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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.