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The 200 Greatest Country Songs of All Time

From Hank to Shania, from George Strait to Beyoncé

Greatest country songs of all time

PHOTO ILLUSTRATION BY GRIFFIN LOTZ. PHOTOGRAPHS IN ILLUSTRATION BY ETHAN MILLER/GETTY IMAGES; MICHAEL OCHS ARCHIVES/GETTY IMAGES, 2; AARON RAPOPORT/CORBIS/GETTY IMAGES; GAB ARCHIVE/REDFERNS/GETTY IMAGES; ADOBE STOCK

WHAT MAKES A great country song? It tells a story. It draws a line. It has a twang you can feel down to the soles of your feet. Some get mad, some get weepy, some just get you down the road. And these are the songs that map out the story of country music — from Hank Williams howling at the moon to Ray Charles giving “hillbilly” music an R&B makeover to Shania Twain taking her karaoke-cowgirl feminism worldwide, and much more.

In 2014, Rolling Stone launched Rolling Stone Country and inaugurated the new site with a list of the 100 Greatest Country Songs. Now, to celebrate the 10th anniversary of RS Country, we’re expanding the list to 200 songs. The new list gave us more room to go deeper into the music’s rich history, including some aspects that didn’t get enough attention the first time around. We’re publishing our updated list at a time when a classic Tracy Chapman folk song can become a country Number One, and Beyoncé’s Cowboy Carter is shining a light on the legacies of Black country artists like Linda Martell. Nearly a century after artists like the Carter Family, Jimmie Rodgers, and DeFord Bailey helped get the story started, the tradition keeps growing.

CONTRIBUTORS: Joseph Hudak, Jon Freeman, Christopher Weingarten, David Cantwell, Brittney McKenna, Angie Martoccio, Michaelangelo Matos, Joe Gross, Jeff Gage, Rob Sheffield, Nick Murray, Will Hermes, Keith Harris, Jon Dolan, Maya Georgi, Richard Gehr, Reed Fischer, Jonathan Bernstein, Beville Dunkerley, Cady Drell, Marissa R. Moss, David Menconi, Linda Ryan, Andrew Leahey, Mike Powell, Charles Aaron, Rob Harvilla, Amanda Petrusich

From Rolling Stone US

125

Guy Clark, ‘L.A. Freeway’

Easily one of the most well-respected songwriters in the long history of Texas music, Guy Clark headed to Nashville in 1971 and scored right out of the gate with this ode to getting out of Los Angeles, all but creating the outlaw country-folk fusion we think of as “Americana” in the process. The song was first recorded by Jerry Jeff Walker in 1972 for his self-titled album. Where Walker makes the song’s famous chorus (“If I can just get off of this L.A. freeway/Without gettin’ killed or caught”) sound like a toss-up, Clark’s much more melancholic take on his landmark 1975 debut, Old No. 1, suggests that the end is extremely nigh. —J. Gross   

124

George Strait, ‘The Chair’

By 1985, George Strait was the embodiment of a powerful and popular strain of country music — rootsy in his arrangements and straight-forward in his delivery, few people could better serve the song itself. Strait sounds downright suave on this slow-dance hit, the first single from his fifth studio album, Something Special. No chorus and just verses means it’s nothing but story: A woman in a bar is accidentally warming his seat, a drink is bought, a dance ensues, and he gets to drive her home, closing with a credible twist. Strait’s such a pro that he can perfectly sell a goofy line like, “Thank you, could I drink you a buy?/Oh, listen to me, what I mean is, can I buy you a drink?” —J. Gross

123

Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash, ‘Highwayman’

This Jimmy Webb story-song, tracing a spirit’s reincarnations via four distinct characters, was recorded by both Webb and Glen Campbell in the ‘70s. But outlaw supergroup the Highwaymen made it canon, taking both their band name and, to an extent, their identity from it. With flickers of the Band and the Temptations in its tag-team vocals, it was a country Number One, scored a Grammy, and reheated flagging careers all around. Decades later, it also helped spur Amanda Shires to form the Highwomen with Brandi Carlile, Maren Morris, and Natalie Hemby, and to revise the song with Webb’s help (and a Yola cameo), channeling an outlaw spirit that refuses to die. —W.H.

