The 200 Greatest Country Songs of All Time

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 and 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 Chicks, even showing up on The Voice as the audition song for Gracia Harrison. —C.A.

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. —K.H.

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. 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. —M.P.

Featuring a typically great Ronnie Dunn vocal performance, “Neon Moon” was one of four Number One singles from Brand New Man, Brooks & Dunn’s debut album as a duo. Singer-guitarist Kix Brooks provides vocal support, while Dunn describes a scene of desolation and heartbreak that sounds strangely like an oasis. Despite the sense of loneliness and loss, Dunn keeps just enough light in his bummed-out lyrics. “I was taught, when I got into the co-writing thing in Nashville, to always leave just a ray of hope,” Dunn told CMT. “It’s got it. He’s OK as long as he’s sitting under that neon light.” Kacey Musgraves understood the magic of “Neon Moon” — she recut the tune with Brooks & Dunn for the collaborative 2019 album Reboot, turning it into a shimmering electro-pop number. —J.F.

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 George Jones’ 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’ 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’ 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. —R.G.

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 Presley-affiliated gospel quartet the Jordanaires. 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.” —R.G.

“We didn’t have much money for entertainment,” Loretta Lynn wrote in her 1976 autobiography, Coal Miner’s Daughter. “I never went out much because we couldn’t afford a babysitter. Besides, Doo [Oliver Vanetta Lynn, her husband of nearly 50 years] liked to go out with the boys and have a few beers.” Cue this prickly 1966 smash, her first Number One, co-written with sister Peggy Sue (“My bank account loves that song as much as I do”), a spritely rejection of whiskey-dick’d marital overtures. It touched off a feud via Jay Lee Webb’s cold-blooded 1967 answer record “I Come Home A Drinkin’ (To a Worn-Out Wife Like You),” but the best cover version is a 2010 rave-up from Gretchen Wilson. —R.H.

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 Townes 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 chart in 1983. —D.M.

“Even if [people] don’t agree with the girls-kissing-girls thing or even the drug reference,” Kacey 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. —M.P.

With a voice stirring together the low end of Johnny Cash and the high whine of Hank Williams, Garth Brooks was just beginning his historic superstar run. A few 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 bestselling 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. —R.F.

In the closest thing outlaw country has to an official mission statement, a black-clad and bearded Waylon Jennings confrontationally pushed back against the era of “rhinestone suits and new shiny cars.” Written on the back of an envelope on the way to the session with Sun Records veteran “Cowboy” Jack Clement, “Are You Sure Hank Done It This Way” is both a prickly barb setting Jennings apart from the Nashville status quo and a cry of freedom. Jennings, who would often wear a pair of Hank Williams’ boots given to him by Hank Jr., called the original country icon his “outlaw hero.” In his autobiography, Jennings wrote, “We wanted to be like him, romanticizing his faults, fantasizing ourselves lying in a hotel room sick and going out to sing, racked with pain, a wild man running loose even if it meant dying in a blue Cadillac on the way to greet the new year in Canton, Ohio.” —C.W.

Recorded with an all-star band that included Elvis Presley’s piano player, the Grand Ole 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. —A.L.

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.” —R.G.

“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 chart 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 among 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. —J.B.

A song so big it’s easy to forget Shania Twain was already a star when it sauntered onto the charts, “Man! I Feel Like a Woman” capped off a run that defined 1990s pop country and made Twain a global phenomenon. Perfectionist producer (and her then-husband) Mutt Lange arranged big drums, bigger guitars, and even bigger synthy horn blasts as Twain belts out a girl-power anthem that ended up conquering an era that was full of them. With a new hook seemingly every few measures and an outrageously catchy chorus, it may be the ultimate country karaoke song of all time. Let’s go, girls. —J. Gross

Not so much straight “country” as the blues seasoned with rural fiddle, “Sitting on Top of the 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 reissued their entire catalog through his Document label — presumably lured by that “real thing” feel in their gritty but obscure sound. —M.P.

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. —C.A.

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 marvel 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. —R.H.

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.” —C.A.

