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By Richard Skanse

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From blues and rock ’n’ roll to country and hip-hop, the Lone Star State has produced a size-appropriate share of bona fide legends over the decades, but it’s the acoustic guitar-wielding singer-songwriter that perhaps best exemplifies the independent spirit and outlaw mythos of Texas music at its best. By and large, the best Texas troubadours pay little heed to genre fences and the conventional rules of Songwriting 101. They set their own rules, break them at will, and dedicate their lives pursuing not so much the bridge between art and commerce as the golden mean between impeccable craftsmanship and true poetry.

  1. Townes Van Zandt “Songwriter’s songwriter” is a title that gets tossed around a lot, but when it’s bestowed by no less a giant than Kris Kristofferson upon a recipient as deserving as Townes Van Zandt, take it as gospel. Van Zandt, the scion of a Fort Worth oil family who battled manic-depression throughout his life and died at 52 on New Year’s Day 1997, wrote songs that could be both dazzlingly abstract and devastatingly direct, often in the same verse, and his melodies could be as beautiful as his blues were brutal (weigh the achingly lovely “To Live’s to Fly” against the harrowing “Waitin’ Round to Die.”) He was also a fleet flat picker in the tradition of his hero, Lightnin’ Hopkins, as evidenced on Van Zandt’s Live at the Old Quarter. Recorded in Houston in 1973, the double album is as essential as records in this genre get: 93 minutes of nothing but the poet, his guitar, and a sack of songs so bulletproof, he opens with “Pancho and Lefty.”
  1. Guy Clark A veritable Rock of Gibraltar to his mercurial compadre Townes Van Zandt’s rolling stone, the Monahans-born Guy Clark has called Nashville home for his entire recording career. Generations of younger writers, from Rodney Crowell to Hayes Carll, study his craft and strive for inclusion on his Dean’s List. By the time Clark released his flawless 1975 debut, Old No. 1, a fistful of his most enduring songs (including “Desperados Waiting for a Train” and “L.A. Freeway”) had already been canonized in Texas via covers by Jerry Jeff Walker. Decades later, a host of other esteemed troubadours (many on this list) did right by the master on the terrific This One’s For Him: A Tribute to Guy Clark. But as proven with every record he’s made up to 2013’s Grammy-winning My Favorite Picture of You, nobody sings a Clark song as definitively as Guy himself, his cigarette-toasted, West Texas drawl fitting every precision-tuned line “like a coat from the cold.”
  1. Willie Nelson Has any artist in country music ever had a more distinctive guitar sound than Willie? The Abbott-born songwriter had already penned most of his Nashville-era greatest hits (“Crazy,” “Night Life,” “Hello Walls,” etc.) by the time he finally acquired “Trigger” in 1969, but American music’s most iconic living artist and his beloved Martin N-20 classical have been inseparable ever since. Every record he’s made over the last four-and-a-half decades (and Willie makes a lot of records) has prominently featured his trademark tumbling leads and gypsy-jazz chording, every note plucked out of an instrument with a voice and battle-scarred face as singular as his own behind-the-beat phrasing. Willie, who turns 82 this April, is still as active as ever, and though he doesn’t write near as much as he records or tours anymore, 2013’s Band of Brothers—his first album in many years comprised mostly of originals—proves he can still knock out a stone-cold classic when he fancies. Just listen to “The Wall.”
  1. Kris Kristofferson Even if there were other Texas songwriters who could pad their resumes with “Rhodes Scholar, Army captain, chopper pilot, and silver-screen idol,” Brownsville’s Kris Kristofferson would still stand out from the crowd by merit of being the only one who also wrote “Me and Bobbie McGee,” “Sunday Mornin’ Coming Down,” “Help Me Make It Through the Night” and “For the Good Times.” Although his songs are best known through other voices (most notably Janis Joplin and Johnny Cash), Kristofferson’s writing alone was a game changer, serving notice to the mainstream and rock snobs alike that country music could be every bit as sophisticated and scary smart as Dylan at his best. And damn, was he suave! “I ain’t saying I beat the devil,” he growled on his 1970 debut, sounding like the most interesting man in the world, “but I drank all his beer for nothin’ … Then I stole his song.”
