100 Greatest Country Artists of All Time

Hitting his streak during the war-torn 1970s, John Denver kept things peppy and pleasant, walking the family-friendly line between country, soft folk and easy listening. The man had vices, but he largely kept them out of his songs, choosing instead to glorify the great outdoors in hits like “Take Me Home, Country Roads.” Uncool? Perhaps. When Denver was named Entertainer of the Year by the CMA in 1975, presenter Charlie Rich responded by setting fire to the envelope containing Denver’s name, which many viewers interpreted as a repudiation of country’s pop-friendly crossover. But Denver, with his goofy grin and awww-shucks demeanor, was always content to ride his own Rocky Mountain High, leaving protest music, country classicism and the rock & roll lifestyle to his contemporaries. “I don’t mind if they call me the Mickey Mouse of rock,” he told Rolling Stone‘s Chet Flippo in 1975. His fans didn’t mind, either, and by the decade’s end, Denver had racked up nine Number One hits on multiple charts. His influence on country music remains apparent – decades after its release, “Country Roads” was the backbone of 2016’s “Forever Country,” a mash-up celebrating the CMA Awards’ 50th anniversary. Andrew Leahey

Key Tracks: “Take Me Home, Country Roads,” “Thank God I’m a Country Boy”

American Idol‘s fourth-season winner was a shoo-in from the start, with noted grump Simon Cowell proclaiming her the guaranteed victor early on – but even he probably never realized how far she’d take her talent. Her powerful voice and girl-next-door vibes added both weight and accessibility to early singles like the let-go-let-God anthem “Jesus, Take the Wheel,” but it was the revelation of her bad side on 2005’s revenge treatise “Before He Cheats” that endeared her to pop fans. Underwood is a legit Nashville crossover, but one with the promise and poise to evolve the genre and maintain its roots – she’s been a Grand Ole Opry member since 2008. It’s no stretch to imagine her being the first reality-show winner ever inducted into country’s Hall of Fame. Maura Johnston

Key Tracks: “Jesus, Take the Wheel,” “Something in the Water”

Australia’s biggest country-music export since Slim Dusty, Keith Urban became one of the genre’s most celebrated guitar heroes during the early 21st century, championing a crossover-friendly playing style rooted not in the chicken-pickin’ flash of many country instrumentalists, but the tone and nuance of rock & rollers like Mark Knopfler. During the two decades since, his songs have tread a similar line, rooting themselves in the epic gestures of arena rock, the digital elements of pop and the storytelling of contemporary country. Several months shy of his 50th birthday, Urban remains a favorite among Baby Boomers and Millennials alike, thanks to a five-season run as an American Idol judge — a gig that plastered his face across the TV screens of 10 million weekly viewers — and a string of hit singles that never shy away from current trends. A.L.

Key Tracks: “Somebody Like You,” “Stupid Boy,” “You’ll Think of Me”

Brad Paisley stands out as the poster boy for the genre’s time-honored traditions. One of the biggest stars of the 21st century, the West Virginian has had 19 singles top the country charts, many of which, like “I’m Gonna Miss Her (The Fishin’ Song)” and “She’s Everything,” instantly resonated with fans. His 2009 album American Saturday Night established Paisley as a forward-thinking country artist, and his stature was only validated by his record sales. His dexterity on guitar makes him country’s Eddie Van Halen, and he’s also one of the most incisive songwriters of his generation. As he hits middle-age, his star-studded Love and War (his ninth consecutive LP to go Number One) has reinforced another old-school idea in 2017: growing old gracefully. Jeff Gage

Key Tracks: “I’m Gonna Miss Her (The Fishin’ Song),” “Welcome to the Future,” “When I Get Where I’m Going”

An Oklahoma native and former oil-rig worker, Toby Keith has tapped into the blue-collar lifestyle with humor and sincerity since his debut single, “Should’ve Been a Cowboy,” hit Number One in 1993. With a booming voice and roughneck persona, he’s gone on to become one of the most successful, recognizable and controversial artists in the modern country era. Keith has released 17 studio albums, sold more than 40 million copies and tallied 20 Number Ones hits to date – including “Courtesy of the Red, White, and Blue (The Angry American),” which was written in response to the September 11, 2001, terrorist attacks. Striking a defiant tone, the song and its “boot up your ass” hook became synonymous with Keith, who released a string of pro-America songs in the years following: “American Soldier,” “American Ride” and “Made in America,” all of which topped the charts. Despite all the flag-waving, Keith isn’t a one-note artist. His wonderfully self-deprecating “As Good As I Once Was” and the heartbreaking “Cryin’ for Me (Wayman’s Song)” mine country tradition and highlight one of the richest baritones in the business. Chris Parton

Key Tracks: “You Shouldn’t Kiss Me Like This,” “As Good As I Once Was,” “Honkytonk U”

Kix Brooks and Ronnie Dunn separately kicked around Nashville during the Eighties, scoring minor hits while working as writers for hire. Introduced and paired up in the early Nineties, they were seemingly the perfect match: Dunn the reserved and serious type with the soaring voice, Brooks the gregarious showman. Together, they blended classic country ideas with honky-tonk’s raucousness, pop’s sticky-sweet hooks and just enough dancefloor-ready sass to get listeners boot-scootin’ along. Their incredible singles run included a slew of CMA awards and 23 country Number Ones, among them the drinking weeper “Neon Moon,” the nostalgia-tinged “Red Dirt Road” and the ubiquitous line-dancing anthem “Boot Scootin’ Boogie.” The duo split in 2010 but reunited in 2015 for an ongoing Vegas showroom run with Reba McEntire. M.J.

