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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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100

100. Brad Paisley, ‘Welcome to the Future’ (2009)

Mainstream country's most prominent liberal ambitiously overloads this nearly six-minute single from 2009's American Saturday Night, explaining that he wanted "to serve up a little multigenerational truth with a strong sense of hope and possibility." In this bright "Future," Paisley marvels at car DVD players and mobile-phone videogames, imagines how trans-Pacific commerce might amaze his WWII-vet grandfather and then brings his mid-tempo country-rocker down a notch to appreciate the racial progress that has occurred in his own lifetime – he debuted the song live at the White House. Basically, it's a typical Brad Paisley A.D.D. special, mixing synth lines with steel guitar, fiddle breaks with speed riffs and sense with sentiment. By Richard Gehr

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99

99. Harry Choates, ‘Jole Blon’ (1946)

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 charts. "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, 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. By Reed Fischer

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98

98. C.W. McCall, ‘Convoy’ (1975)

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 C.B. radio, gave Iowa singer C.W. McCall the only Number One hit of his career, sold two million copies, started a C.B. 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 C.B. radios," explained McCall, who co-wrote the song with Chip Davis. "They had a wonderful jargon. Chip and I bought ourselves a C.B. radio and went out to hear them talk." That's a 10-4, good buddy. By Jonathan Bernstein

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97

97. Gretchen Wilson, ‘Redneck Woman’ (2004)

Originally a collective of Nashville outcasts and outsiders known for their open-minded open mic night, the MuzikMafia went mainstream with the twin successes of Big & Rich's "Save a Horse (Ride a Cowboy)" and Gretchen Wilson's "Redneck Woman." With its upbeat swing and beer-drinking, Walmart-wearing identity politics, "Redneck Woman" quickly rose up the charts. Following a breakthrough performance at the 2004 Country Radio Seminar, "Redneck Woman" became the fastest rising Number One since Billy Ray Cyrus' "Achy Breaky Heart." Though Wilson herself was never able to repeat its success, the song paved the way for rocking female bad-asses like Miranda Lambert and Kimberly Perry. By Nick Murray

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96

96. Ronnie Milsap, ‘Smoky Mountain Rain’ (1980)

This story of returning home from the city was told through thunderous piano playing (inspired by Milsap's session work on Elvis' "Kentucky Rain") and producer Tom Collins' spiralling 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 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. By Nick Murray

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95

95. Bellamy Brothers, ‘Old Hippie’ (1985)

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 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"? By Keith Harris

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94

94. Dwight Yoakam, ‘Guitars, Cadillacs’ (1986)

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, L.A. was the perfect place for the Ohio transplant. A home for country rock since the Byrds and the 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 bassline, 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." By Nick Murray

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93

93. Tom T. Hall, ‘Old Dogs, Children and Watermelon Wine’ (1972)

In 1972, country music's consummate storyteller traveled to Miami Beach to perform at the Democratic National Convention that nominated George McGovern and returned to Nashville afterward with a soon-to-be-hit. A janitor, a month away from his 66th birthday, shared his impressions of the only three things worth a damn in life, while casting aspersions on the loyalty and value of lovers and friends – and Hall took it all down. The resulting hit, though sentimental on the surface, has a cynical flipside, its distrust of all but the simplest things in life imparting an aftertaste of sour Seventies disillusion. Nixon won, by the way. By Keith Harris

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92

92. Juice Newton, ‘Queen of Hearts’ (1981)

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-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 LP. It was all up from there: The LP went platinum in the U.S. and triple platinum in Canada and earned her two Grammy nominations that year. By Cady Drell

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91

91. Garth Brooks, ‘Friends in Low Places’ (1990)

With a voice stirring together the low end of Johnny and the high whine of Hank, Garth Brooks was just beginning his historic superstar run. A couple dozen folks – including "Low Places" songwriters Dewayne Blackwell and Earl "Bud" Lee – partied in the studio to create the bar-storming romp heard on the final refrain. But the party was just starting. The hit helped Brooks' second album, No Fences, ship 17 million copies in the U.S. – still one of the 10 best-selling albums of all time. When Brooks performed "Friends in Low Places" on the Grammys in the early Nineties, the stage was set up like a posh black-tie affair. Just as the song says, the Oklahoma native showed up in boots – as well as a vertical striped shirt, black cowboy hat, and a thumb jabbed into the pocket of his jeans. Eventually the onstage glitz got pushed away to reveal a down-and-dirty saloon, like the ones blasting his song nationwide. By Reed Fischer

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90

90. Ray Wylie Hubbard, ‘Redneck Mother’ (1975)

This second-tier Texas outlaw still writes, performs and records, but he 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." By Keith Harris

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89

89. Gary Stewart, ‘She’s Actin’ Single, I’m Drinkin’ Doubles’ (1975)

A hurtin', cheatin', drinkin' trifecta, Gary Stewart's only Number One would pass for a honky-tonk parody if the Kentucky singer's trembling tenor weren't so convincing. A hardcore-country home run at a time when the genre was heading uptown, "She's Actin' Single" finds Stewart living a perpetual nightmare in which "she pours herself on some stranger" while "I pour myself a drink somewhere." The Wayne Carson–penned tune was the third hit from Stewart's excellent Out of Hand, and the record features both John Hughey playing tear-jerking pedal steel and a mournful chorus from Elvis-affiliated gospel quartet the Jordanaires. An unreconstructed Southern rocker when he wanted to be, Stewart's version of a self-pitying coward struck a chord with a jukebox crowd who sometimes, as Stewart sang elsewhere, "got this drinkin' thing, to keep from thinkin' things." By Richard Gehr

