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100 Greatest Country Songs of All Time

From “Blue Moon of Kentucky” to the Paisley croon of modern Nashville

100 Greatest Country Songs of All Time

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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. But these are 100 essential songs that map out the story of country music, from Hank Williams howling at the moon to George Jones pouring one out for all the desperate lovers to Taylor Swift singing the suburban cowgirl blues.

Listen to Rolling Stone’s 100 Greatest Country Songs

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50. Steve Earle, ‘Guitar Town’ (1986)

Fueled by drugs, booze and a nasty divorce from his third wife, Steve Earle delivered this road anthem with a croon and a bark, snarling his way through lines about speed traps and truck stops with the authority of a rock & roll rebel who, at 31 years old, had already seen (and snorted) it all. Years of hard living eventually took their toll on Earle, who released three follow-ups to Guitar Town before spending the first half of the '90s in a heroin-addled haze. By the time he cleaned up his act in 1995, the alt-country movement was in full swing and Earle joined a new generation of musicians – many of whom had strummed along to a Guitar Town cassette – in the effort to tear down the boundaries between country and rock. By Andrew Leahey

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49. The Louvin Brothers, ‘The Christian Life’ (1959)

A highlight of the Louvins' second gospel album, 1959's Satan Is Real, "The Christian Life" adds a homespun fire-and-brimstone attitude to the sort of Depression-era country harmonizing picked up from earlier sibling acts like the Delmore Brothers: "My buddies shun me since I turned to Jesus / But I still love them, they burden my heart," Charlie and Ira sing in close harmony over a waltz rhythm. Almost a decade later, the Byrds went on to cover "The Christian Life" on their 1968 country-rock masterpiece Sweetheart of the Rodeo, with Roger McGuinn's voice dubbed over Gram Parsons' original lead vocal. By Richard Gehr

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48. Willie Nelson, ‘Blue Eyes Crying in the Rain’ (1975)

Fred Rose wrote it in the Forties, and everyone from Roy Acuff to Hank Williams took a shot at it, but the true purpose of "Blues Eyes Crying in the Rain" was to finally launch a long-striving, industry-beleaguered, 42-year-old Willie Nelson into orbit as the stark, startling centerpiece of his 1975 smash Red Headed Stranger. Michael Streissguth's 2013 study Outlaw: Waylon, Willie, Kris, and the Renegades of Nashville has a great scene where skittish label suits, fearful that the album "sounds like it was recorded in Willie's kitchen," frantically arrange a press listening session at Nashville hot spot the Exit/In, and then marvels as "Blue Eyes" triggers a standing ovation. "Nobody was more shocked than we were," then-CBS Records President Rick Blackburn once conceded. "It didn't have… the bells and whistles. It wasn't the way you went about making a record in Nashville in those days." Result: His first country Number One. By Rob Harvilla

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47. Bobbie Gentry, ‘Ode to Billie Joe’ (1967)

Innuendo has always played a role in folk and country music. But few songs piqued the pop crossover crowd's curiosity more than Mississippi-born, Los Angeles-schooled Bobbie Gentry's 1967 debut, in which an adolescent narrator and her family sit around the dinner table passing biscuits and gossiping about Billie Joe McAllister's descent from the Tallahatchie Bridge. McAllister threw something else off it a day earlier and Gentry never reveals what it was. "The song is sort of a study in unconscious cruelty," she once said of the family's nonchalant attitude to the suicide. Released as the B-side to "Mississippi Delta," "Ode" is a sultry country blues that drifts downstream on Gentry's ominous acoustic guitar. Arranger Jimmie Haskell added dramatic strings, and three minutes were edited from her seven-minute original. Saxophonist Lou Donaldson's funky 1967 instrumental version was sampled on dozens of hip-hop songs. By Richard Gehr

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46. Roy Acuff, ‘Wabash Cannonball’ (1936)

Complete with choo-choo sound effects and the harmonica solo of some long-imagined cowboy, Acuff's version of "Wabash Cannonball" was an early instance of country culture rising to meet the needs of city entertainment – the band even changed their name to the Smoky Mountain Boys once they made the Grand Ole Opry, presumably to retain that rural flavor. No surprise that he soon got into publishing and later ran for office – his moves always did seem a little strategic. But these are milestones, too; moments of friction in the development of a style as it took shape within the listening public at large. By Mike Powell

