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70. Lee Ann Womack, ‘I Hope You Dance’ (2000)

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.

69. Tammy Wynette, ‘D-I-V-O-R-C-E’ (1968)

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.”

68. John Prine, ‘Angel from Montgomery’ (1971)

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.

 

67. Loretta Lynn, ‘The Pill’ (1975)

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.”

66. Rosanne Cash, ‘Seven Year Ache’ (1981)

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.

65. Merle Haggard, ‘Okie from Muskogee’ (1969)

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.”

64. Patsy Cline, ‘I Fall to Pieces’ (1961)

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.

63. George Jones, ‘The Race Is On’ (1964)

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.

62. Emmett Miller, ‘Lovesick Blues’ (1928)

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.

61. Ray Price, ‘Crazy Arms’ (1956)

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.