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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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13. Bill Monroe and The Blue Grass Boys, ‘Blue Moon of Kentucky’ (1947)

As the master builder of bluegrass, Bill Monroe took the fiddle music he learned on the Kentucky farm of his childhood, tricked it out with blues, gospel and swing, then stepped on the gas with his meticulously on-point band the Bluegrass Boys (led by Earl Scruggs). But his signature tune was timeless, beyond genre, a waltz featuring Monroe on mandolin and falsetto testifying, speaking straight to country folk about a blue moon guiding him back home, not bestowing bad luck. As Monroe told NPR in 1983: "It's got Baptists and Holiness and Methodists singing in it and Scotch bagpipe and the old Southern blues… It really touches your heart, and it's a good, clean music." Ironic, then, that Elvis Presley's jacked-up 4/4 version seven years later jet-propelled his taboo-busting career, and by extension, rock & roll itself. By Charles Aaron

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12. Buck Owens and the Buckaroos, ‘I’ve Got a Tiger By the Tail’ (1964)

This hilarious tune about a hard-partying woman is powered by a wiry guitar style that influenced the Beatles and the Byrds. An essential example of the spunky Bakersfield sound that toughened up Sixties country. The idea for the single came to the singer during a drive with legendary songwriting partner Harlan Howard. Upon noticing a sign with the Esso gas slogan "Put a Tiger In Your Tank," Owens said to Howard, "How about 'Tiger by the Tail' for a title?" Howard jotted down some lyrics in the backseat, Owens improvised a melody on the spot, and the song was complete before the trip was over. Howard, who considered "Tiger" a novelty tune, was skeptical of the song's potential, but "Tiger" proved to be Owens' biggest hit to date, quickly reaching Number One on the country charts and eventually providing the Nashville establishment outsider with the first (and highest charting) crossover pop single of his career. By Jonathan Bernstein

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11. Stanley Brothers, ‘Man of Constant Sorrow’ (1951)

With likely origins as a 19th-century Baptist hymn, "Man of Constant Sorrow" was revived by the Stanley Brothers in 1951; covered by Joan Baez, Bob Dylan and Judy Collins in quick succession a decade later; and launched a full-on Americana revival with its prominent placement in the Coen Brothers' O Brother, Where Art Thou? in 2000. Its ambiguous provenance can be attributed to blind Kentucky fiddler Dick Burnett, who published it in 1913 as "Farewell Song" and, when asked its origin, replied, "I think I got the ballad from somebody… I dunno. It may be my song." Ralph Stanley heard his daddy sing a version, which he and brother Carter added words to and transformed into a high, lonesome landmark of post-breakup misery and transient unease. By Richard Gehr

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10. Waylon Jennings and Willie Nelson, ‘Mammas, Don’t Let Your Babies Grow Up to Be Cowboys’ (1978)

The best buddy team in country history took the cowboy song tradition of Roy Rogers into the Seventies, with a front-porch charisma that any doctor or lawyer would be lucky to have. Songwriter Ed Bruce's version of this cautionary tale, released in late 1975, became a minor country hit. But shortly thereafter, Waylon and Willie took the song to Number One. Their combined star power and road-weary charm romanticized the emotionally inaccessible male drifter more powerfully perhaps than any country song had before. Despite the combined efforts of the singers' and countless mammas, however, the years since have seen no marked decline in baby-to-cowboy transformations. By Keith Harris

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9. Dolly Parton, ‘Jolene’ (1973)

Inspired by the sight of her husband flirting with a bank teller, "Jolene" is Parton's most heartrending triumph and the most devastating cheating song of them all. These days, contemporary country charts are overloaded with blustery assertions of self-sufficiency – from Marina McBride to Miranda Lambert – which makes it even more heartbreaking to hear one of country's most beloved matriarchs sounding so vulnerable. "Jolene," a hit for Parton in 1973, sees her imploring another woman to leave her man alone. By Amanda Petrusich

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8. Merle Haggard, ‘Mama Tried’ (1968)

No one could write a prison number like ex-con Merle Haggard. Despite its humble origin as a commission for Killers Three, a B-movie produced by and starring Dick Clark, this 1968 Platonic ideal of a country song turned out to be the Hag's most autobiographical statement. With its James Burton dobro vamp and haiku-like Roy Nichols Fender solo, "Mama Tried" is a celebration of cussed stubbornness disguised as an apology. Haggard was indeed sent to San Quentin in 1957, but "instead of life in prison I was doing one-to-15 years," he told a reporter. "I just couldn't get that to rhyme." Oddly upbeat compared to his earlier "Sing Me Back Home," "Mama Tried" was adopted by perennial band-on-the-the-run the Grateful Dead, who performed it at Woodstock and on more than 300 subsequent occasions. By Richard Gehr

