Townes Van Zandt, the elegant Texas troubadour who authored some of the finest songs ever written over the course of his 52 troubled years, was always quick to make it known that he was very much in on the cruel joke of his destiny. During a checkered, if frequently brilliant, recording career — often derailed by label concerns, production difficulties and Townes’ own recalcitrance — he produced a handful of outstanding albums possessing gallows humor titles like The Late Great Townes Van Zandt. Johnny Cash once famously bragged in song about shooting a man in Reno just to watch him die. Townes seemed committed to a similar experiment on his own physical being, drinking with such masochistic abandon and candid reportage that he made himself a veritable art project of personal desiccation — he would carefully record the minutes as all of us watched him die a Kafkan death. As inarguably exceptional as the body of work that Van Zandt left behind, it can feel ferociously dedicated to the depths of human despair, to the point of inaccessibility. Even a devoted miserablist like Lou Reed will occasionally allow that, “Anyone who ever had a heart/ wouldn’t turn around and break it.” Townes Van Zandt was the exception to the rule: He had a heart and smashed it into a million wretched slivers.

It is interesting to consider Townes’ trajectory as compared with his rough contemporary Gram Parsons — similarly a Southern child of privilege, gifted with extraordinary ability and cursed with a taste for excess. Both Parsons and Van Zandt shared a love for the great pioneers of early country and ’50s honky-tonk, while never fitting in with the more conservative tendencies of Nashville. Both rendered remarkable takes on the tradition, which were bound to be ignored by a plurality of rock and country audiences alike. But in other ways they were as different as they were similar. Parsons’ work was sweeping and ebullient, panoramic in its capacity to convey effervescent joy, crushing tragedy and heart-rending nostalgia. By comparison, to borrow a phrase, Van Zandt’s songs ran the emotional gamut from A to B. Even at its most irreverent, his vision was one of a capriciously nasty existence characterized by endless compromise and ceaseless yearning — the Albert Camus to Parsons’ Marcel Proust. That is not to value the work of one titan over the other, but rather to illustrate the iron-skinned dissolution that rendered Van Zandt’s work so difficult and indispensable.

That phrase — “Now you wear your skin like iron” — figures in Van Zandt’s most famous song and only bona fide chart success “Pancho And Lefty,” first released in 1972 and only a hit after a spit polished version rendered by Willie Nelson and Merle Haggard bulled its way to the top of the Country charts eleven years later. Ostensibly an Old West yarn concerning two desert bandits with a brotherly bond fractured by betrayal, it is in the spirit of Robert Altman’s great McCabe And Mrs. Miller — a demolition of frontier nostalgia that recasts the mythos of Western movie heroism as feckless, farcical and endlessly futile. As Lefty turns on his friend, leading to Pancho’s demise and the still worse, guilt stricken living death of Lefty, Van Zandt can’t help but twist the knife one turn further: “All the Federales say/ they could have had them any day.” These heroic jokers weren’t even all that good as outlaws.

“Pancho And Lefty” was, of course, also a thinly veiled metaphor for the life Van Zandt had chosen as a traveling musician — all the seeming romance and nobility gradually made null and senseless by dint of deprivation and drink, industry myopia and increasing audience indifference. As his career sputtered, Van Zandt’s legend amongst fellow songwriters grew exponentially — his close rapport with the great Guy Clark and mentorship of Steve Earle was part of the early story -but soon his talents were emphatically acknowledged by the heaviest of heavyweights — Bob Dylan, Willie Nelson, Merle Haggard and others. All of that and two bucks would have gotten him bus fare. Being an obscure figure admired by those far more influential and famous must have been a weird purgatory. Townes treated it as such.

In the final analysis we are left with a difficult figure — a writer of transcendent beauty and skill who leaves us both enriched and depleted in complicated ways. To spend time with the music of Townes Van Zandt is to engage with our darkest suspicions about our own time on this earth, with the faintest hint of silver lining. Unfailingly, he told the truth of his life. That was okay enough, but the scary part is wondering: was he telling the real truth of our lives as well?

Anyway, here’s 10 of his best tunes.

10. “Waitin’ Around To Die” (from For The Sake Of The Song, 1968)

The carefully finger picked, minor key lament “Waitin’ ‘Round To Die” is a typically efficient summation of Townes’ jet black worldview, replete with tales of romantic catastrophe, chemical excess, and perhaps most tellingly an unsparing recollection of domestic abuse more hurtfully candid then any this side of In The Aeroplane Over The Sea. There is no special drama or change in his voice while he relays the details: “One time, friends I had a Ma/ even had a Pa/ He beat her with a belt once cause she cried.” Van Zandt sings these words like a man reading the 6 o’clock news. In under three minutes of this harsh and strangely unsentimental masterpiece we come to understand why it is that the artist perceives his work as little more then a distraction from his inevitable demise.

9. “No Deal” (from High, Low And In Between, 1972)

The jocular folk ramble of “No Deal” finds Townes at his most light hearted, enumerating his reluctance to follow the supposed good intentions of medical doctors, auto salesmen and a would-be teenaged lover. Cheerfully debased and filled with great punchlines, it is the sort of rollicking shaggy dog tale that reminds us of the acid wit that was the mitigating flipside to Van Zandt’s crushing misery. When in the last verse he promises to choose hell over heaven, if there might be more whiskey in the former, it is an act of comedic, spiritual subversion worthy of our most treasured heretics. No deathbed confessions for Townes.

