’ve got a smash CD coming out!” J.G.

Key Tracks: “A Country Boy Can Survive,” “Family Tradition,” “Whiskey Bent and Hellbound'”

UNITED KINGDOM - JANUARY 01: WEMBLEY EMPIRE POOL Photo of Kenny ROGERS, Kenny Rogers performing on stage (Photo by David Redfern/Redferns)

Kenny Rogers

David Redfern/Redferns

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Kenny Rogers

“The Gambler” himself has worn a number of hats through the course of a career that stretches back more than five decades, but none has fit more comfortably for Kenny Rogers than that of a country hitmaker. Not that the Houston native was always a country singer: his earliest forays, and first (minor) hits, came as the singer of psychedelic rock band the First Edition in the late Sixties. But Rogers’ destiny was to be a solo superstar, and once “Lucille” propelled his golden rasp to the top of the country charts he never looked back. Rogers would sell over 100 million albums and star in countless TV specials, and always seemed to find himself sharing the studio with his peers, duetting with everyone from Dolly Parton (“Islands in the Stream”) to Lionel Richie (“Lady”). “Some of the highlights of my life were duets,” he told Rolling Stone in 2014. “I sing better on duets than I do by myself.” J.G.

Key Tracks: “Lucille,” “The Gambler,” “Coward of the County”

"Tennessee" Ernie Ford is shown smiling and wearing a suit in close up shot.

Tennessee Ernie Ford

Bettmann/Getty

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Tennessee Ernie Ford

A versatile, deep-voiced performer, Tennessee Ernie Ford became the model for future generations of multi-faceted country entertainers, from Johnny Cash to Dolly Parton. The Bristol, Tennessee, native was once a golden-voiced radio announcer whose catchphrase earned him the nickname “The Ol’ Pea-Picker,” but quickly moved into a long, fruitful recording career that expertly straddled different worlds. Most notably, he enjoyed tremendous crossover success with the chilling – yet irresistible – workingman’s anthem “Sixteen Tons,” originally penned by Merle Travis and, to a lesser degree, “The Ballad of Davy Crockett.” Ford’s charismatic personality and ability to fit his voice to many different styles of music meant he was able to easily shift away from traditional honky-tonk to more pop-oriented material as well as record gospel LPs like the top-selling Hymns, all while maintaining high visibility as a primetime television host through the Sixties. He was inducted into the Country Music Hall of Fame in 1990, shortly before his death in 1991 – one of country’s all-time great entertainers and personalities. J.F.

Key Tracks: “Sixteen Tons,” “The Ballad of Davy Crockett,” “I’ll Never Be Free”

UNSPECIFIED - CIRCA 1970: Photo of Mel Tillis Photo by Michael Ochs Archives/Getty Images

Mel Tillis

Michael Ochs Archives/Getty

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Mel Tillis

Mel Tillis is one of country’s great ambassadors. From his stint in the cast of The Porter Wagoner Show to co-starring film roles with Burt Reynolds and his theater in Branson, Missouri, the Stutterin’ Boy (as he titled his memoir) has used an inviting baritone and comic M-M-Mel stage presence to take country worldwide. He’s garnered 35 Top Ten country hits across three decades, too, but it’s his writing that’s mattered most. The hits he wrote for himself (“Commercial Affection”) and for the Hall of Fame likes of Bobby Bare (“Detroit City”), Charley Pride (“The Snakes Crawl at Night”), Webb Pierce (“I Ain’t Never”) Waylon Jennings (“Mental Revenge”), and Kenny Rogers’s First Edition (“Ruby, Don’t Take Your Love to Town”), among others, is a playlist of incomparably pining paranoia and puts Mel Tillis on the short list of country’s songwriting best. D.C.

Key Tracks: “Commercial
Affection,” “I Ain’t Never,” “Who’s Lisa?”  

