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50. Steve Earle, ‘Guitar Town’ (1986)

Fueled by drugs, booze and a nasty divorce from his third wife, Steve Earle delivered this road anthem with a croon and a bark, snarling his way through lines about speed traps and truck stops with the authority of a rock & roll rebel who, at 31 years old, had already seen (and snorted) it all. Years of hard living eventually took their toll on Earle, who released three follow-ups to Guitar Town before spending the first half of the ’90s in a heroin-addled haze. By the time he cleaned up his act in 1995, the alt-country movement was in full swing and Earle joined a new generation of musicians – many of whom had strummed along to a Guitar Town cassette – in the effort to tear down the boundaries between country and rock.

49. The Louvin Brothers, ‘The Christian Life’ (1959)

A highlight of the Louvins’ second gospel album, 1959’s Satan Is Real, “The Christian Life” adds a homespun fire-and-brimstone attitude to the sort of Depression-era country harmonizing picked up from earlier sibling acts like the Delmore Brothers: “My buddies shun me since I turned to Jesus / But I still love them, they burden my heart,” Charlie and Ira sing in close harmony over a waltz rhythm. Almost a decade later, the Byrds went on to cover “The Christian Life” on their 1968 country-rock masterpiece Sweetheart of the Rodeo, with Roger McGuinn’s voice dubbed over Gram Parsons’ original lead vocal.

48. Willie Nelson, ‘Blue Eyes Crying in the Rain’ (1975)

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 marvels 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.

47. Bobbie Gentry, ‘Ode to Billie Joe’ (1967)

Innuendo has always played a role in folk and country music. But few songs piqued the pop crossover crowd’s curiosity more than Mississippi-born, Los Angeles-schooled Bobbie Gentry’s 1967 debut, in which an adolescent narrator and her family sit around the dinner table passing biscuits and gossiping about Billie Joe McAllister’s descent from the Tallahatchie Bridge. McAllister threw something else off it a day earlier and Gentry never reveals what it was. “The song is sort of a study in unconscious cruelty,” she once said of the family’s nonchalant attitude to the suicide. Released as the B-side to “Mississippi Delta,” “Ode” is a sultry country blues that drifts downstream on Gentry’s ominous acoustic guitar. Arranger Jimmie Haskell added dramatic strings, and three minutes were edited from her seven-minute original. Saxophonist Lou Donaldson’s funky 1967 instrumental version was sampled on dozens of hip-hop songs.

46. Roy Acuff, ‘Wabash Cannonball’ (1936)

Complete with choo-choo sound effects and the harmonica solo of some long-imagined cowboy, Acuff’s version of “Wabash Cannonball” was an early instance of country culture rising to meet the needs of city entertainment – the band even changed their name to the Smoky Mountain Boys once they made the Grand Ole Opry, presumably to retain that rural flavor. No surprise that he soon got into publishing and later ran for office – his moves always did seem a little strategic. But these are milestones, too; moments of friction in the development of a style as it took shape within the listening public at large.

45. Lefty Frizzell, ‘Long Black Veil’ (1959)

This 1959 saga of sacrifice is arguably the most persuasive primer on the pitfalls of infidelity. The hero of Frizell’s saga was wrongly executed for murder; he declined to give an alibi because was spending time “in the arms” of his best friend’s wife, a lethal indiscretion he takes to the grave. Since covered by Joan Baez, the Band, Johnny Cash, Bruce Springsteen and plenty of others, “The Long Black Veil” has become a country-folk standard, a grim, haunting evocation of forbidden love and all its consequences.

44. George Jones, ‘The Grand Tour’ (1974)

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 Jones’s 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’s 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’s 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.

43. Buck Owens and the Buckaroos, ‘Act Naturally’ (1963)

According to Owens’ autobiography, Buck ‘Em!, songwriter Johnny Russell stumbled into “Act Naturally” when a last minute Los Angeles recording session forced him to break a date with his Fresno girlfriend. When she asked what he would be doing, Russell gave her the line that would eventually open the song: “They’re gonna put me in the movies, and they’re gonna make a big star out of me.” Two years and several rejections later, Owens heard Russell’s demo and decided to record “Act Naturally” as part of the first sessions that brought his full road band, the Buckaroos, into the studio. Here, the group sounded tight and alive, the promise of that first line making the second – “We’ll make a film about a man that’s sad and lonely, and all I gotta do is act naturally” – all the more cutting. A Beatles cover helped a younger generation discover his music but Owens recalls a flight during which his neighbor explained to him how she loved the Beatles but hated country music. “As hard as I tried,” he said, “I couldn’t convince her that ‘Act Naturally’ was a country song.”

42. Loretta Lynn, ‘Coal Miner’s Daughter’ (1970)

This autobiographical reminiscence was a gear-shift for Lynn, who’d made her name by feistily fending off hordes of honky-tonk homewreckers 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.

41. Townes Van Zandt, ‘Pancho and Lefty’ (1972)

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 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 charts in 1983.