The 200 Greatest Country Songs of All Time

Clint Black spent years playing empty bars around Houston, making a living working construction and cutting bait, until he finally broke through with his 1989 album, Killin’ Time. With his cocky grin and black hat, Black debuted the same year as his fellow neo-trad outsider Garth Brooks, both guys setting the pace for the imminent Nineties country explosion. “Killin’ Time” is old-school honky-tonk melodrama, written by Black with longtime collaborator Hayden Nicholas. He sings about drowning his sorrows on the barroom floor, in a boozily existential showdown with death. It was the second-biggest country hit of 1989 — right behind another Black hit, “A Better Man.” —R.S.

Supergroup projects are often inspiration-starved one-off cash grabs. Not Pistol Annies, who crowned their third sharp album with this hilariously sassy anthem of born-again singledom, a candidate for their best track to date. It was written by Miranda Lambert, ready to laugh a bit after her 2015 high-profile divorce from Blake Shelton and her soul-searching 2016 The Weight of These Wings, one of the most potent breakup albums ever made. But Lambert’s co-Annies, Angaleena Presley and Ashley Monroe, knew plenty about divorce, too — Presley first-hand — and together the trio turned the track into a campy roadhouse rocker with a Tennessee Two chug that peaks with their gleeful unison shout: “I broke his heart and I took his money!” That the song effectively renewed the vows of a partnership outlasting two of their marriages made its badass sisterhood that much sweeter. —W.H.

When Sturgill Simpson dropped Metamodern Sounds in Country Music in 2014, his ornery sense of independence made him a perfect anti-hero in the era of bro country. But he was no standard outlaw. “Turtles All the Way Down” landed somewhere between classic country and psychedelia, taking its title from a proverb about the lack of meaning at the base of existence. Simpson got his point across with acid-soaked guitars, visions of Jesus in flames, and a baritone that could put the fear and love of God into you all at once. “It is still a beautiful idea,” Simpson told Rolling Stone at the time, “that everything is being emitted from one point and that we’re all this universal shared consciousness.” —J. Gage

Deana Carter’s coming-of-age ballad about summer romance on a farm was a hit in 1996, but over time it’s evolved into a country standard, your go-to karaoke song where you cringe during the line “I still remember when 30 was old.” Co-written by Matraca Berg and Gary Harrison, the song was named after the wine cooler Boone’s Farm Strawberry Hill. “‘Strawberry Wine’ was my story,” Carter told Rolling Stone in 2016. “It’s her story, it’s my story, it’s all the fans’ story. We recorded it, and they put the steel guitar on the front to countrify it a little bit. They wanted to take the bridge out, and that was a huge fight because they thought it was too Beatles and too risky, but I wouldn’t budge.” We’re glad she didn’t. —A.M. 

Texas artist Jessi Colter’s forlorn intensity imbued this tale of a woman left in the shadow of her lover’s dead ex with lived-in heartache, carried by a funereal melody she played herself on piano. With an extended instrumental intro, a verse, and two choruses, the song made for an unlikely hit, but topped the country chart and reached the Top Five of the Billboard Hot 100, appealing in equal parts as an easy-listening and pop singer-songwriter ballad. Virtually overnight, Colter was selling more records than her boyfriend at the time, Waylon Jennings, and “I’m Not Lisa” became a standard in its own right, tackled by the likes of Lynn Anderson, Faith Hill, and Marianne Faithfull. —J. Gage

Despite a tragically short career, Keith Whitley left an indelible footprint on country music before his death from alcohol poisoning in 1989 at age 33. As a teenage bluegrass picker, he was good enough to join Ralph Stanley’s band. And as a singer, his resonant tone was unmatched. “I’m No Stranger to the Rain,” the last single released before his death, showcases Whitley’s distinct voice and the stellar songwriting of Sonny Curtis and Ron Hellard. “I’ll put this cloud behind me,” Whitley declares, “that’s how the man designed me/To ride the wind and dance in a hurricane.” It’s a remarkable recording, full of defiance and a little bit of bittersweet resignation — just like Whitley himself. —J.H.