UNSPECIFIED - CIRCA 1970: Photo of Gary Stewart Photo by Michael Ochs Archives/Getty Images

Gary Stewart

Michael Ochs Archives/Getty

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Gary Stewart

Hank Williams and Waylon Jennings owned two of the most identifiable voices in the genre, but there was no more “country” voice than that of Gary Stewart. Possessing a quavering, cracking tenor, the Kentucky-born, Florida-reared singer could sustain vibrato like no other, stretching out notes in a way that rivaled George Jones. Listen to his 1975 Number One “She’s Actin’ Single (I’m Drinkin’ Doubles),” which features vocal runs as woozy as the song’s brilliant title. Vices were a frequent subject of Stewart’s songs, from drinking and cheating to drinking again. The alcoholic’s anthem “Drinkin’ Thing,” the adultery tale “Out of Hand” and, another boozer, “Empty Glass” were all windows into Stewart’s own tortured soul. He tragically took his own life in 2003, following the death of his wife. Today, he remains an underappreciated figure, but to those in the know, there is none better. J.H.

Key Tracks: “She’s Actin’ Single (I’m Drinkin’ Doubles),” “Out of Hand”

DUBLIN, IRELAND - SEPTEMBER 18: Muscial group the Dixie Chicks perform live on stage at The Point Theatre September 18, 2003 in Dublin, Ireland. (Photo by ShowBizIreland.com/Getty Images)

Dixie Chicks

ShowBizIreland.com/Getty

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Dixie Chicks

Women have never exactly had it easy in country music, but there was a stretch in the mid-to-late Nineties where the scales seemed to temporarily balance. Out of that glorious period came one of the greatest vocal groups ever to hit the stage, in the form of three young Texas natives. Shedding their earlier Western swing band configuration, badass instrumentalist sisters Martie Erwin Maguire and Emily Erwin Robison, along with powerhouse singer Natalie Maines, set about dominating the country airwaves with their diamond-certified album Wide Open Spaces. It wasn’t a one-off, either: the follow-up Fly sold over 10 million as well, producing indelible, harmony-laden hits like “Cowboy Take Me Away” and the controversial, darkly comic abuse saga “Goodbye Earl.” The 2001 release Home reasserted their position as roots musicians of the highest order before their country radio career evaporated in the wake of Maines’ 2003 remarks about President George W. Bush. They never backed down, though, releasing the more rock-tinged Taking the Long Way with confrontational lead single “Not Ready to Make Nice” and the harrowing documentary Shut Up and Sing in 2006. A full decade later, they’re still just as relevant, flashing Donald Trump’s picture among a group of serial abusers for tour renditions of “Goodbye Earl,” and pretty much owning the 2016 CMA Awards by performing “Daddy Lessons” with Beyonce. Jury’s out on new recordings, though. “There’s not being inspired, but there’s also just not having the life to facilitate that right now,” Maines told Rolling Stone in 2013. “We have nine kids between the three of us.” J.F.

Key Tracks: “Cowboy Take Me Away,” “Long Time Gone,” “Not Ready to Make Nice”

American country music singer Porter Wagoner (1927 - 2007) performing, circa 1960. (Photo by Silver Screen Collection/Getty Images)

Porter Wagoner

Silver Screen Collection/Getty

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Porter Wagoner

A true country-music showman, Porter Wagoner exuded an otherworldly air, thanks in part to his dazzling Western suits. For Wagoner, born in Missouri in 1927, performance was an art, both on record and on the stage. Which is why he was such a natural hosting his own syndicated variety show, a series that ran a remarkable 19 years. It was there that Wagoner put the spotlight on Dolly Parton, introducing her to viewers around the country. They’d go on to cut a series of duets together, including the Number One “Please Don’t Stop Loving Me,” but Wagoner was very much his own artist. His songs “Green, Green Grass of Home” and “The Carroll County Accident” were famous for their last-verse twists – “Carroll County Accident” in particular, the CMA’s Song of the Year in 1969, was a stunner, detailing an illicit romance that is nearly revealed in the aftermath of a wreck on the highway. Wagoner remained a mainstay at the Grand Ole Opry, and in 2008 released his final album, Wagonmaster, produced by Marty Stuart. J.H.