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45. Lefty Frizzell, ‘Long Black Veil’ (1959)

This 1959 saga of sacrifice is arguably the most persuasive primer on the pitfalls of infidelity. The hero of Frizell's saga was wrongly executed for murder; he declined to give an alibi because was spending time "in the arms" of his best friend's wife, a lethal indiscretion he takes to the grave. Since covered by Joan Baez, the Band, Johnny Cash, Bruce Springsteen and plenty of others, "The Long Black Veil" has become a country-folk standard, a grim, haunting evocation of forbidden love and all its consequences. By Amanda Petrusich

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44. George Jones, ‘The Grand Tour’ (1974)

In "The Grand Tour," the Possum sings the part of a deserted husband and father leading a stranger through a memory-filled house that is no longer a home. The genius lies in the way Jones's voice evokes that ghostly feeling amid the lush excess of producer Billy Sherrill's strings, guitars and chorus. Written by Norro Wilson, Carmol Taylor and George Richey, "The Grand Tour" is the lead and title track of Jones's masterful 1974 album. Although Jones was an admitted heavy drinker when he recorded it, "The Grand Tour" contains no clue to its protagonist's crime. Instead, there's only Jones's impossibly detailed, syllable-by-heartbreaking-syllable performance of a shell of a man condemned to life in a haunted abode that is full of stuff but devoid of love. By Richard Gehr

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43. Buck Owens and the Buckaroos, ‘Act Naturally’ (1963)

According to Owens' autobiography, Buck 'Em!, songwriter Johnny Russell stumbled into "Act Naturally" when a last minute Los Angeles recording session forced him to break a date with his Fresno girlfriend. When she asked what he would be doing, Russell gave her the line that would eventually open the song: "They're gonna put me in the movies, and they're gonna make a big star out of me." Two years and several rejections later, Owens heard Russell's demo and decided to record "Act Naturally" as part of the first sessions that brought his full road band, the Buckaroos, into the studio. Here, the group sounded tight and alive, the promise of that first line making the second – "We'll make a film about a man that's sad and lonely, and all I gotta do is act naturally" – all the more cutting. A Beatles cover helped a younger generation discover his music but Owens recalls a flight during which his neighbor explained to him how she loved the Beatles but hated country music. "As hard as I tried," he said, "I couldn't convince her that 'Act Naturally' was a country song." By Nick Murray

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42. Loretta Lynn, ‘Coal Miner’s Daughter’ (1970)

This autobiographical reminiscence was a gear-shift for Lynn, who'd made her name by feistily fending off hordes of honky-tonk homewreckers out to bed her man. The song originally rambled for six minutes and eight verses before producer Owen Bradley got out his red pen, excising a scene of Lynn's mother hanging movie magazines on their cabin wall as well as other homey details. It's country music's definitive started-from-the-bottom anthem, climaxing with one of popular music's most stirring key changes. Though Lynn is proud of her family's hardworking decency, she never pretends that her life would've been better if she'd never left Butcher Holler and poverty behind. By Keith Harris

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41. Townes Van Zandt, ‘Pancho and Lefty’ (1972)

Leave it to the poet laureate of Texas country to not only tell a story of betrayal, but to make the turncoat a sympathetic character. "Pancho and Lefty" is The Great Gatsby of country songs, conveying more about friendship, duplicity and guilt than most novels. In the song, the bandit Pancho Villa has been dispatched by the hangman's rope, but at least his suffering is over. His sidekick Lefty, who set him up, has to die a thousand deaths, trying to live with what he's done while hiding out in cheap hotels up north. Or as Van Zandt puts it, "The dust that Pancho bit down south/Ended up in Lefty's mouth." Willie Nelson and Merle Haggard's cover ended up topping the country charts in 1983. By David Menconi

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40. Gram Parsons, ‘$1000 Wedding’ (1974)

Devotees have been puzzling over the meaning of this enigmatic masterpiece for 40 years, but it has yet to yield up a definitive interpretation. 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. By David Menconi

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39. Kacey Musgraves, ‘Follow Your Arrow’ (2013)

