Rolling Stone’s 100 Greatest Country Songs of All Time — 40-31

Click here to see 100-91, 90-81, 80-71, 70-61, 60-51, 50-41

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.

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.

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.

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.

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.

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.

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.”

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.

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.

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.

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Rolling Stone’s 100 Greatest Country Songs of All Time — 70-61

Click here to see 100-91, 90-81, 80-71 

In the two decades Lee Ann Womack has been making music, she’s never made a splash like the one she made with this 2000 song. It charted at Number One on both the country and adult contemporary charts, won “Song of the Year” at the CMAs, ACMs, ASCAP awards and took home a Grammy for “Best Country Song.” Plus, between the years of 2000 and 2007, you couldn’t throw a rock at a high school graduation without hitting it. But according to the song’s co-writer Tia Sillers, it was actually less about how the children are our future and more about her rough divorce. Still inspirational, just more depressing.

Country music’s most parodied anthem (see Homer and Jethro paean to a doomed sow, “B-A-C-O-N & E-G-G-S”) began, unpromisingly, as “I-L-O-V-E-Y-O-U, Do I have to Spell It Out for You?” Songwriter Bobby Braddock found a juicier subject and song-plugger Carly Putman suggested a sadder melody. Producer Billy Sherrill brought the finished product to Tammy Wynette, whose achingly sincere limning of a mother spelling out the “hurtin’ words” in front of her four-year-old made the song her third Number One and the title track of her first gold album. “I hated myself for not writing that song,” the five-time divorcée later said. “It fit my life completely.”

When John Prine wrote “Angel” he’d been working as a mailman in the suburbs of Chicago, sketching out ideas as he made the rounds, playing open mics on weekends. At the time, country was cross-pollinating with the distinctly un-country sounds of pop and soft-rock, but Prine presented himself as something more stripped down: A regular guy with a plain voice playing simple music, no shoulder pads necessary. But it was his ear for detail – the flies buzzing around the sink, the rodeo poster that sends a woman on a daydream that she knows will never get fulfilled – that made his songs quietly complicated. Country music rendered with the sharpened eye of an author.

 

Recorded in 1972 but released in 1975, Lynn’s ode to reproductive rights turned out to be a difficult pill for many country stations to swallow – one of nine Lynn songs banned during her career. Written by Lorene Allen, Don McHan and T. D. Bayless, “The Pill” uses a chicken-coop metaphor (“I’m tearin’ down your brooder house”) to warn a straying cock that his hen may start exchanging her maternity-wear “garbage” for clothes that “won’t take up so much yardage.” Lynn, who birthed four babies by age 20, employs her throaty chuckle-growls to even the scales over funky chicken-scratch guitars. “They didn’t have none of them pills when I was younger,” Lynn wrote in Coal Miner’s Daughter, “or I would have been swallowing ’em like popcorn.”

When Cash recorded “Seven Year Ache” at age 25, it was with the soulful, seen-it-all purr of someone who’d endured the game for decades. And she had: Growing up with dad Johnny’s drug addiction, touring absences, divorce from her mom Vivian and second marriage to June Carter which forced her dual Tennessee/California identity; not to mention cultivating her own career, sustaining her first marriage to hotshot singer-songwriter Rodney Crowell and having their first child. Yet the mood on this career-defining Number One country hit – which chronicled a man’s wanderlust and apparently traced to a spat with Crowell (who produced the song!) – was an almost breezy reasonableness, as if the singer almost pitied the poor schnook. The melodic tick-tock was “Mellow Mafia” with a twangy moan, and Rosanne’s tart aphorisms were some of the genre’s most poetic.

Not to be confused with Jimmy Patton’s 1959 rockabilly track “Okie’s in the Pokie,” this megahit kicked Merle Haggard into the top tier of country performers. A Bakersfield-born son of Okie farmers, Haggard co-wrote this condemnation of pot smokers, sandal-wearers and draft-card burners on his tour bus with Strangers drummer Roy Edward Burris. Both parody (“pitching woo”? “Manly footwear”?) and counter-counterculture anthem – Hag once said its 24 lines contain “about 18 different messages” – “Okie” remains an undeniable a manifesto of ethnic pride.Haggard followed his relatively mellow Los Angeles studio original with a more truculent live version, then doubled down in January of the following year with his borderline-jingoist “The Fightin’ Side of Me.” Yet as he told a journalist decades later, “I didn’t intend for ‘Okie’ to be taken as strongly from my lips as it was.”

Recorded as a single in 1961 and included on Patsy Cline Showcase that same year, this track has became a country ballad standard – but it almost wasn’t. Producer Owen Bradley initially envisioned the track recorded by baritone Roy Drusky. According to Ellis Nassour’s biography Honky Tonk Angel: The Intimate Story of Patsy Cline, Cline was standing in the hallway when she overheard Drusky turn it down because it wasn’t manly enough. It ended up being his loss: Bradley agreed to let Cline take it over and she allegedly sang it so tenderly during sessions that it caused every man in the studio to cry. It became one of the first of several pop/country crossovers for Cline and charted for over six months.

A Top Five country hit in 1965, George Jones knew the ironic, upbeat number would be a hit the minute he heard it: “‘The Race Is On’ was pitched to me,” he later told Billboard, “and I only heard the first verse, [sings] ‘I feel tears welling up cold and deep inside like my heart’s sprung a big leak,’ and I said, ‘I’ll take it.'” Eight years later, the song took on new meaning when it became the first to be broadcast by New York’s WHN, the crossover-friendly radio station that would set audience records and define the sound of pop country in the late-Seventies.

Obviously, the blackface aspect of Emmett Miller’s act will forever shadow his legacy, but covers by everyone from Little Richard to Etta James to Ryan Adams to LeAnn Rimes are keeping “Lovesick” alive. Hank Williams didn’t learn everything he knew from Miller, but the sweet-singing 1920s minstrel performer did play a significant role inspiring country music’s founding father. A couple decades before “Lovesick Blues” became Williams’ first number one hit in 1949, Miller and his melancholy yodel were in love with a beautiful gal too. Miller’s version comes with a spoken intro in which he explains that he’s got “every known indication of being in that condition” before dappling the show tune, from the 1922 Tin Pan Alley musical Oh, Ernest, with some octave vaulting. For another take on Miller, hear David Lee Roth covering “Big Bad Bill (Is Sweet William Now)” on Van Halen’s Diver Down.

After periods emulating both smooth Eddy Arnold and honky-tonkin’ Hank Williams (whose Drifting Cowboys band he led after Hank’s death), Ray Price (a.k.a. “the Cherokee Cowboy”) returned to his Texas roots with this 1956 megahit that spent 20 weeks at the top of Billboard’s country chart. Co-writer Ralph Mooney penned the tune after his wife left him due to his drinking, and its lyrics suggest deep emotional delirium and paranoia. The music, however, reflected Price’s new shuffle style, with single-string fiddle, pedal steel guitar, and doubled acoustic and electric basses. Six months after Price’s release, Jerry Lee Lewis’s first Sun Records side was a more blatantly delirious rock cover that turned many heads.