Key Track: “Green, Green Grass of Home,” “The Carroll County Accident”

UNSPECIFIED - JANUARY 01: (AUSTRALIA OUT) Photo of Bobby BARE; Portrait (Photo by GAB Archive/Redferns)

Bobby Bare

GAB Archive/Redferns

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Bobby Bare

A progressive artist during a conservative era, Bobby Bare broadened the horizons of country music throughout the Sixties and Seventies, from his early Top 40 single “Shame on Me” – one of the first country singles to incorporate a horn section – to his left-of-center collaborations with novelty songwriter and weirdo poet Shel Silverstein. He rarely wrote his own hits, focusing instead on a unique, conversational delivery that often moved between speaking and singing. Bare picked his material wisely, too, becoming one of the first stars to record songs by Tom T. Hall, Billy Joe Shaver and Kris Kristofferson. Today, at 82, he’s still making music, releasing the new LP Things Change this year. A.L.

Key Tracks: “(Margie’s at) the Lincoln Park Inn,” “Detroit City”

NASHVILLE, TN - 1954: Country singer Kitty Wells poses for a portrait with an acoustic guitar in 1954 in Nashville, Tennessee. (Photo by Michael Ochs Archives/Getty Images)

Kitty Wells

Michael Ochs Archives/Getty

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Kitty Wells

A feminist trailbreaker, Kitty Wells became the first woman to top the country charts with her 1952 hit “It Wasn’t God Who Made Honky Tonk Angels,” a rejoinder to Hank Thompson’s “The Wild Side of Life” so honest in its depiction of what causes “a good woman to go wrong” it was banned by the Grand Ole Opry. Wells started singing in her teens but didn’t find success until her early 30s, employing her twangy, no-frills voice to convey a spirited independence that drove home real-talking hits like “Will Your Lawyer Talk to God” and “The White Circle On My Finger.” (She was actually happily married to singer-songwriter Johnnie Wright for 74 years). Statements from Loretta Lynn’s “The Pill” to Beyonce’s “Daddy Lessons” are hard to imagine without her signal example. “She was my hero,” Loretta Lynn said when Wells passed away in 2012. “If I had never heard of Kitty Wells, I don’t think I would have been a singer myself. I wanted to sound just like her, but as far as I am concerned, no one will ever be as great as Kitty Wells.” Jon Dolan

Key Tracks: “It Wasn’t God Who Made Honky Tonk Angels,” “Making Believe”

UNSPECIFIED - JANUARY 01: Photo of Charlie RICH (Photo by David Redfern/Redferns)

Charlie Rich

David Redfern/Redferns

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Charlie Rich

Rich, who died in 1995, was best known to country fans for massive Seventies hits like “Behind Closed Doors” and “The Most Beautiful Girl,” which blended his dapper piano and ingrained-wood voice with Billy Sherrill’s Countrypolitan arrangements. (He’s also remembered for a singularly rebellious act: Tasked with announcing the Entertainer of the Year at the CMA Awards in 1975, Rich set the card afire as he named winner John Denver). But as his records before and after showed (Rich started his career at Sun Records in the Fifties), Rich was one of the country’s greatest no-boundary artists, genre-hopping from honky-tonk and ballads to standards, jazz, R&B, gospel, even the random novelty hit. “Life’s Little Ups and Downs” is one of country’s most moving depictions of a couple coping with hard financial times. D.B.

Key Tracks: “The Most Beautiful Girl,” “Behind Closed Doors”

UNSPECIFIED - CIRCA 1970: Photo of Snow Hank Photo by Michael Ochs Archives/Getty Images

Hank Snow

Michael Ochs Archives/Getty

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Hank Snow

Snow
came to his songs of the open road – “I’m Movin’ On,” “The
Golden Rocket,” “I’ve Been Everywhere” – from experience: at age
12 he fled an abusive stepfather and spent the next four years working on a
fishing boat. Born in Nova Scotia, his life was changed by the traveling songs
of Jimmie Rodgers. “I first heard Jimmie Rodgers when I was very young, I
was in my teens,” he remembered. “‘Moonlight and Skies’ – and I
became an ardent fan at that minute. I either had to duplicate Jimmie Rodgers’
success before I died, or bust.” He signed to RCA, the same label as
Rodgers, in 1936, and had his first hits in Canada before cracking the U.S.
market in May of 1950 with “I’m Movin’ On,” a song that blended
acoustic picking and chrome-plated pedal steel into a celebration of freedom
and mobility that spent a record-setting 21 weeks at Number One (Ray Charles
made it a both a pop and R&B hit in 1959, and the Rolling Stones gave it a
frantic live update in 1965). Though he was an early supporter of Elvis Presley
and experimented with Latin rhythms and Hawaiian music in songs like
“Rhumba Boogie,” Snow was a guardian of country twang and tradition
in hits like “(Now and Then) There’s a Fool Such as I” and “Ninety
Miles Hour (Down a Dead End Street)” – even his last big hit, “Hello
Love” in 1974, was a down-home throwback, featured the sort of picking he’d
heard on the Rodgers songs that first inspired him. Joe Levy