122

Brothers Osborne, ‘Younger Me’

When TJ Osborne came out as gay in early 2021, the Brothers Osborne vocalist became — and remains — one of just a few out queer musicians in popular country music. Two months later, the duo released “Younger Me,” an emotional accounting of TJ’s journey to self-acceptance. While the song is deeply personal, Osborne hoped it would offer comfort and inspiration for queer fans finding themselves, as well as make the genre more welcoming to a broader swatch of people. The move paid off critically, too, as the song’s 2022 trophy for Best Country Duo/Group Performance earned the band its first Grammy win after seven prior nominations. —B.M.

121

Ray Wylie Hubbard, ‘Redneck Mother’

This second-tier Texas outlaw still writes, performs, and records, but Ray Wylie Hubbard dreamed up his only classic tune (recorded most famously by Jerry Jeff Walker, though Nineties alt-rockers Cracker do a killer version), early in his career, while kicking around in New Mexico. “Redneck Mother” flips a popular slogan among revolutionaries (as in, “Up against the wall …”) and flips the bird to country’s mother-worship. Never mind what Merle said — mama didn’t try hard enough, Hubbard suggests. If she had, maybe there wouldn’t be so many good-for-nothing drunks out there “kickin’ hippies’ asses and raisin’ hell.” —K.H.

120

The Charlie Daniels Band, ‘The Devil Went Down to Georgia’

Charlie Daniels was the self-proclaimed “Long Haired Country Boy” who worked both sides of the country/rock border. After starting out in bluegrass, he became a Music Row session cat whose first big break was playing on Bob Dylan’s 1969 Nashville Skyline. He also backed up Ringo Starr and Leonard Cohen. But the bearded Southern-rock grizzly topped the country charts with “The Devil Went Down to Georgia,” doing for air fiddle what “Free Bird” did for air guitar. It’s the rowdy tale of a backwoods boy named Johnny who gets challenged to a fiddle duel by the Prince of Darkness. Spoiler: After Johnny wins, he trash-talks the Devil, “I done told you once, you son of a bitch, I’m the best that’s ever been!” —R.S.

119

Moe Bandy, ‘I Just Started Hatin’ Cheatin’ Songs Today’

Moe Bandy was the quintessential Seventies honky-tonk everyman with his theme song, “Hank Williams, You Wrote My Life.” He spent his teens riding bulls on the rodeo circuit — he’s in the Texas Rodeo Hall of Fame. But he moved on to music, pawning all his furniture to pay for a $900 recording session, resulting in his barstool confession “I Just Started Hatin’ Cheatin’ Songs Today.” “I really think my songs are about life,” Bandy said. “There’s cheating, drinking, and divorcing going on everywhere, and that’s what hardcore country music is all about.” He kept at the cheatin’ theme with hits like “I Cheated Me Right Out of You,” “Soft Lights and Hard Country Music,” and a Lefty Frizzell-penned nod to his former career, “Bandy the Rodeo Clown.” —R.S.

118

Faith Hill, ‘This Kiss’

It’s impossible to explain “This Kiss” without bringing up that scene in Practical Magic, where Sandra Bullock’s aunts cast a love spell on her, and she abruptly stops tending to her garden and rushes into the arms of a hot guy at a farmer’s market. It sums up exactly what it was like to hear “This Kiss” in 1998, from the churning guitar riff to lines like “It’s centrifugal motion/It’s perpetual bliss.” “This Kiss” was Faith Hill’s breakthrough hit, crossing over into the mainstream and landing at Number Seven on the Billboard Hot 100. She’d go on to release many other upbeat gems (“The Way You Love Me,” “Mississippi Girl”) but nothing hits quite like “This Kiss,” where she took a simple act of love and made it into a country-pop anthem. —A.M.