Country music rebel Johnny Cash was at his best when taking extreme measures: all-black clothing, performing for felons, and singing about unbridled love with flames to illustrate his point. Written by songwriter Merle Kilgore and June Carter (or Cash himself, according to less savory accounts about the lyrics’ meaning), the song was originally recorded as an acoustic folk tune called “(Love’s) Ring of Fire” by June’s sister, Anita Carter. When it didn’t net her a hit, Cash retooled the arrangement with mariachi horns, electric guitar, and his barreling voice — backed by Mother Maybelle and the Carter sisters. After its 1963 release, the Number One reign of “Fire” on the country chart lasted seven weeks. Kilgore, who later managed Hank Williams Jr., tried to place “Ring of Fire” in a Preparation H ad in 2004, but Cash’s surviving family wisely nixed the idea. The song lives on more reverently in the hands of rock bands like Eric Burdon and the Animals (who scored a Top 40 single in 1969) and SoCal rockabilly punks Social Distortion. —R.F.

Charlie Rich had been struggling to find a niche between his rocking, jazz-picker roots and the Music Row mainstream for two decades. Then “Behind Closed Doors” gave the so-called Silver Fox the biggest hit of his career. “The jocks had been complaining that [Rich] was too bluesy for country,” producer Billy Sherrill explained to Billboard in September 1974. “Others said he was too country for anything else. We just needed the right song.” To create that right song, Sherrill and Co. started with a riff that writer Kevin O’Dell had been humming for years, and then balanced traditional country flourishes with the dramatic orchestral instrumentation of an 11-piece string section. Rich won two Grammys and his only CMA Entertainer of the Year award. —M.R.M.

This domestic abuse revenge tale caused minor controversy when it was released, but songwriter Dennis Linde shrugged it off: “I thought I was writing a black comedy like Arsenic and Old Lace or The Trouble With Harry,” he told the Los Angeles Times. Long story short: He gives her a black eye, she poisons his black-eyed peas — but it’s ultimately a love song since she reunites with her high school BFF by song’s end. Chick Emily Robinson undercut the brouhaha with a little sarcasm, telling the media, “We’re not promoting murder, and we even say that in a disclaimer on our album. Besides, is there a gentler way to go than with black-eyed peas?” —N.M.

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’ film 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. —R.G.

“I thought that one was a home run the minute I heard it,” Kenny Rogers has said of the most famous story-song in country history. Don Schlitz wrote most of the gambling allegory in 1976 while walking home from a meeting on Music Row, but it took the songwriter six weeks to come up with the inconclusive final verse. Producer Larry Butler gave the song to both Johnny Cash and Rogers to record, but he placed his faith in the latter. “I got a funny feeling,” Butler told the singer, “that if you do this, you will become the Gambler.” Butler’s prophecy proved true, as the classic country narrative quickly became Rogers’ signature tune, earning him a Number One spot on the country chart, a Grammy, and a series of television movies, starring Rogers as the Gambler. —J.B.

On the frolicking “Mean,” Taylor Swift sounds like she has queen bees, bullies, I’m-a-let-you-finishers, and corrosively cruel music critics in her banjo machine-gun’s sights. From 2010’s Speak Now, the song was an eventual Number Two country hit — and Number 11 on the Billboard Hot 100 — partly because it captures the sting of “words like knives.” It’s real power lies in giving enough ammo to empower victims of bullying even worse than those Swift suffered (i.e., getting mixed reviews for a Grammys duet with Stevie Nicks). It’s the sound of a 19-year-old artist balancing her sound to pull in country fans while also opening the palace gates for the still-greater pop stardom that was just on her horizon. —R.F.

Charley Pride’s 1971 recording of Ben Peters’ “Kiss an Angel Good Mornin’” remains the definitive version of this a slightly naughty love song attempted by Conway Twitty, George Jones, and Alan Jackson. The piano-driven arrangement here is classic early-Seventies countrypolitan, propelling the singer’s only crossover Top 40 pop hit. Pride’s métier has always been an easygoing effortlessness, which perfectly suits this ode to the pleasures and virtues of “Drunk in Love”-style domesticity. —D.M.