Key Tracks: “I’ve Been Everywhere,” “(Now and Then) There’s a Fool Such as I”

LOS ANGELES - CIRCA 1971: Singer/songwriter Gram Parsons poses for a portrait session wearing a t-shirt advertising his band Flying Burrito Bros. sitting on the hood of a Cadillac at Burrito King restaurant in circa 1971 in Los Angeles, California. (Photo by Ginny Winn/Michael Ochs Archives/Getty Images)

Gram Parsons

Ginny Winn/Michael Ochs Archives/Getty

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Gram Parsons

On Sweetheart of the Rodeo, Gram Parsons joined the Byrds to officiate a shotgun wedding between straight country and hippie folk-rock, a marriage he furthered in a cannabis-leaf-patterned Nudie suit with the Flying Burrito Brothers. His songwriting continued to shine over two solo LPs, launching the career of a young Emmylou Harris and influencing a generation of genre-blending musicians, including pal Keith Richards. Parsons died in 1973 at age 26, and never had a hit, but he remains an icon of individualism in a conservative genre. And that fragile tenor is still one of the most moving voices in the canon. Will Hermes

Key Tracks: “Return of the Grievous Angel,” “In My Time of Darkness”

Musician John Prine on stage, circa 1970-1975. (Photo by Tony Russell/Redferns/Getty Images)

John Prine

Tony Russell/Redferns/Getty

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John Prine

In many ways, John Prine was Americana before it had a name. Like Bob Dylan, but more country, like Johnny Cash, but more folk, Prine defied odds by existing nowhere and everywhere and by becoming the master of the sharp, witty phrase that can conjure up tears and laughter at the same time. Born in Illinois, Prine was discovered by Kris Kristofferson, compared to Proust by Dylan and became the subject of a song by Kacey Musgraves. His lyrics tell stories, but they illuminated reality, too: with a nasal rasp and commanding fingerpicking, he finds the moments to sing about that no one else would notice. “How the hell can a person go to work in the morning, and come home in the evening and have nothing to say,” he asked in “Angel From Montgomery,” off his self-titled LP. His work traces the exploits of youth, the limits of aging and the most crooked corners of human nature, all while cracking an illegal smile. “We hold him up as our Hank Williams,” Todd Snider told Rolling Stone. M.M.

Key Tracks: “Sam Stone,” “In Spite of Ourselves,” “Angel from Montgomery” 

UNSPECIFIED - JANUARY 01: (AUSTRALIA OUT) Photo of Jerry REED; posed (Photo by GAB Archive/Redferns)

Jerry Reed

GAB Archive/Redferns

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Jerry Reed

Jerry Reed, the Chuck Berry-adoring wild man and back-slapping prototype good ol’ boy who’ll be inducted posthumously into the Country Music Hall of Fame this fall, could do it all. Reed was a first-call guitarist, playing in the studio behind everyone from Elvis Presley (for his own “Guitar Man” and “U.S. Male”) to Bobby Bare and Merle Haggard (that’s his acoustic part overdubbed on “Okie from Muskogee”), and cutting a trio of pickers paradise albums with no less than Chet Atkins. He was a top-notch songwriter, too, capable of down-to-earth, down-on-his-luck tall tales like his own greatest chart success “When You’re Hot, You’re Hot,” honky-tonk sing-alongs like Porter Wagoner’s “Misery Loves Company,” and Johnny Cash’s wet-eyed anthem “Thing Called Love.” But his madcap masterpiece was 1970’s “Amos Moses,” which just might be country radio’s funniest-ever two-and-half minutes – and maybe its funkiest, too. D.C.