Key Tracks: “Boot Scootin’ Boogie,” “Believe,” “Red Dirt Road”

Although rooted in bluegrass and traditional country, Alison Krauss has stamped her watermark across the full range of American roots music, winning a record-tying number of Grammy Awards with her solo albums, her work alongside the progressive string band Union Station, several contributions to the multi-platinum O Brother, Where Art Thou? soundtrack and a stunning duets album, Raising Sand, with rock god Robert Plant. Glueing those projects together is her impressive fiddle work and one of the modern age’s most unique voices: a cool, cooing soprano that’s equal parts silk and swagger, capable of tackling high-lonesome folk one minute and sacred Southern gospel the next. A.L.

Key Tracks: “Please Read the Letter,” “Down to the River to Pray”

Though not a native Texan, Jerry Jeff Walker was one of the artists who helped put the Lone Star State – and, in particular, the city of Austin – on the country music map in the 1970s. Originally from New York state, Walker’s best-known song was 1968’s “Mr. Bojangles” (a Top 10 pop hit in the hands of Nitty Gritty Dirt Band), but he was immortalized five years later with the highly influential live album Viva Terlingua! Recorded in Luckenbach before Waylon and Willie and the boys made the town famous, Terlingua‘s Tejano-infused “gonzo country” (his crack backing band including Gary P. Nunn and Bob Livingston were dubbed the Lost Gonzo Band) was more Texas than the outlaws themselves and became a cornerstone of Red Dirt country music. J.G.

Key Tracks: “Gettin’ By,” “Sangria Wine,” “Mr. Bojangles”

The life of the cowboy is one of country music’s central narratives, to the point of being cliché, but it’s the existence that Chris LeDoux actually lived. A bareback national rodeo champion, the Wyoming native’s ranch songs were the real deal, and he played the part of the maverick to a T, even refusing to sign a record contract because he preferred to play by his own rules. Until, that is, Garth Brooks’ shout-out on ‘Much Too Young (To Feel This Damn Old)” made it too tempting to not cash in. Their subsequent duet, “Whatcha Gonna Do With a Cowboy,” helped give LeDoux his due and his mystique has only grown since his untimely death at 56 from cancer in 2005. J.G.

Key Tracks: “This Cowboy’s Hat,” “Whatcha Gonna Do With a Cowboy”

“Shouldn’t I have all this?” Lucinda Williams asks on her signature song “Passionate Kisses,” and few lines could sum up the Louisiana native’s distinct vision better. A consummate perfectionist, Williams has made a career of holding out to do things her way, often spending years to get her albums just right; her masterpiece, 1998’s Car Wheels on a Gravel Road, was six whole years in the making. That meant years of cult fandom but little in the way of the wider spread notoriety “the female Bob Dylan” deserved. But that’s just as well – Williams’ gritty voice is one of the most distinctive there is, and it’s all hers. “I’m kind of an anomaly. I got discovered late. And here I am, at my age,” she said earlier this year. “I have to do this.” J.G.

Key Tracks: “Passionate Kisses,” “Drunken Angel,” “Right in Time”

Brenda Gail Webb, unlike her Kentucky-born older sister Loretta Lynn, was raised in Indiana, cultivating a polished persona and singing style tailor-made for country-pop crossover. “I went middle-of-the-road because Loretta said, ‘Don’t sing my songs and don’t sing anything I would sing, because you’ll be compared,'” Gayle told Rolling Stone in 2014. “She was right. I wouldn’t have made it if I had just done that. But I love those songs.” Her earliest singles only dented the charts, but in the late Seventies and early Eighties, Gayle hit her stride. The Grammy-winning “Don’t It Make My Brown Eyes Blue” was a country chart-topper and Number Two pop monster, followed by two more Top 20 pop singles and a total of 18 country Number Ones. In addition to her country pedigree she’s been a consistently sophisticated interpreter of pop standards and was made a member of the Grand Ole Opry in January 2017. Stephen L. Betts

Key Tracks: “Don’t It Make My Brown Eyes Blue,” “When I Dream,” “Ready for the Times to Get Better”

Topping the charts for the first time in 1994, Tim McGraw has stood at the helm of country-pop’s ever-changing mainstream for nearly a quarter century, outlasting virtually everyone — from Garth Brooks to the Dixie Chicks — who once battled him for radio airtime. It’s no surprise that Millennial queen Taylor Swift, who was barely one year old when McGraw signed his first record contract, chose to name her debut single after the singer. Now in his fifties, he’s still the walking embodiment of his own genre: a rugged, muscled, cowboy-hatted man from the Deep South, married to a country queen (Faith Hill, whose voice can be heard on a handful of his biggest hits) and fathered by a sports hero. Trends come and go, but McGraw remains. A.L.