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88

88. Jerry Jeff Walker, ‘Desperados Waiting for a Train’ (1973)

Even back in 1970, Austin 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." By Marissa R. Moss

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87

87. Lyle Lovett, ‘If I Had a Boat’ (1988)

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 too. 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. By Keith Harris

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86

86. Donna Fargo, ‘The Happiest Girl in the Whole U.S.A.’ (1972)

Triumphant, hopeful and as corny as Kansas in August, North Carolina native Donna Fargo took this self-composed paean to young newlywed bliss to the top of the country charts. There's no tortured dark-end-of-the-street sentiments for Fargo, who seems to mean every last "skippidy do da." All that honky-tonk ne'er-do-well stuff about drinkin' and cheatin' and carryin' on? That's for middle age. For the two-and-a-half minutes that this lovers' anthem lasts, it can wait. By David Menconi

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85

85. O.B. McClinton, ‘Don’t Let the Green Grass Fool You’ (1972)

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 R&B hit "Don't Let the Green Grass Fool You," which notched Number 37 on the country charts. Originally an early Wilson Pickett single, the perspective of an about-to-be-jilted lover trying to spark that old flame resonates in any genre. By Reed Fischer

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84

84. Neko Case, ‘People Got a Lotta Nerve’ (2009)

Who cares that the song's two protagonists – a killer whale and an elephant – were two unusual subjects for a country song? "I realized that it's OK to admit that no matter who your characters are, you're writing about yourself," Neko Case told the New York Times. The first single from 2009's Middle Cyclone, "People Got a Lotta Nerve" sent a stern warning to anyone foolish enough to tie the singer down. "I'm a man-, man-, maneater," went the chorus, delivered with such poppy playfulness that it was easy to gloss over the song's sinister undertow. By Andrew Leahey

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83

83. Bobby Bare, ‘Streets of Baltimore’ (1966)

This tragic tale of a man who gave up his entire life to make his woman happy in Baltimore (and who gets subsequently dumped there) was originally recorded by Bobby Bare, a singer most famous for working with a young Kris Kristofferson. But, as Bare told Rolling Stone in 1980, "Most of my hits would have been hits for anybody, I just got to 'em first." So it was with "Streets of Baltimore," penned by Tompall & the Glaser Brothers, who wanted to release the single themselves in September of 1966. Unfortunately for them, Bare got to it first (in June) and scored a hit, reaching the Number Seven spot on the country charts. The joke ended up being on Bare, though: For many, Gram Parsons' 1973 version is widely considered the song's most essential incarnation. By Cady Drell

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82

82. Reba McEntire, ‘Fancy’ (1991)

Written and recorded for Bobbie Gentry's 1969 album of the same name, "Fancy" tells a rags-to-riches tale of a young girl whose mother sends her into prostitution. McEntire had wanted to record the song for years, but producer Jimmy Bowen argued against it – not because of the subject matter, but because he felt too many people associated the song with its original performer. When McEntire turned to Tony Brown for her 1990 album, Rumor Has It, the pair gave the song a striking loud-quiet-loud arrangement that helped introduce it to a new generation. By Linda Ryan

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81

81. Gary Allan, ‘Songs About Rain’ (2003)

The second single from Allan's See If I Care tells of a downtrodden masochist who's wasting a perfectly good night driving in circles, listening to a perverse radio station that for some reason keeps playing songs – "Rainy Night In Georgia," "Kentucky Rain," "Here Comes That Rainy Day Feeling Again," "Blue Eyes Crying in the Rain" – that all tell of stormy weather. But where the heartbroken man wallows in these tracks, Allan is busy placing his own in their lineage, successfully conjuring a country classic that's as heartbreaking as the sum of its references. Co-writer Liz Rose, who has since helped pen a handful of hits by Taylor Swift, would later recall how "Songs About Rain" changed her career: "It wasn't until I had the Gary Allan single that I could really say I was a songwriter." By Linda Ryan

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80

80. John Anderson, ‘Wild and Blue’ (1982)

Inspired by a girl who "could party and rock harder than anyone I'd known," John Scott Sherrill wrote this song while separating from his wife. The first country chart-topper for both singer John Anderson and Sherrill, "Wild and Blue" is a hauntingly beautiful account of a cheating woman, told from the POV of her cuckolded man. Anderson's syrupy drawl and mournful wail is intensified by sister Donna's Hill Country harmonizing. Lloyd Green's pedal steel and twin fiddles paint a long, bleak evening of waiting for honey to come home, but in the end the singer's resigned forgiveness is hardly cause for celebration. Big-voiced Sally Timms gave Anderson's 1982 hit a straight, strong reading when British country-punks the Mekons covered it on 1991's Curse of the Mekons. By Richard Gehr