"Even if [people] don't agree with the girls-kissing-girls thing or even the drug reference," Musgraves said about her breakthrough song, "I would hope that they would agree that no matter what, we all should be able to love who we want to love and live how we want to live." The heart of her drama lies in waiting for the establishment to catch up. Censored at the Country Music Association Awards and lionized by the Gay & Lesbian Alliance Against Defamation, 25-year-old Kacey Musgraves has become one of the loudest symbols of young country musicians embracing progressive values. But like most of her debut Same Trailer, Different Park, "Follow Your Arrow" isn't an attack on conservatism so much as an attack on any system that keeps us from being who we are, gay or straight, sober or stoned. By Mike Powell

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38. Patsy Montana, ‘I Want to Be a Cowboy’s Sweetheart’ (1935)

The first million-seller by a female country artist, this yodeling paean to the Wild West mythos made an icon of Arkansas-born singer-songwriter-actress-fiddler (and Jimmie Rodgers fan) Ruby Blevins, a.k.a. Patsy Montana. After stints in Los Angeles and New York working in radio, TV and film, Montana joined the Kentucky string band the Prairie Ramblers and adapted the early Western standard "Texas Plains" as "Montana Plains" and then as "I Want to Be a Cowboy's Sweetheart," establishing her gun-totin' cowgirl image (she later sang of being a "man-hatin' lassie" on "The She-Buckaroo"). "Cowboy's Sweetheart" has been covered consistently from Patti Page to the Dixie Chicks, even showing up on The Voice as the audition song for Gracia Harrison. By Charles Aaron

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37. George Jones and Tammy Wynette, ‘Golden Ring’ (1976)

Here's why this is country's finest duet of all time: Country's Greatest Singer and Most Feckless Drunk vs. Country's Greatest Actor and Crankiest Pill-popper. Prediction: Heartbreak wins again, in the most bluntly theatrical way possible. The couple's screwy marriage on the outs, they sound like they're about to wrap their hands around each other's throats. Inspired by a made-for-TV movie about a handgun's history – going from cop to murderer to little kid – genius co-writer Bobby Braddock subs a wedding ring for the gun. But the narrative is no less gritty, working you over like a Cassavettes flick, moving from the mundane (the intro's inexplicably frisky guitar) to the devastating (in the song's crowning scene, Wynette voices the man's palpable hurt, while Jones intones grimly, "She says one thing's for certain, I don't love you anymore"). The ring ends up back in the Chicago pawn shop from whence it came. Our protagonists, meanwhile, remain a dizzy gospel-invoking mess. By Charles Aaron

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36. Hank Williams, ‘Lost Highway’ (1949)

The song that possibly best articulates the doomed country mythos that Hank Williams' life and death epitomize wasn't written by Hank himself. The blind country singer-songwriter Leon Payne wrote and recorded "Lost Highway" just a year before. Payne wasn't just waxing spiritually metaphorical: He was indeed lost along the highway, struggling unsuccessfully to hitchhike from California to Texas to visit his ailing mother, forced instead to seek food and shelter in a Salvation Army. By Keith Harris

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35. The Everly Brothers, ‘Bye Bye Love’ (1957)

Recorded with an all-star band that included Elvis' piano player, the Opry's house drummer and guitarist Chet Atkins, "Bye Bye Love" catapulted the Everly Brothers into the stratosphere, becoming a Top Five hit on the country, pop and R&B charts in 1957. Apart from the song's introductory guitar riff, which Don Everly lifted from an earlier tune called "Give Me a Future," the brothers didn't write "Bye Bye Love." They did give the song its identity, though, beefing up a relatively standard chord progression with equal doses of Tennessee twang and their iconic harmonies. By Andrew Leahey

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34. The Carter Family, ‘Wildwood Flower’ (1928)

Originally an 1860 parlor song titled "I'll Twine 'Mid the Ringlets" (a raven-tressed maiden's plucky response to being unceremoniously abandoned), "Wildwood Flower" was revived by Virginia "song catcher" A. P. Carter. He arranged it for his family trio including singer-autoharpist wife Sara and her lead-guitarist cousin Maybelle, who turned 19 the day the group recorded the song outside Philadelphia. Its opening lyrics were mondegreened, pursuant to the mishaps of oral tradition. "I'll twine mid the ringlets of my raven black hair" became "Oh, I'll twine with my mane, golden weeping black hair," and would continue to alter as numerous others recorded it – including Joan Baez, Emmylou Harris and Reese Witherspoon. No version, however, is quite so outlandish as country comedian Dan Bowman's hallucinogenic 1964 variation, "Wildwood Weed." By Richard Gehr