Key Tracks: “Something Like That,” “Live Like You Were Dying”

One of the most dynamic vocal groups in the history of country, the mother-daughter duo of Naomi and Wynonna Judd were peerless hitmakers in the Eighties. In a mainstream run that only lasted eight years at its height, they scored a staggering 14 Number One singles, but the success of anthems like “Girls Night Out” and “Why Not Me” – which drew heavily on the Kentucky natives’ roots in bluegrass – was hard-earned, as they’d spent years passing around cheaply-recorded cassettes before getting signed. But spurred by Wynonna’s songwriting, the Judds became a major force, and their music possessed a keen sense of female empathy. Naomi’s hepatitits C diagnosis cut short their often-tumultuous run in 1991, opening the door for Wynonna, who had increasingly asserted herself alongside her mother, to parlay her prodigious skills into her own successful solo career. J.G.

Key Tracks: “Girls Night Out,” “Why Not Me,” “Turn It Loose”

Possessing a deep, muddy baritone of a voice and a songwriting style rooted in tradition that also appealed to older fans, Alabama native Jamey Johnson only hit country radio’s Top 10 once, with 2008’s nostalgic “In Color.” It was enough, though, to demonstrate that an audience still existed for artists with an ear for classic – even outlaw – sounds, helping to pave the way for independently-minded success stories like Sturgill Simpson and Aaron Watson to come. Johnson also proved that the album format wasn’t dead, reaching Platinum status with 2008’s That Lonesome Song and earning a Gold certification for his 2010 Number One double LP, The Guitar Song, without the help of another significant radio hit. As a writer, he possesses a wide range of ability, co-writing both George Strait’s “Give It Away” and Trace Adkins’ “Honky Tonk Badonkadonk.” While he’s talked here and there about new music to come, the reclusive Johnson has remained largely silent since 2015. C.P.

Key Tracks: “In Color,” “Playing the Part”

Nicknamed “Whisperin’ Bill” for his soft-spoken delivery, South Carolina-born, Georgia-raised Bill Anderson is a dual threat performer and songwriter with hits spanning numerous decades. A journalism major in college, Anderson applied his eye for detail to musical composition, landing hits with Ray Price (“City Lights”) and Connie Smith (“Once a Day”), among others. He had seven chart-topping hits under his own name, including “Mama Sang a Song” in 1962 and “Still” in 1963, continuing to chart through the end of the Seventies. After a detour into television, Anderson got his second wind as a songwriter in the 1990s and 2000s, co-writing Brad Paisley and Alison Krauss’ haunting “Whiskey Lullabye” and the George Strait instant classic “Give It Away,” with Jamey Johnson. He was inducted into the Country Music Hall of Fame in 2001, living proof that Nashville and country music truly thrives on the work of great songwriters. Jon Freeman

Key Tracks: “Mama Sang a Song,” “Still”

By the time he released his 2011 breakthrough Chief, Eric Church was well on his way to perfecting his mix of Kristofferson songcraft and Kiss showmanship, a blend he supersized on 2014’s The Outsiders. And then, he promptly blew it all up, recasting himself as country’s Springsteen on the singer-songwriter masterpiece Mr. Misunderstood. Such evolution is Church’s calling card, which makes it exciting to speculate on what his albums five or even 10 years from now might sound like. A tireless live act, the Chief’s recent Holdin’ My Own Tour boasted three-hour-plus shows, every minute commanded by an artist who is always thinking two steps ahead. “I want everybody in that place to feel like they experienced something, that they felt something,” he said of his one-of-a-kind live shows in a 2014 Rolling Stone Country interview. “They’re going to tell people, ‘That show was spiritual to me. I felt it.'” Joseph Hudak

Key Tracks: “Sinners Like Me,” “Smoke a Little Smoke,” “Mr. Misunderstood”

One of the best songwriters of his generation, Steve Earle is an iconoclast to the core – and, at various times throughout his life, his own worst enemy. His hero and later best friend was Townes Van Zandt, and Van Zandt’s tortured run to an early grave was in many ways the template for the demons that often crept into Earle’s life. In 1986, he scored his breakthrough with Guitar Town, a roots record that was as much rock & roll as it was country. Earle soon spiraled into substance abuse, but he did one thing his hero couldn’t do: bouncing back with some of his finest work. He’d also branch into playwriting and novels, as his son, Justin Townes Earle, rose up as a gifted songwriter in his own right. Not that he’s one to fuss over himself: “It’s really just some songs that gotten written accidentally,” he told Rolling Stone last year. J.G.

Key Tracks: “Copperhead Road,” “Goodbye’s All We Got Left,” “Fort Worth Blues”

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” 

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”

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?”

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”

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)” 

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”

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” 

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”

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”

“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”

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”

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”

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” 

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” 

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”

“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” 

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)”

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”

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”

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”

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”

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”

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”

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” 

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”

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”

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” 

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”

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”

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”

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”

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” 

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”