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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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58. Jeannie C. Riley, ‘Harper Valley P.T.A.’ (1968)

"That song was my novel," songwriter Tom T. Hall once said of the epic "Harper Valley P.T.A." In this sassy 1968 takedown of small-town hypocrisy, a mini-skirted widow "socks it to" the titular busybodies – in its way, it was as innocence-ending as Bobbie Gentry's "Ode to Billie Joe" the previous year. Indeed, when singer Margie Singleton asked Hall to write her a similar song, the aspiring novelist took note of the Harpeth Valley Elementary School in Bellevue, Tennessee and found artistic inspiration in Sinclair Lewis's religion-mocking novel Elmer Gantry. Jeannie C. Riley's recording, however, made her the first woman to top both Billboard's Hot 100 and country-singles charts. Barbara Eden starred in both the 1978 comedy based on the song and in a 1981-82 TV show spun off the flick. By Richard Gehr

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57. Eric Church, ‘Springsteen’ (2011)

It's not really about Bruce Springsteen, first of all. Though stadium-filling bad boy Eric Church's iPhone-lighter-app-waving triumph details "a love affair that takes place in an amphitheater between two people," the Boss was not the performer in question. Church politely but firmly declines to reveal the actual inspiration, which means the best country song of the 2010s thus far might have more accurately been titled "Nugent" or "Anka" or "Fogelberg." Cowritten by Church with Jeff Hyde and Ryan Tyndell, it's a dreamy, nostalgic weeper (tough as our man talks, he's a softie at heart) and drove 2011's Chief to dizzying heights. It even earned Church a handwritten thank-you note from Springsteen himself – scrawled on the back of a Fenway Park set list. By Rob Harvilla

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56. Carrie Underwood, ‘Before He Cheats’ (2006)

This crossover smash emerged from circumstances as prefabricated as country music gets – written and produced by men whose credits include Lady Antebellum and Rascal Flatts, sung by an American Idol winner and sporting a literal-interpretation video. And yet the popcraft of "Before He Cheats," as rendered by Carrie Underwood in the key of frosty rage, is nearly perfect. Even a certified alt-country critical darling like Canadian singer-songwriter Kathleen Edwards is not immune to its seductive charms. "The rhythm of it, the metric of the lyrics, the chord changes, the play on words and unconventional patterns, the way she says 'Shania karaoke' – it's genius," Edwards said in 2009. "Fuck, I wish I'd written that!" By David Menconi

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55. The Flatlanders, ‘Dallas’ (1990)

Perpetually unsung, the Flatlanders were a Lubbock trio who sounded like – well, there was Jimmie Dale Gilmore's flat, twangy voice; the warble of a singing saw; the lyrics that made sutras of psychedelic complexity sound like they were something Grandma crocheted into a throw pillow. Small-town, but more importantly, sensitive enough to address even the most routine insults of life in the 20th century, the big city didn't repulse them, but it did give them the willies. And yet in song, they are somehow always the eye of a storm: unchanging, know-nothing, happy to breathe deeply and just watch the show unfold. Would you be surprised to learn that they sank like a stone? By Mike Powell