117

Harry Choates, ‘Jole Blon’

One of Bruce Springsteen’s lesser-known influences is the late, hard-drinkin’ Texas fiddle player Harry Choates. After playing for spare change as a teenager in the Thirties, Choates started making records by his early Twenties, and his aching 1946 reworking of the so-called “Cajun national anthem” hit Number Four on the Billboard country chart. “Jole Blon,” a traditional cajun waltz with nearly indiscernible lyrics about a pretty blonde, rode commercial success via several reinterpretations and continued in country lore throughout the decade. It passed through the hands of Roy Acuff, Warren Zevon, and Springsteen (who recorded an early Eighties version with Gary U.S. Bonds), among many others. Fame and fortune never made it back to Choates, however. According to legend, he sold “Jole Blon” for $100 and a bottle of whiskey and died at the age of 28. —R.F.

116

Statler Brothers, ‘Flowers on the Wall’

Four high school buddies from Virginia who met singing in church, the Statlers were Johnny Cash’s backup singers for years, and they got signed to Columbia Records in the mid-Sixties at Cash’s behest. Written by tenor singer Lee DeWitt, their breakout 1966 hit, “Flowers on the Wall,” touched a crossover nerve with its absurdist lyrics about a post-breakup meltdown, especially the classic line “Smokin’ cigarettes and watchin’ Captain Kangaroo/Now don’t tell me, I’ve nothin’ to do.” Novelist Kurt Vonnegut loved the song so much he called the band “American poets,” and Quentin Tarantino deployed it very effectively in Pulp Fiction. —J.D.

115

Ronnie Milsap, ‘Smoky Mountain Rain’

This story of returning home from the city was told through thunderous piano playing (inspired by Ronnie Milsap’s session work on Elvis Presley’s “Kentucky Rain”) and producer Tom Collins’ spiraling strings. Of course, “Smoky Mountain Rain” wouldn’t be on this list if the words weren’t equally chilling: Note, for instance, that before the protagonist heads back to North Carolina, he has not a change of plans but a “change of dreams.” Written by Kye Fleming and Dennis Morgan, who were instructed by Collins to come up with a song about his actual home state, “Smoky Mountain Rain” was Milsap’s fourth Number One of 1980 alone. —N.M.

114

K.T. Oslin, ’80’s Ladies’

The late K.T. Oslin beat the odds in more ways than one with this hit. For one thing, Nashville’s typical marketing outlook was upended when a song by a woman in her mid-forties shot to Number One on Billboard’s country chart, as did the album named after it. For another, it was a woman-power song at a time when feminism was not a widespread song topic. Oslin’s giant, irresistible chorus celebrated both: “We were the girls of the ’50s/Stone rock and rollers in the ’60s.” The booming production is very ’80s, just like the title promises. —M.M.

113

Tracy Chapman, ‘Fast Car’

Thirty-five years after Tracy Chapman first released her ballad about speeding away from a bleak existence, she became the first Black woman to have a Number One country song as the sole writer, and then became the first Black songwriter to win the CMA Award for Song of the Year. Luke Combs, of course, helped revive “Fast Car,” recording an exquisite (and faithful) version for his album Gettin’ Old. But the country star knew the credit all goes to Chapman: When Combs won Single of the Year at the CMAs, he started by thanking her by name for “writing one of the best songs of all time.” —J.H.