Key Tracks: “Amos Moses,” “East Bound and Down,” “Guitar Man”

Reba McEntire on 8/3/95 in Chicago, Il. (Photo by Paul Natkin/WireImage)

Reba McEntire

Paul Natkin/WireImage

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Reba McEntire

Country artists who don’t require a last name are in rarified air, and Reba is atop that list in the modern era. Ms. McEntire has become a brand unto herself, a force in television, film and on Broadway in addition to being one of country music’s most recognizable figures. Her glowing, versatile voice helped establish the Oklahoma native as Nashville royalty, along with an unflappable sense of poise and an innate business savvy. In a 2016 interview with Rolling Stone, she credited her longevity to both good songs choices and adapting to the times. “I love to record, the process of finding songs, going into the studio with the producers and musicians. I just really love the whole process of making music,” she said. “And social media is key, staying out there with the public and giving them what they want.” J.G. 

Key Tracks: “Whoever’s in New England,” “Fancy”

UNSPECIFIED - JANUARY 01: (AUSTRALIA OUT) Photo of Ralph STANLEY and Carter STANLEY and STANLEY BROTHERS (Photo by GAB Archive/Redferns)

Ralph Stanley and the Stanley Brothers

GAB Archive/Redferns

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Stanley Brothers

Both as a member of the Stanley Brothers with guitar-playing sibling Carter and as a solo artist, Ralph Stanley helped integrate bluegrass and Appalachian music into the country genre. With Carter, he recorded the definitive version of the traditional “Man of Constant Sorrow” in 1951, and backed by the band the Clinch Mountain Boys, the brothers became regulars on the region’s bluegrass circuit. Carter’s death in 1966 ended the duo, and the younger Stanley eventually carried on under his own name with a reconstituted Clinch Mountain Boys – at one point counting Ricky Skaggs and Keith Whitley among its members. Stanley experienced a major career renaissance in 2000, thanks to his inclusion on the soundtrack to the Coen Brothers’ O Brother, Where Art Thou. His rendition of the haunting “O Death” won him a Grammy for Best Male Country Vocal in 2002, a song he continued to perform a cappella onstage until his death in 2016 at 89. J.H.

Key Tracks: “Man of Constant Sorrow,” “O Death”

(Original Caption) 8/1957: Portrait of rock-and-roll recording artist Jerry Lee Lewis. He is shown full-length, playing piano.

Jerry Lee Lewis

Bettmann/Getty

34

Jerry Lee Lewis

Before threatening to shove biographer Nick Tosches’ tape recorder a place it was unlikely to fit, the Killer once summed music history thusly: “Y’know, son, there’s only been four of us: Al Jolson, Jimmie Rodgers, Hank Williams and Jerry Lee Lewis. That’s your only goddam four stylists that ever lived.” In 1968, when rock & roll was long done with him and nothing he recorded seemed to work, a 32-year-old Lewis proved the point by reshaping country songs of despair with his swagger and pumping piano: “Another Place, Another Time,” “What Made Milwaukee Famous (Has Made a Loser Out of Me)” and even a cover of Ernest Tubb’s 1941 classic “Walking the Floor Over You” were about empty rooms and lonely times, but Lewis made them romps. On “She Even Woke Me Up to Say Goodbye,” he could stand inside and outside heartbreak at the same time, and brought a reprobate’s knowledge to “Middle Aged Crazy” via the lines “He’s got a young thing beside him / That just melts in his hands.” From 1968 to 1977, Lewis sent 10 singles to the Top 10 on the Billboard country chart, four of them to Number One, by walking tall and leaving the lamentation to others. J.L. 

Key Tracks: “What Made Milwaukee Famous,” “Walking the Floor Over You”

Miranda Lambert performs at the nightly concert at The Coliseum on Sunday, June 11, in Nashville during the 2005 CMA Music Festival. (Photo by Ed Rode/WireImage)