Arkansas-bred Lefty Frizzell had a gentle drawl that made even his rowdiest songs go down sweet. His debut single — covered by George Jones, Merle Haggard, and Willie Nelson — taught an entire generation of country vocalists how to sing. The honky-tonker was immediate hit, selling a whopping 500,000 copies in two months. Frizzell was barely 22 when he co-wrote the song with A&R man Jim Beck, who first discovered the young singer in Texas. Frizzell came up with the idea for the lyrics when one of his friends tried to persuade the musician to go out with him one night. “He said, ‘Lefty, do you want to go?’ And I said, ‘Well if you got the money, I got the time,’” says Frizzell. “It dawned on me this would be a beautiful idea for a song.” —J.B.

Ernest Tubb started his career as a Jimmie Rodgers mimic but lost his yodel in 1939 when a doctor took out his tonsils. He soldiered on and became one of pop’s first great terrible singers, with a voice so wooden that even he made fun of it. But like basically every successful youth-oriented musician of the last century, he had the keen idea to quicken the pace and firm up the beat, making the song as much about the accompaniment as the lead. “Walking” was an early instance of country music’s fascination with the electric guitar, a rude instrument used in places of questionable morality. If anything, Tubb’s voice only helped foster the idea that he was authentic — a regular dude who made good on his shortcomings and sold millions. —M.P.

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 singer Buck Owens 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 back seat, 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 chart and eventually providing the Nashville establishment outsider with the first (and highest charting) crossover pop single of his career. —J.B.

A.P. Carter, patriarch of country music’s first family, took a rather severe Christian hymn dating back at least to 1907 (when the sheet music for “Will the Circle Be Unbroken” was first published), altered the title slightly, changed the lyrics substantially, and produced a stirring, stoic, nondenominational expression of collective sorrow in the face of death on a 78 rpm disc. It would become a harmony-powered, genre-transcending standard, at funerals and elsewhere, in gospel, folk, country, and country rock. Notable in the last style is the pioneering version by the Nitty Gritty Dirt Band on their all-star 1972 triple LP, Will the Circle Be Unbroken, featuring vocals by “Mother” Maybelle Carter herself. —W.H.

This autobiographical reminiscence was a gear-shift for Loretta Lynn, who’d made her name by feistily fending off hordes of honky-tonk home wreckers 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. —K.H.

Western swing pioneer Bob Wills wrote “Spanish Two-Step” in his early days of entertaining Mexican audiences, created the original “San Antonio Rose” at a 1938 session by playing its bridge backward, and added new lyrics two years later to score his first national hit. Uptight traditionalists have criticized innovative country stars for deviating from some imaginary idea of “real country” for just about as long as there have been country stars to criticize, and Wills was no exception, outraging the cranks when he played his signature tune at the Grand Ole Opry with drums and horns. —K.H.

The romantic story about “Wichita Lineman” is that Jimmy Webb wrote it after seeing a lonely guy working at the top of a telephone pole while driving through the voids of rural Oklahoma. The truth is that Webb’s last song for Glen Campbell, “By the Time I Get to Phoenix,” had been a hit, and Capitol Records had called to demand more. “I really sat down to write something that would please them mostly,” Webb confessed to the Dallas Observer in 2006. The sound — a haze of soapy violins and expansive chord changes — had more to do with the onset of soft rock than the rudiments of country, but the subject matter was a new spin on an old story. Country calls it individualism; Webb called it loneliness. —M.P.

There’s a great history in American music of answer songs that trump their targets — “This Land Is Your Land,” “Roll With Me, Henry,” “Sweet Home Alabama,” “Roxanne’s Revenge” — and this includes Kitty Wells’ riposte to Hank Thompson’s 1952 hit “The Wild Side of Life.” The original condemned an ex-fiancée (whom the singer appears to have stalked) as a common floozy. Wells’ revved-up reply (via songwriter Jay Miller, with husband Johnnie Wright on bass!) indicted unfaithful men for making their own empty beds, and scored the first Number One country hit for a solo female artist, inspiring generations to resist submissive stereotypes. As testament to Wells’ groundbreaking courage in recording the song, NBC Radio banned it, and the Grand Ole Opry forbade her from performing the song on its hallowed stage. —C.A.