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33. Porter Wagoner, ‘A Satisfied Mind’ (1955)

"One day my father-in-law asked me who I thought the richest man in the world was, and I mentioned some names," says co-writer Red Hayes. "He said, 'You're wrong, it is the man with a satisfied mind.'" Porter Wagoner's demo of this pious lament, first recorded at a Missouri radio station in 1954, would end up becoming the version that would hit Number One on the country charts the following year. In the ensuing decades, the most famous song by the man once known as Mr. Grand Ole Opry would go on to become an unlikely standard amongst a slew of rootsy country-rock revivalists: the Byrds, Bob Dylan, Gram Parsons, David Allan Coe, Lucinda Williams and Jeff Buckley have all taken their turn at the song. By Jonathan Bernstein

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32. Mississippi Sheiks, ‘Sitting on Top of the World’ (1930)

Not so much straight "country" as the blues seasoned with rural fiddle, "World" percolated through the western swing circuit as covered by Bob Wills and Milton Brown; became Fifties blues in the hands of Howlin' Wolf; and then Sixties rock via the Grateful Dead and Cream – a history that, if nothing else, cements the song as a kind of Rorschach test that ultimately filtered back to Chet Atkins, the Nitty Gritty Dirt Band and Willie Nelson. More recently, the Mississippi Sheiks became a cause for Jack White, who is reissuing their entire catalog through his Document label – presumably lured by that "real-thing" feel in their gritty but obscure sound. By Mike Powell

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31. Hank Williams, ‘Your Cheatin’ Heart’ (1953)

Did Hank Williams write perhaps his greatest "heart" song to spite his first wife, while joyriding in a convertible and eating ice cream with his second wife? Wife No. 2 says so, but she probably would. At any rate, Williams was in full flail at the time, caught in a matrix of loves: Audrey (ex-wife-manager, mother of his son); Bobbie (pregnant girlfriend contractually promised child support); Billie Jean (19-year-old new wife). It's not hard to imagine that the owner of the cheatin' heart was the guilt-wracked singer himself. While Don Helms' mournful pedal steel pierces the air, Williams sorrowfully laments a cheater's fate. Completed in a single take during his last recording session, it was released posthumously and went straight to Number One. By Charles Aaron

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30. Faron Young, ‘Hello Walls’ (1961)

Lore has it that "Hello Walls" songwriter Willie Nelson once met up with Lefty Frizzell for a collaborative session, but when Frizzell took a break and left the garage where they were sitting, Nelson got the idea for his first major hit. When voiced by friend Faron Young, a.k.a. the "Hillbilly Heartthrob," the song took on a particular elegance, going to Number One on the country chart, and even becoming a Number 12 pop hit. In the storied country-song tradition, "Hello Walls" possesses a wit that makes you wince: Like a character in a one-act play, the heartbroken singer literally speaks to the walls, window and ceiling of an empty room, asking pitifully, "I bet you dread to spend another lonely night with me." By Charles Aaron

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29. Jimmie Rodgers, ‘Blue Yodel No. 1 (T For Texas)’ (1928)

A phenomenon that created country music's very first superstar, the first of 13 yodeling records by "the Singing Brakeman" Jimmie Rodgers began three months after a middling session in Bristol, Tennessee with a traveling record exec named Ralph Peer – the sessions, in a former hat factory, also captured the Carter Family for the first time. Jimmie Rodgers tracked Peer to New York and he soon ended up in Camden, New Jersey, where he recorded the song that defined his legacy. What was it about Rodgers' yodel? Slippery but controlled, despairing but casual, refined but so strange it seemed to have been beamed him from some distant star – it was the sound of pain made charming, even sweet. If he was really planning to buy a pistol and shoot poor Thelma "just to see her jump and fall," he would probably need to pick up the pace. By Mike Powell

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28. Hank Williams, ‘I Saw The Light’ (1948)

Hank Williams was better known for seeking earthly pleasures in Saturday night honky-tonks than for belting out promises of salvation on Sunday morning. But this gospel redemption number was his longtime show-closer, an upright happy ending to the pageant of sin and sorrow that preceded it. Fans so strongly identified Williams with the song that when a 1953 Canton, Ohio crowd waiting for the star's long overdue arrival disbelieved the announcement of his death, "I Saw the Light" was what Hawkshaw Hawkins sang in tribute to convince them that the sad news was indeed true. By Keith Harris