Miranda Lambert

Ed Rode/WireImage

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Miranda Lambert

Miranda Lambert is such the complete artist today, miles above most of her peers, that it’s hard to believe she ever competed on a TV singing contest, the 2003 edition of Nashville Star. She didn’t win, but she nonetheless established herself as a creative force by co-writing almost all of her own songs. A Texas native who grew up with a love for tough-talking stars like Merle Haggard and Loretta Lynn, Lambert is a prime example of female empowerment in today’s country, with anthemic hits like “Gunpowder & Lead” and “Mama’s Broken Heart.” But she refuses to be pigeonholed, also scoring with sensitive singles like “The House That Built Me” and “Over You.” With six major label albums to her credit, she is the most awarded ACM Female Vocalist of the Year in history (eight times), a two-time Grammy winner and has so far collected 13 CMA awards, while also creating a successful side project with Ashley Monroe and Angaleena Presley, the Pistol Annies. Her latest album, the ambitious double record The Weight of These Wings, emphasizes the songwriting that first put her on the map, particularly the crushing “Tin Man,” which lays bare her own broken heart. C.P.

Key Tracks: “Gunpowder & Lead,” “The House That Built Me” 

MATLOCK -- "The Big Payoff" Episode 16 -- Pictured: Randy Travis as Billy Wheeler (Photo by Frank Carroll/NBC/NBCU Photo Bank via Getty Images)

Randy Travis

Frank Carroll/NBC/NBCU Photo Bank via Getty

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Randy Travis

Randy Travis and his oak-aged baritone returned country music to its down-home roots in the Eighties. Starting with 1986’s “On the Other Hand,” Travis’ run of hits mixed neo-traditionalist ballads with heavenly gospel songs that could make even the most hardened soul believe he had heard the voice of God. “Forever and Ever, Amen,” “I Told You So” and “Deeper Than the Holler” are essential to country music, all of them delivered by a voice that influenced artists from the Avett Brothers to Carrie Underwood. Tragically, Travis’ singing was curtailed by a stroke in 2013, but he regained his talent enough to perform “Amazing Grace” at his own Hall of Fame induction ceremony in 2016, a feat that cemented Travis as not just a country icon but an inspiration. J.G.

Key Tracks: “Diggin’ Up Bones,” “Forever and Ever, Amen”

Charley Pride performs on a TV show, London, February 1975. (Photo by Michael Putland/Getty Images)

Charley Pride

Michael Putland/Getty

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Charley Pride

Country music’s first black superstar started as a half-time entertainer while playing semi-pro baseball in Montana, an American pursuit he also helped integrate. A pure country stylist in the vein of Roy Acuff, who he grew up listening to, Pride’s creased baritone drove 19 consecutive Number Ones through the Seventies (“Kiss an Angel Good Morning,” “Amazing Love”). He won the CMA Entertainer of the Year Award in 1971, matter-of-factly breaking one more color barrier. W.H.

Key Tracks: “Kiss an Angel Good Morning,” “Is Anybody Goin’ to San Antone”

NASHVILLE - CIRCA 1965: Lester Flatt (left) and Earl Scruggs (right) pose for a portrait circa 1965 in Nashville, Tennessee. (Photo by Michael Ochs Archives/Getty Images)

Flatt & Scruggs

Michael Ochs Archives/Getty

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Flatt & Scruggs

When Lester Flatt and Earl Scruggs first formed their legendary bluegrass group the Foggy Mountain Boys in 1948, the duo had already left an unforgettable mark on the history of the then-burgeoning genre as members of Bill Monroe’ pioneering band. But with their own group, the duo would transform bluegrass and solidify its signature sound, thanks to Scruggs’ famous three-finger banjo-picking style and Flatt’s fast-paced rhythm guitar and high-lonesome vocals. The duo performed together for more than two decades, during which time they became the country’s foremost representatives of bluegrass, before splitting up, largely due to musical differences, in 1969. Before the breakup, however, the group released four Top Ten country albums and left behind an indelible legacy of bluegrass standards that still define the genre a half-century later. “If it wasn’t for Earl Scruggs,” John Hartford once said, weighing in on the debate over who originated bluegrass-style banjo, “you wouldn’t be worried about who invented it.” Jonathan Bernstein

Key Tracks: “Foggy Mountain Breakdown,” “The Ballad of Jed Clampett”

Kris Kristofferson Playing Guitar (Photo by �� John Springer Collection/CORBIS/Corbis via Getty Images)