  1. Billy Joe Shaver Armed with an eighth-grade education and a right hand shorted two fingers in a saw accident, Billy Joe Shaver has written some of the finest hardscrabble country songs this side of Hank Williams. The Corsicana scrapper was an Outlaw’s outlaw from the git-go, with Waylon Jennings recording almost an entire album of his songs (1973’s Honky Tonk Heroes) the same year that Kris Kristofferson produced Shaver’s seminal debut, Old Five and Dimers Like Me. Shaver’s songbook from the ’70s is chock full of progressive country classics (“Black Rose,” “Georgia On a Fast Train”), but he recorded many of his best albums in the ’90s with MVP support from his guitar-hero son, Eddy: 1993’s Tramp On Your Street, featuring arguably his best song, “Live Forever,” is a masterpiece. Eddy’s death in 2000 and myriad other obstacles (both health- and legal-related) have knocked Shaver sideways numerous times over the last decade-plus, but 2014’s Long In the Tooth finds the “Old Chunk of Coal” still fit as the proverbial fiddle—and still plenty randy for a born-again Christian soldier.
  1. The Flatlanders: Butch Hancock, Joe Ely, and Jimmie Dale Gilmore We’re cheating here, given that all three of these guys deserve their own spot on this list (along with fellow Lubbock luminary Terry Allen, if only his weapon of choice were guitar rather than keyboards). But even though whip-smart raconteur Hancock (“If You Were a Bluebird”), roots-rocker Ely (“Letter to Laredo”) and cosmic honky-tonker Gilmore (“Dallas”) have all established storied solo careers, any time their stars and schedules align is cause for celebration. Fortunately that happens a lot more nowadays than it used to: After waiting 30 years to follow-up their 1972 debut with 2002’s Now Again, the three amigos have taken to touring and recording together fairly regularly over the last decade.
  1. Rodney Crowell From his salad days as a disciple of Guy Clark and Townes Van Zandt in the early ’70s through his stint playing rhythm guitar in Emmylou Harris’ formidable Hot Band, Rodney Crowell wrote a handful of songs that remain some of his most enduring crowd favorites, including “Till I Gain Control Again,” “Ain’t Living Long Like This,” and “Leaving Louisiana in the Broad Daylight.” But his best work was yet to come, most notably 1988’s edgy country blockbuster Diamonds & Dirt (which launched a record-setting five No. 1 chart hits) and his 2001 Americana masterpiece, The Houston Kid. Crowell’s continued in strong, prolific form ever since, continually raising his own bar both as a solo artist (see 2003’s splendid Fate’s Right Hand and 2014’s widely-acclaimed Tarpaper Sky) and as a collaborator (as on his Grammy-winning 2013 duo record with Harris, Old Yellow Moon.)
  1. Nanci Griffith Austin-reared folkie Nanci Griffith has long been a champion of other writers, from up-and-comers such as Lyle Lovett and Robert Earl Keen to heroes including the host of folk icons (Dylan, Prine, Van Zandt, etc.) she paid tribute to on her Grammy-winning 1993 set, Other Voices, Other Rooms. But her own compositions are just as strong, with poetic jewels like “Love at the Five and Dime,” “Gulf Coast Highway,” and “It’s a Hard Life Wherever You Go” cut with bittersweet nostalgia, palpable heartbreak and astute social awareness that rings as pure as her sweet Texas twang and strong, gorgeous melodies.
  1. Steve Earle Like Rodney Crowell, Texas ex-pat Steve Earle honed his craft at marathon song-pulls with Guy Clark and Townes Van Zandt in Nashville before finding a quick taste of mainstream country fame with his rollicking 1986 debut, Guitar Town, and even a flash of rock radio love via the hard-hitting title track of 1988’s Copperhead Road. But from the acoustic renewal of ’95’s Train a Comin’ to the rousing post-addiction surge of ’96’s I Feel Alright and onwards, he’s evolved into one of the most stridently political and adventurous artists in modern Americana music—a self-styled “Hardcore Troubadour” as comfortable playing bluegrass with Del McCoury as he is raging against the death penalty, fascism and other social ills with swagger (and maybe a borrowed riff or two) reminiscent of the Stones at their “Street Fighting Man” best.
  1. Robert Earl Keen Although best known for “The Road Goes On Forever,” Houston-born, Kerrville-based Robert Earl Keen hasn’t maintained his standing as one of the biggest live draws in Texas since the ’70s heyday of Jerry Jeff Walker on the strength of one rousing anthem alone. His catalog is stacked with three-decades’ worth of modern classics every discerning Americana music fan should know by heart, ranging from sing-along favorites including “Gringo Honeymoon” to such songs as “Corpus Christi Bay,” “Dreadful Selfish Crime” and “Wild Wind” that feel as cinematic in scope and narrative detail as Texas novelist Larry McMurtry’s The Last Picture Show. Keen is also a peerless bandleader and savvy, inventive interpreter, qualities brought to the fore on his first collection of all covers, 2015’s Happy Prisoner: The Bluegrass Sessions.