112

Johnny Cash and June Carter, ‘Jackson’

Johnny Cash and June Carter weren’t yet a couple when they cut “Jackson” in the winter of 1967, but more than any of their storied collaborations, it crackles with an chemistry. Written after co-author Billy Edd Wheeler read the script for Who’s Afraid of Virginia Woolf?, “Jackson” would have further success with Nancy Sinatra and Lee Hazelwood’s drowsy rendition, but Cash and Carter made it wholly their own, propelled by a whip-cracking guitar line and smoldering banter. Cash’s unquenchable infatuation with Carter no doubt helped; in the worst throes of his drug addiction, he’d asked repeatedly for her hand in marriage, and she always refused. —J. Gage

111

Garth Brooks, ‘The Dance’

The second Number One single off Garth Brooks’ debut LP, “The Dance” is a better-to-have-loved-and-lost slow jam that co-writer Tony Arata had been playing to open-mic nights since he had moved to Nashville a few years earlier. “The only folks listening, however, were other songwriters,” remembers Arata. When Brooks first heard him play “The Dance,” he swore he would record the song if he ever got signed. —L.R.

110

Tim McGraw, ‘Something Like That’

It’s often referred to as “The BBQ Stain Song,” but this is much more than a catchy tune about condiment spillage. Released in 1999, “Something Like That” not only crossed over, but spent the next decade racking up half a million radio spins, becoming one of Tim McGraw’s many songs to top the country chart. That’s because this song is nothing but a good time, a track full of jubilant energy that’s jam-packed with the details of a summer romance — a tan line, a miniskirt, and plenty of red lipstick. Many country songs try too hard to capture that rush of youthful love. All McGraw had to do to get that feeling just right was go to the county fair. —A.M.

109

Crystal Gayle, ‘Don’t It Make My Brown Eyes Blue’

Loretta Lynn’s little sister is a coal miner’s daughter too, but one who grew up in small-town Indiana, not a Kentucky holler, and who grew up listening to the Nashville sound. Her signature country hit, which climbed to Number Two on the pop chart, reflects those changed circumstances. “Don’t It Make My Brown Eyes Blue” tells a broken-hearted love story (“say anything but don’t say goodbye”) that’s older than the hills, and its sound likewise is both familiar and one of a kind. It’s the Nashville sound, but it’s also borderline yacht rock coming smack in the middle of the outlaw era, as well as an easy-listening gem but with Pig Robbins contributing piano roiled by hard loss. Let’s call it Crystalpolitan. —D.C.

108

Gram Parsons, ‘$1000 Wedding’

Devotees have been puzzling over the meaning of this enigmatic masterpiece for 40 years, but it has yet to yield a definitive interpretation. Gram Parsons’ protagonist is a none-too-bright bridegroom at a low-rent (possibly shotgun) wedding, where he is stood up for reasons unknown. Maybe the bride died, maybe she ran off with someone else — it’s never specified. So he and his groomsmen go on a drunken bender so epic, “It’s lucky they survived.” Wedding seems to morphs into funeral, leading to the saddest closing line in all of country music: “It’s been a bad, bad day.” For all that the words leave unspoken, there’s no mistaking Parsons’ tone of stoic, bemused resignation. Duet partner Emmylou Harris blesses the proceedings with the perfect note of angelic sadness. —D.M.

107

Merle Haggard, ‘If We Make It Through December’

The biggest crossover hit of Merle Haggard’s career foils expectations straight down the line: It’s a Christmas song minus any holiday cheer. It’s a working-class anthem about getting “laid off” in the stagflation Seventies. It even finds the Hag, born and bred in gritty Bakersfield, California, embracing the Nashville sound. Pretty snowfall piano, chilly ooh-oohing backing singers, and a fiddler who sounds suspiciously like a violinist — they all combine to fuel Haggard’s American dream of a better life in a warmer climate. Right now, though, his little girl deserves a present or two he just can’t afford. Haggard’s voice shivers helplessly, and not because it’s cold. —D.C.

106

C.W. McCall, ‘Convoy’

This loving, jargon-filled novelty song took the insular world of trucker culture to the tops of both the country and pop charts in 1976. “Convoy,” an ode to CB radio, gave Iowa singer C.W. McCall the only Number One hit of his career, sold 2 million copies, started a CB radio fad, and even spawned a successful action movie of the same name. “The truckers were forming things called convoys, and they were talking to each other on CB radios,” explained McCall, who co-wrote the song with Chip Davis. “They had a wonderful jargon. Chip and I bought ourselves a CB radio and went out to hear them talk.” That’s a 10-4, good buddy. —J.B.