Kris Kristofferson

John Springer Collection/CORBIS/Corbis via Getty

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Kris Kristofferson

Educated at Oxford in England, trained as an Army pilot, and blessed with rugged good looks but an equally craggy voice, Kristofferson seemed like the last person you’d expect to launch a music career in the Sixties. Yet that unconventional background – especially his interest in creative writing – inspired Kristofferson to take country lyricism to a new, more literary level as a writer and performer. Densely written and world weary, songs like “Sunday Morning Coming Down” (popularized by Johnny Cash) and “For the Good Times” inserted an introspective depth into country, and “Help Me Make It Through the Night” (a huge hit for Sammi Smith) injected a sexy intimacy into the music. Toss in now-standards like “Me and Bobby McGee,” “From the Bottle to the Bottom” and “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again),” and Kristofferson earned his stature as country’s poet laureate. D.B.

Key Tracks: “Sunday Morning Coming Down,” “Me and Bobby McGee” 

Alan Jackson during Paul Natkin Archive, United States. (Photo by Paul Natkin/WireImage)

Alan Jackson

Paul Natkin/WireImage

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Alan Jackson

Few country artists have had bigger careers than Alan Jackson, though he’d never be the first one to tell you. The quiet man of country stars, Jackson has been a steady hand throughout his nearly 30 years in the spotlight, during which he’s racked up more than 30 Number One singles and sold over 80 million records. Appropriately, it was Jackson’s wife who helped him catch his big break, handing off a demo on a chance encounter with Glen Campbell, who signed the Newnan, Georgia, native to his publishing company. Jackson’s glossy traditionalism shines on hits like “Midnight in Montgomery,” “Don’t Rock the Jukebox” and “Where Were You (When the World Stopped Turning)” – country music’s definitive memorial to 9/11 ­– proving that Jackson needn’t ever say a word; the music speaks for itself. J.G.

Key Tracks: “Chattahoochee,” “Midnight in Montgomery”

Bluegrass music legend Bill Monroe sings and plays a mandolin.

Bill Monroe

Bettmann/Getty

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Bill Monroe

The Kentucky farm son who became the Father of Bluegrass – his bronze likeness now stands outside Nashville’s Ryman Auditorium – worked as a buck dancer during the Depression before turning musician, and he brought that physical joy to the sound of the Blue Grass Boys. With the hot picking of banjo virtuoso Earl Scruggs and guitarist Lester Flatt alongside Monroe’s mandolin, the bandleader forged a new sound full of showboat soloing and mountain soul. It took the Grand Ole Opry by storm in the 1940s, inspiring countless musicians along the way. Country music would never be the same. W.H.

Key Tracks: “Blue Moon of Kentucky,” “Rocky Road Blues” 

UNSPECIFIED - CIRCA 1970: Photo of Tom T. Hall Photo by Michael Ochs Archives/Getty Images

Tom T. Hall

Michael Ochs Archives/Getty

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Tom T. Hall

Hall’s songwriting has been compared to Chekhov’s short stories and with good reason. “I couldn’t write the ‘Darling, you left alone and blue’ or ‘I’m drunk in this bar and crying’ [songs] – I just didn’t get it,” he once said. “And so I started writing these story songs.” Hall brought humor, warmth and some of the most vividly descriptive lyrics in the history of American music to songs like “Old Dogs, Children and Watermelon Wine,” written after a brief encounter with a janitor at a bar at the 1972 Democratic Convention. “Don’t Forget the Coffee Billie Joe” is about a seven-mile walk into town in the winter of ’49 with a shopping list from dad that’s like a catalog of rural struggle and community (“mama needs her medicine / She’s got that real bad cough / We’ll get our check on Monday / Tell ol’ Sam we’ll pay him off’). Hall’s biggest hit was “Harper Valley PTA,” a hilarious study in small-minded, small-town hypocrisy that was a Number One pop and country hit for Jeannie C. Reilly in 1968. An English major and committed liberal, Hall infused his songs with a learned tenderness, like in “The Hitchhiker,” where he picks up a country boy in search of a job outside of Prestonsburg, Kentucky, buys him a diner hot dog (“with a lot of table ketchup“) and arrives at the bottomless life lesson “boy, you’ll never make it without help.” J.D. 

Key Tracks: “That’s How I Got to Memphis,” “Old Dogs, Children and Watermelon Wine”