George Strait’s finest recording is one of his very few singles to never reach Number One — an anomaly, really, considering he’s in elite double-digit territory with his mountain of chart toppers. But “Amarillo by Morning,” written by Terry Stafford and Paul Fraser, is not your everyday radio fare. There’s the contrasting sense of desolation and self-determination that course through the lyrics, which center on an aging cowboy who’s forfeited everything in his life to the lure of the rodeo. There’s Blake Mevis’ production, which incorporates a gorgeously lonesome fiddle lick right from the top and conveys a sense of rootless melancholy that’s at odds with the song’s surprisingly brisk tempo. And then there’s Strait, whose elegant croon is the epitome of pathos and realness, sounding just like someone who knows the feeling of having to fold his broken body into the driver’s seat and haul ass through the long Texas night to make it to the next gig. —J.F.

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 run the Grateful Dead, who performed it at Woodstock and on more than 300 subsequent occasions. —R.G.

A family-values tract with its share of contradictions (Tammy 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 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. —K.H.

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 Armstrong’s 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. —C.A.

This Cindy Walker- and Eddy Arnold-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. —R.F.

“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. —M.P.

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. Hank 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. —C.A.

Written for Billy Walker, this jukebox jackpot got to Patsy Cline through husband Charlie Dick, a Willie Nelson crony from Tootsie’s Orchid Lounge on Nashville’s Music Row. After hearing Nelson’s demo (an emulation of Floyd Tillman’s “I Gotta Have My Baby Back”), Dick immediately drove the songwriter home to wake up Cline. She initially judged Nelson’s tune too slow, too mannered, and unflattering, but nonetheless nailed her heart-stopping, self-interrogating vocal in a single. Floyd Cramer played the spare, walking-after-midnight piano riffs, and Elvis Presley’s Jordanaires served as Greek chorus. “Crazy” went on to become Cline’s signature tune, a hallmark of the Great American Songbook, and 1992 independent presidential candidate Ross Perot’s campaign anthem. —R.G.

The defining moment for country’s most iconic figure. What makes “I Walk the Line” a great song? Johnny Cash’s transcendent baritone (“A voice from the middle of the Earth,” recalled Bob Dylan), the Tennessee Two’s austere rhythms, the lyrics’ puppy-dog romanticism, and the goofy hums that telegraph the key changes. But what makes it a great country song? The fact that Cash wasn’t always walking said line. At least not in a secular sense: Written on the road (most likely in East Texas) and released in 1956 (Sun Records boss Sam Phillips insisted on picking up the tempo), the tune is largely a reassuring love letter to Vivian Liberto Cash, the singer’s first wife — but, given that the 2005 biopic named after the song chronicled Johnny’s subsequent eternal love affair with June Carter Cash … well, yeah. Robert Hilburn’s 2013 biography quotes Cash conceding that he was partly singing to God, too: “Sam never knew it, but ‘I Walk the Line’ was my first gospel hit.” —R.H.

“Jolene” is Dolly Parton’s pinnacle as a singer, songwriter, and storyteller: the ultimate country heartbreak song. And after 50 years, it’s more iconic than ever. “I was telling my own stories, speaking my own feelings,” Parton told Rolling Stone in 1975. “I’m a pretty bold person.” While the world was falling in love with her self-described “Backwoods Barbie” image, she was fighting to make her way as a woman in Nashville, writing tough-minded tales like “Coat of Many Colors” and “Down From Dover.” In “Jolene,” she begs another woman not to steal her man, hitting high-lonesome notes straight from the Great Smoky Mountains. It was a Number One country hit in 1973, yet it feels both ancient and uncannily modern. “Jolene” has inspired great interpretations by artists from Miley Cyrus to the White Stripes to Beyoncé. But it’s the song that sums up Dolly Parton at her realest and greatest. —R.S.