8. “Kathleen” (from Our Mother The Mounain, 1969)

The tense emotional apocalypse that is “Kathleen” begins with the typically Townes-ian sentiment: “It’s plain to see the sun won’t shine today/ But I ain’t in the mood for sun anyway,” and circumstances only darken further from there. As the narrator wrestles with encroaching insanity, waves of pain and panic, and a seemingly malevolent natural world of roaring oceans, prophetic swallows and a menacing firmament, the only apparent respite is death or the titular Kathleen. As the song progresses, so too does the suspicion that these things are one in the same. This is Townes at his most harrowing — a beautifully and genuinely frightening window into a fractious, tortured psyche.

7. “You Are Not Needed Now” (from High, Low And In Between, 1972)

Sounding for all the world like a lost outtake from The Band, the gospel-tinged, piano-driven “You Are Not Needed Now” belies its depressing title with a message of hope. “Lay down your head awhile, you are not needed now,” Townes beautifully and effortlessly soothes – it’s not your time to work, it’s not your time to suffer, it’s not your time to die. It is the rare Townes song that could be genuinely interpreted as optimistic – and it’s a cautiously optimistic beauty.

6. “Snake Mountain Blues” (from Our Mother The Mounain, 1969)

Just when you thought that Mick Jagger couldn’t be any more transgressive with “Some Girls,” here comes Townes, almost ten years earlier with sentiments like “Love of a blackskin woman, she won’t do you no wrong/ Yellow headed woman brings nothing but pain.” But while Mick and the Stones’ problems seem to start and end with their women’s material and … other appetites, Townes’ beguiling, dobro-assisted Tex-Mex shuffle seems steeped in more spiritual and existential concerns.

5. “Nothin'” (from Delta Momma Blues, 1971)

Nasty, brutish and short, the spare, finger-picked, cruel-to-be-cruel kiss off “Nothin'” is as immediate and powerful as a cannonball to the chest. What it lacks in charity it makes up for in its brevity, and it is devastating from its opening: “Hey mama, when you leave, Don’t leave a thing behind/ I don’t want nothin'” to its final sentiments “Sorrow and solitude, these are the precious things/ And the only words that are worth remembering.”

4. “Poncho & Lefty” (from High, Low And In Between, 1972)

Essentially the demolishing 3:40 antidote to every clichéd “I’m a cowboy/bad ass singer on the road” song ever written, this crushing tale of two outlaw friends driven apart through betrayal and deprivation is made all the more sad for the fecklessness with which the characters are portrayed. Over one of his loveliest ever melodies, Townes introduces us the two would-be mythic title characters — road warriors who live outside the law to maintain their freedom. A few well constructed verses later, Pancho is dead, Lefty is drinking himself to death in a Cleveland flop house, and the authorities, who simply paid one to turn on the other, were never all that concerned with them in the first place. Rarely has a song spelled out the true facts of America’s Old West mythology so plainly — it’s all such bullshit.

3. “No Place To Fall” (from Flyin’ Shoes, 1978)

The desperate lament “No Place To Fall” appears at first the libidinous appeal of a desperate man who is quick to admit that he “Ain’t much of a lover,” and is furthermore “here then I’m gone/ and I’m forever blue.” Or that is to say, not exactly a catch on Match.com. And yet as this gorgeous Neil Young-styled quasi waltz evolves, what is conveyed most is the sense of a deeply damaged soul in need of refuge — any sort of refuge — intellectual, spiritual, physical, or just a fucking place to crash.

2. “For The Sake Of The Song” (from For The Sake Of The Song, 1968)

The fetchingly lovely “For the Sake of The Song” originally appeared on Van Zandt’s debut album of the same name and was later recut for his self-titled third record. It is a thoughtful meditation on the nature of creativity, and perhaps a plea to the muse for a peace of mind that he would sadly never be afforded. “Why does she sing her sad songs for me?” the first line goes, the narrator seeming resigned to his place as a both receptacle for and manufacturer of vast oceans of melancholy. As the unhurried five minutes and twenty two seconds unfold, Van Zandt sings of shame and bondage, sorrow and pride, and most of all a welter of pain both unwanted and undeserved. The best he can figure by way of consolation is that it is all for the sake of the song. And so it would go for the remainder of his life and career.

1. “To Live Is To Fly” (from High, Low And In Between, 1972)

Van Zandt was known to his peers to possess a kind of effortless gift for songwriting — one which seemed to flow freely through him despite his persistent attentions to self-immolation. “To Live Is To Fly” is perhaps the greatest example of that effortlessness, a swift, breezy and beautifully bridgeless three minutes that floats by with seemingly impeccable grace and ease. It is also a song of wonderful philosophical and spiritual clarity — an instance of near Zen calm amidst the feverish storm of the singer’s life. Lyrics like “Everything is not enough/ and nothing’s too much to bear” come across here less as bitter and yearning, and rather like a sympathetic acknowledgment of our collective human predicament. In the end, Towne’s advises “It don’t pay to think too much on things you leave behind.” He was right of course- sage advice only too difficult for him, and all of us, to follow.

Listen to the Spotify playlist here.