When Atlanta rapper-producer Lil Nas X’s debut single, “Old Town Road,” landed on Billboard’s Hot 100 chart, the Hot Country Songs chart, and Hot R&B/Hip-Hop Songs chart all at once, his outrageously catchy riff on “hick-hop,” and its remix with Nashville veteran Billy Ray Cyrus, quickly reanimated the zombie corpse of the “Is it country?” debate. Some of that chatter was just thinly veiled or even outright racism, but none of that detracted from the song itself, which fused banjo twang and rattling bass into an undeniable banger, with an unforgettable chorus and clever lyrics to boot. —B.M.

Dwight Yoakam is often painted as a critic of Nashville, but in “Guitars, Cadillacs,” the hillbilly music that Tennessee once produced becomes the only thing that makes Tinsel Town tolerable for this “naive fool who came to Babylon and found out that the pie don’t taste so sweet.” Of course, despite his posturing, Los Angeles was the perfect place for the Ohio transplant. In L.A., home for country-rock since the Byrds and the Flying Burrito Brothers, the ambitious singer found his match in local roots-oriented, post-punk acts like the Blasters, Lone Justice, and the Knitters. The biggest influence on “Guitars, Cadillacs,” however, the one who lent the song its crisp guitar and walking bass line, remained two hours north. His name was Buck Owens, and two years later, Yoakam would give him his 21st chart-topper with “Streets of Bakersfield.” —N.M.

After periods emulating both smooth Eddy Arnold and honky-tonkin’ Hank Williams (whose Drifting Cowboys band he led after Williams’ death), Ray Price (a.k.a. “the Cherokee Cowboy”) returned to his Texas roots with this 1956 megahit that spent 20 weeks at the top of Billboard‘s country chart. Co-writer Ralph Mooney penned the tune after his wife left him due to his drinking, and its lyrics suggest deep emotional delirium and paranoia. The music, however, reflected Price’s new shuffle style, with single-string fiddle, pedal steel guitar, and doubled acoustic and electric basses. Six months after Price’s release, Jerry Lee Lewis’ first Sun Records side was a more blatantly delirious rock cover that turned many heads. —R.G.

Alison Krauss — a brilliant singer and bluegrass fiddle prodigy who had a record deal before she was 15 — wasn’t widely known for years. That changed when Rounder Records issued a compilation of old tracks by her virtuoso string band Union Station, plus side projects and covers, under Krauss’ name alone in 1995. The highlight was her version of the Foundations’ 1967 soul-pop hit “Baby, Now That I’ve Found You,” a swaggering love pledge she flipped into delicate, James Taylor-meets-Dolly Parton pillow talk. It fluttered up to the country chart’s top tier, borne on Krauss’ pristine soprano, and earned her the first of many Grammys — so many, in fact, she had a reign as the Grammys’ most-awarded woman until Beyoncé dethroned her in 2021. —W.H.

In the mid-Eighties, Lyle Lovett emerged on the bookish, folkie fringe of a new traditionalism that reacted against the pop leaning of the Urban Cowboy era. Consisting of little more than guitars — a finger-picked acoustic and a welling slide — “If I Had a Boat” is nothing to ride a mechanical bull to. And the abstract lyrics, which imagined Roy Rogers as confirmed bachelor and Tonto losing patience with the Lone Ranger, demanded concentration. Absurdist and meditative as it is, “If I Had a Boat” arose from a true story. Lovett claims he once tried to ride a pony across a pond. He wished he’d had a boat. —K.H.

This tragic ballad for the ages launched the solo career of a woman who certainly knew tragedy: Her pioneering country duo the Davis Sisters ended when a car wreck killed singing partner Betty Jack Davis. For this classic recording, Skeeter (born Mary Francis Renick) was joined by piano legend Floyd Cramer in Nashville’s RCA Studio B, with producer Chet Atkins behind the glass. It was a crossover smash in 1963, and it would be widely covered by acts from Herman’s Hermits to Patti Smith. But no one has bettered the original, which resonates to this day: See the John F. Kennedy assassination episode of Mad Men, in which the song clocks what may be the most powerful musical moment in the show’s whole run. —W.H.

A blizzard kept songwriter Danny Flowers inside an Oklahoma hotel while on tour with Don Williams, and Flowers wrote this country-funk classic in about 30 minutes. Williams took an immediate liking to it — but so did Eric Clapton when they met up with the guitarist in Nashville. Williams and Clapton playfully bickered over who got to record the song first. “I just put both hands up and said, ‘Stop! If you are going to fight about it, I’m not going to let either one of you do it,’” Flowers told Tulsa World. While a live recording of Clapton’s driving barrelhouse rock version became a minor pop hit, it was Williams’ uniquely grooving disco-twang version that would hit Number One on the country chart. —C.W.

