On Jan. 1, 1997, the romance of tragedy that possessed Townes Van Zandt, both in song and in being, retreated in its wrenching final act. Having lived multiple lives worth of suffering, making travel companions out of addiction, penury and destitution, the perennially hurting folk bard left the world at the age of 52.

It was practically a self-fulfilling prophecy. "He told me three or four times in the last three or four years that he’d live to be 52,” his childhood friend Steve Wiener told Texas Monthly a year later. It was the same age Van Zandt's father had died of a heart attack in 1966.

Unlike the enchanting sorrow that colored the scenes in his illustrative verse, however, the sight of his passing would be an unsightly and disturbing one. After spending the week of Christmas immobile due to an untreated femoral neck fracture from collapsing at his home, Townes attempted to return to the studio while in a wheelchair, but the sessions were truncated by excessive intoxication and manic outbursts. Over a week went by before he’d consented to visit a hospital, and even then, he spurned detox and checked himself out prematurely. He fought dreadful withdrawal convulsions with a vodka flask while Jeanene, his wife, drove him back to their Smyrna, Tenn. home. It was there his youngest son, Will, is purported to have noticed he stopped breathing.

Van Zandt's death wasn't a shock to anyone familiar with how he lived his life. But shock isn’t a prerequisite for tragedy. And the tortured fabric that stitches together the lore of Townes Van Zandt wraps the songwriter’s proud simplicity in cult iconography, emotional complexity and enigma. This is why, say, the fact that he died 44 years to the day of his hero, Hank Williams, Sr., is as integral to the Townes Van Zandt id as is his 1972 masterwork The Late Great Townes Van Zandt or 1977’s endlessly mesmerizing Live at the Old Quarter, Houston, Texas.

Due to the peculiarity of timing, around the time of his death, he’d been enjoying a curious, albeit modest, spike in popularity driven by a new generation of alternative musicians attracted to the “outsider” status of unfairly shunned songwriting stalwarts unrecognized in their time. At the time, however, aside from a brief supporting stint opening up for indie alt-country darlings the Cowboy Junkies, Van Zandt had been largely idle, releasing mostly albums composed of live recordings from his creative heyday, which eventually compelled Sonic Youth drummer Steve Shelley to invite him to record for frontman Thurston Moore’s Geffen imprint Ecstatic Peace. The sessions were ill-fated, spiraling almost immediately into the disaster recounted above.

Still, it couldn’t be said that Townes’ passing was commercially self-sabotaging. As his protégé Steve Earle would tell the New York Times years later, “When somebody’s as good as Townes Van Zandt and more people don’t know about it, it’s Townes’ fault. For whatever reasons, he shot himself in the foot every damn chance he got.” Van Zandt conscripted himself to curiosity and whim and treated comfort and stability with contempt. Career and financial interests weren’t to get in the way of Van Zandt’s wandering spirit.

Watch Townes Van Zandt Sing "If I Needed You"

It was this spirit, after all, that led him to play guitar in the first place. Coming from a lineage of gentry Old West ancestry, Townes’ affluent upbringing initially nudged him in the direction of law school. Studious and athletically involved, anecdotes of his schooling indicate a future occupying the traditional wing of the upper-crust. But his hypnotic musical epiphany was sparked at exactly the same moment as so many other budding, young idealists who happened to tune in to the Ed Sullivan Show on Sept. 9, 1956 and watch Elvis Presley change the world on live television. But he was never pressured to bend toward the lofty social status affixed to his last name. On the contrary, it was his father who finally urged him to compose original material after a handful of stints covering the likes of Lightnin’ Hopkins and Bob Dylan.

And although the amount of albums sold throughout the course of his career was negligible at best, his intimate brand of chilling folk dirges would succeed in reversing the idolatry he’d had for his early heroes. Dylan, for example, cast a handful of unfruitful invitations to collaborate, eventually tracking him down at his motorhome in Austin, Texas demanding to be serenaded.

Contrary to popular belief, though, Townes didn’t actually die penniless. While he remained locked out of the mainstream (or, if you like, the mainstream remained locked out of Townes Van Zandt), the undeniable allurement of some works inevitably fought through, thanks to the homage of his more established admirers. Emmylou Harris and Don Williams drove their version of “If I Needed You” to number three on the Billboard Country Singles chart in 1981, and Willie Nelson and Merle Haggard topped it with his “Pancho & Lefty” two years later. The royalties he accrued from such homages neared the lower end of six figures—a reasonably comfortable mint, but Townes treated money like a leper. It was the next opportunity to record or perform that Townes recognized as compensation.

For all the physical, the mental atrophy, the disease of addiction, the condemnation of heartache, Townes Van Zandt was always nevertheless liberated by his ardent, though not always painless, freely willed lifework.

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