105

Merle Travis, ‘Sixteen Tons’

This classic labor song began when Capitol Records tasked singer-songwriter Merle Travis to hop on the folk boom of the mid-1940s. Travis rapidly cooked up the darkly humored original “Sixteen Tons,” inspired by his upbringing in the coal-mining hub of Muhlenberg County, Kentucky. Though its corresponding 1947 concept album Folk Songs of the Hills would not prove to be a chart success, songs like “Sixteen Tons” and “Dark as a Dungeon” would become standards, and Travis returned as a hero when the next folk boom peaked in the 1960s. According to Travis’ son, Tom Bresh, the songwriter would regularly quip, “[I] never did like that tune till Tennessee Ernie Ford sold about 5 million copies. Then, I got to where I loved it.” —C.W.

104

Kenny Rogers and Dolly Parton, ‘Islands in the Stream’

Written by the Bee Gees, the country crossover event of 1983 was originally a Motown-style R&B song intended for Diana Ross. It ultimately landed with Kenny Rogers, who spent four fruitless days in an L.A. session attempting the tune on his own. To salvage the song, the Bee Gees’ Barry Gibb suggested some assistance from Dolly Parton who, coincidentally, Rogers’ manager spotted nearby. The spontaneous collaboration yielded a creative relationship that lasted decades — and romantic rumors that seemed to have lasted just as long. “Dolly and I have been accused of having an affair for the last 30 years,” Rogers told CBS This Morning. “And we never did. What we’ve done is we’ve flirted with each other for 30 years. I do it in front of my wife because I know it’s harmless.” —C.W.  

103

Billy Joe Shaver, ‘Old Five and Dimers Like Me’

Of all the artists who got labeled outlaws during the Seventies, none came close to the real thing than Billy Joe Shaver, a former mill worker from Waco, Texas, who lost a couple of fingers on the job, survived an onstage heart attack, and shot a man in the face during a bar fight. But for all that reckless living, he had a knack for deep, introspective songwriting that changed the vernacular of the genre. On his signature tune, Shaver’s warbling, brittle voice has the perfect plainspoken quality for his tale of a two-bit hustler who couldn’t help but dream of bigger things. “I’ve spent a lifetime making up my mind to be/More than the measure of what I thought others could see,” he sings, and you know he lived that, too. —J. Gage

102

Juice Newton, ‘Queen of Hearts’

Originally a member of the short-lived band Silver Spur, Juice Newton had been releasing a steady output of solo pop and rock material for two years — to decent reviews but few sales. When she shifted to a more country sound for 1981’s Juice, she scored three Top 10 hits. The breakout track was “Queen of Hearts,” the irresistibly catchy, Fleetwood Mac-esque country-pop cut written by Hank DeVito. Newton had been playing the song at her live shows for a year before Richard Landis produced it for the album. It was all up from there: The LP went platinum in the U.S. and triple platinum in Canada, and it earned her two Grammy nominations that year. —C.D.

101

Jerry Jeff Walker, ‘Desperados Waiting for a Train’

Even back in 1970, Austin, Texas, was getting weird, and Jerry Jeff Walker — a New York transplant backed by a band called the Lost Gonzos — was leading the transition. On his 1973 live-in-Luckenbach ¡Viva Terlingua! LP, he became the first to record “Desperados Waiting for a Train,” a track that another Austin transplant, Guy Clark, wrote while working at a dobro factory in California. Moonlighting as a songwriter, he came up with the title phrase and built around it the story of a grandfather figure to whom he had once been close. “He ended up in west Texas working for Gulf Oil,” recalled Clark. “To me, as a kid, he was a real desperado, the real deal. You can’t make this shit up.” —M.R.M.