See 100-91 here

90. Ray Wylie Hubbard, ‘Redneck Mother’ (1975)

This second-tier Texas outlaw still writes, performs and records, but he dreamed up his only classic tune (recorded most famously by Jerry Jeff Walker, though Nineties alt-rockers Cracker do a killer version), early in his career, while kicking around in New Mexico. “Redneck Mother” flips a popular slogan among revolutionaries (as in, “Up against the wall…”) and flips the bird to country’s mother-worship. Never mind what Merle said – mama didn’t try hard enough, Hubbard suggests. If she had, maybe there wouldn’t be so many good-for-nothing drunks out there “kickin’ hippies’ asses and raisin’ hell.”

89. Gary Stewart, ‘She’s Actin’ Single, I’m Drinkin’ Doubles’ (1975)

 

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-affiliated gospel quartet the Jordanaires. An unreconstructed Southern rocker when he wanted to be, 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.”

88. Jerry Jeff Walker, ‘Desperados Waiting for a Train’ (1973)

Even back in 1970, Austin was getting weird, and Jerry Jeff Walker, a New York transplant backed by a band called the Lost Gonzos, was leading the transition. On his 1973 live-in-Luckenbach ¡Viva Terlingua! LP, he became the first to record “Desperados Waiting for a Train,” a track that another Austin transplant, Guy Clark, wrote while working at a dobro factory in California. Moonlighting as a songwriter, he came up with the title phrase and built around it the story of a grandfather figure to whom he had once been close. “He ended up in west Texas working for Gulf Oil,” recalled Clark. “To me, as a kid, he was a real desperado, the real deal. You can’t make this shit up.”

87. Lyle Lovett, ‘If I Had a Boat’ (1988)

In the mid-Eighties Lyle Lovett emerged on the bookish, folkie fringe of a new traditionalism that reacted against the pop leaning of the Urban Cowboy era. Consisting of little more than guitars – a finger-picked acoustic and a welling slide – “If I Had a Boat” is nothing to ride a mechanical bull too. And the abstract lyrics, which imagined Roy Rogers as confirmed bachelor and Tonto losing patience with the Lone Ranger, demanded concentration. Absurdist and meditative as it is, “If I Had a Boat” arose from a true story. Lovett claims he once tried to ride a pony across a pond. He wished he’d had a boat.

86. Donna Fargo, ‘The Happiest Girl in the Whole U.S.A.’ (1972)

Triumphant, hopeful and as corny as Kansas in August, North Carolina native Donna Fargo took this self-composed paean to young newlywed bliss to the top of the country charts. There’s no tortured dark-end-of-the-street sentiments for Fargo, who seems to mean every last “skippidy do da.” All that honky-tonk ne’er-do-well stuff about drinkin’ and cheatin’ and carryin’ on? That’s for middle age. For the two-and-a-half minutes that this lovers’ anthem lasts, it can wait.

85. O.B. McClinton, ‘Don’t Let the Green Grass Fool You’ (1972)

After failed attempts at R&B, country pastures were far greener for Osbie Burnett McClinton. Once the Mississippi native became the “Chocolate Cowboy” in the early Seventies, he rolled out a string of charting country hits featuring his rich baritone voice, able backup singers and a wry sense of humor. (“The Other One” corrected anyone mistaking him for Charley Pride.) McClinton’s biggest song, off 1972’s Obie From Senatobie (via Stax subsidiary Enterprise) was a twangier remake of R&B hit “Don’t Let the Green Grass Fool You,” which notched Number 37 on the country charts. Originally an early Wilson Pickett single, the perspective of an about-to-be-jilted lover trying to spark that old flame resonates in any genre.

84. Neko Case, ‘People Got a Lotta Nerve’ (2009)

Who cares that the song’s two protagonists – a killer whale and an elephant – were two unusual subjects for a country song? “I realized that it’s OK to admit that no matter who your characters are, you’re writing about yourself,” Neko Case told the New York Times. The first single from 2009’s Middle Cyclone, “People Got a Lotta Nerve” sent a stern warning to anyone foolish enough to tie the singer down. “I’m a man-, man-, maneater,” went the chorus, delivered with such poppy playfulness that it was easy to gloss over the song’s sinister undertow.

83. Bobby Bare, ‘Streets of Baltimore’ (1966)

This tragic tale of a man who gave up his entire life to make his woman happy in Baltimore (and who gets subsequently dumped there) was originally recorded by Bobby Bare, a singer most famous for working with a young Kris Kristofferson. But, as Bare told Rolling Stone in 1980, “Most of my hits would have been hits for anybody, I just got to ’em first.” So it was with “Streets of Baltimore,” penned by Tompall & the Glaser Brothers, who wanted to release the single themselves in September of 1966. Unfortunately for them, Bare got to it first (in June) and scored a hit, reaching the Number Seven spot on the country charts. The joke ended up being on Bare, though: For many, Gram Parsons’ 1973 version is widely considered the song’s most essential incarnation.

82. Reba McEntire, ‘Fancy’ (1991)

Written and recorded for Bobbie Gentry’s 1969 album of the same name, “Fancy” tells a rags-to-riches tale of a young girl whose mother sends her into prostitution. McEntire had wanted to record the song for years, but producer Jimmy Bowen argued against it – not because of the subject matter, but because he felt too many people associated the song with its original performer. When McEntire turned to Tony Brown for her 1990 album, Rumor Has It, the pair gave the song a striking loud-quiet-loud arrangement that helped introduce it to a new generation.

81. Gary Allan, ‘Songs About Rain’ (2003)

The second single from Allan’s See If I Care tells of a downtrodden masochist who’s wasting a perfectly good night driving in circles, listening to a perverse radio station that for some reason keeps playing songs – “Rainy Night In Georgia,” “Kentucky Rain,” “Here Comes That Rainy Day Feeling Again,” “Blue Eyes Crying in the Rain” – that all tell of stormy weather. But where the heartbroken man wallows in these tracks, Allan is busy placing his own in their lineage, successfully conjuring a country classic that’s as heartbreaking as the sum of its references. Co-writer Liz Rose, who has since helped pen a handful of hits by Taylor Swift, would later recall how “Songs About Rain” changed her career: “It wasn’t until I had the Gary Allan single that I could really say I was a songwriter.”