“I think he was a bit tortured,” said Rosanne Cash about Don Gibson. “And he had somewhat of a difficult life, and all of his experience, and his longing and his own heartbreak is really apparent in his vocals.” “Sea of Heartbreak” was one of the rare songs Gibson didn’t write himself, its gloomy nautical metaphor coming courtesy of Hal David and Paul Hampton, inspired by the latter’s stormy divorce. Gibson’s interpretation remains the definitive one, but the song would reenter the country chart many times. “Sea of Heartbreak” eventually took a new life in the Nineties when Johnny Cash recorded it with Tom Petty and the Heartbreakers. Said daughter Rosanne, “You know, not being disloyal, but I have to say, I still prefer the Don Gibson version.” —C.W.

These irresistibly slick opportunists always had a keen eye for cultural shifts: “If I Said You Had a Beautiful Body Would You Hold It Against Me” treated country’s late-Seventies transition from the honky-tonk to the singles’ bar as a forgone conclusion, and 1987’s “Country Rap” is pretty self-explanatory. “Old Hippie” is the Bellamy Brothers’ astute take on how onetime counterculture rebels, alienated by disco and New Wave, turned to country music in the Eighties with an age-worn weariness: “He ain’t tryin’ to change nobody/He’s just tryin’ real hard to adjust.” Ten years later, “Old Hippie (The Sequel)” brought us into the Clinton era, and in 2007, on “Old Hippie III (Saved),” our hero was born again. Meanwhile, contemporary country is providing a similar escape for many aging Nineties rock fans. Who’s going to write “Old Slacker”? —K.H.

Trisha Yearwood’s debut hit opens with a girl named Katie sitting on her front porch “watching the chickens peck the ground.” That line may seem incidental to the song’s multi-generational story of love, escape, rebellion, and soft-serve ice cream, but for writer Jon Ims, its depiction of rural boredom was the center of the song. It took him 32 drafts to get the rest right. The climax, when Katie’s mom sees herself in her daughter’s relationship, came from an experience Ims himself had in his early 20s. “I just liked the story, and that’s a big reason why it’s been successful,” said Yearwood. “Everyone can relate to one of the characters.” —N.M.

After failed attempts at R&B, country pastures were far greener for Osbie Burnett McClinton. Once the Mississippi native became the “Chocolate Cowboy” in the early Seventies, he rolled out a string of charting country hits featuring his rich baritone voice, able backup singers, and a wry sense of humor. (“The Other One” corrected anyone mistaking him for Charley Pride.) McClinton’s biggest song, off 1972’s Obie From Senatobie (via Stax subsidiary Enterprise), was a twangier remake of the R&B hit “Don’t Let the Green Grass Fool You,” which reached Number 37 on the country chart. Originally a Wilson Pickett single, the song’s perspective of an about-to-be-jilted lover trying to spark that old flame resonates in any genre. —R.F.

“There Stands the Glass” is a perfect example of the kind of country song that makes drinking sound much more like a job than an adventure. Webb Pierce, a legendary honky-tonk voice who all but owned 1950s country radio, parked this ode to the bottle at Number One on the country chart for three months in 1953. It’s been covered by everyone from Loretta Lynn to indie-rocker Jon Spencer, including a 1982 version where an older Pierce duets with Willie Nelson. Few songs in any genre have put the cycles of self-pity and addiction more directly: “There stands the glass, fill it up to the brim/ Until my troubles grow dim, it’s my first one today.” It will absolutely, positively not be his last. —J. Gross

For her debut single, a 15-year-old Taylor Swift bottled up nostalgia and put it in a song. “Tim McGraw” opens against a twinkling arpeggio with a couplet that felt wise beyond Swift’s teen capabilities despite being written in her high school math class: “He said the way my blue eyes shined/Put those Georgia stars to shame that night/ I said ‘That’s a lie.’” The 2006 track is both a touching love letter to “a boy in a Chevy truck” and an ode to the power of country music itself. Swift tapped memories she associated with McGraw’s “Can’t Tell Me Nothin’,” and cleverly structured her song like a McGraw tune, creating her own contribution to the canon of wistful country songs. —M.G.

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   

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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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.  

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

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.

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.