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7. Ray Charles, ‘You Don’t Know Me’ (1962)

This Cindy Walker-penned gem was pulled from about 250 country tunes Ray Charles considered for his 1962 album, Modern Sounds in Country and Western Music. Backed by a chorus and sumptuous strings, Charles constructs a lump in his throat and an ache in his heart while working his jazz and R&B expertise into "hillbilly" material. "[T]he words to country songs are very earthy like the blues, see, very down," he once told Rolling Stone. "Country songs and the blues is like it is." Elvis Presley, Bob Dylan and Willie Nelson all went on to cover what became a Number Two pop hit for Charles, but a somber version by Richard Manuel of the Band comes closest to reliving this version's woes. Modern Sounds galvanized racial integration in the music industry, made Nashville songwriters the hottest of the time, and showed Charles exercising artistic control unprecedented for black artists at the time. By Reed Fischer

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6. Tammy Wynette, ‘Stand By Your Man’ (1968)

A family-values tract with its share of contradictions (Wynette was a four-time divorcée). But there’s no mistaking the power in her voice or the beauty in Billy Sherrill’s lush production. Many heard her signature tune, written with producer Billy Sherrill, as a reactionary riposte to the then-emerging women’s liberation movement, rendering the song inextricable from the Baby Boomer culture wars. In 1992, Hillary Clinton even referred to it disparagingly when a 60 Minutes interview confronted her with questions about her husband’s infidelities. Wynette later said she spent 20 minutes writing this and 20 years defending it. By Keith Harris

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5. Jimmie Rodgers, ‘Standing on the Corner (Blue Yodel #9)’ (1930)

By 1930, the tuberculosis-stricken former railroad worker and blackface performer Jimmie Rodgers was a certified star, his "blue yodels" selling millions. But the "Father of Country Music" was also a mercurial, try-anything entertainer, so this seemingly unlikely country-jazz summit with trumpet sensation Louis Armstrong (and Louis' pianist wife Lil Hardin) doesn't come as a shock. As Armstrong's languidly hypnotic horn intuitively follows, Rodgers plays the bluesy, possibly sloshed raconteur – when the Memphis po-lice grab him by the arm, he insolently replies, "You'll find my name on the tail of my shirt/I'm a Tennessee hustler and I don't have to work." Thank goodness Armstrong's there to get him home. By Charles Aaron

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4. George Jones, ‘He Stopped Loving Her Today’ (1980)

"Nobody will buy that morbid son of a bitch," George Jones told producer Billy Sherrill as he left the studio. Instead, "He Stopped Loving Her Today" was his first Number One in six years. If there's a bottom under the bottom, where humor mixes openly with despair, Jones knows it. By 1980 he was so lost he'd started speaking in split personalities, one of them Jones, another called the Old Man and a third called Dee-Doodle the Duck. It took him 18 months to finish "He Stopped Loving Her Today" on account of his speech being so slurred. The song's protagonist swore he'd love her 'til the day he died, Jones tells us, with Sherrill's string section rising behind him like some horror-movie hand shooting out of its grave. Then one day, he dies. Jones hated the song – he thought it was miserable and overly dramatic. It was. But country music often depends on the kind of hyperbole that real life can't bear. By Mike Powell

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3. Hank Williams, ‘I’m So Lonesome I Could Cry’ (1949)

No matter how one first encounters this song – Bob Dylan in Don't Look Back, Sandra Bernhard in her one-woman-show Without You I'm Nothing, Johnny Cash duetting with Nick Cave, even Pittsburgh Steelers QB Terry Bradshaw plodding through a 1976 effort – its wrenchingly poetic majesty remains undiminished. But the original stands as one of pop music's most masterfully controlled wails of emotion. Williams bemoans his failing marriage to wife Audrey, unveiling a series of deathly images (a whippoorwill too blue to fly, the moon hiding behind the clouds, a falling star silently lighting up a purple sky), which seesaw on the melody, until the singer concludes that he's "lost the will the live." Less than four years later, Williams was found dead in his Cadillac on New Year's Day. By Charles Aaron