To really die you have to die three ways. Townes Van Zandt discovered this after overdosing on model airplane glue. He was declared DOA at the hospital where, to hear him tell it, he sat for an hour and a half while doctors debated just how dead he was. “There’s brain death, which I’ve suffered. There’s respiratory death, which I haven’t suffered yet. And there’s heart death, which I go through every two or three months,” he told filmmaker James Szalapski. “But I figure if you’re ever all three of those at once, that’s it. That’s the ballgame.”

Van Zandt died more than most because he lived more than most. He reasoned that to write great songs, he would have to experience everything that he could survive and a few things he couldn’t. As a freshman at the University of Colorado at Boulder, he tipped backward over the railing of a fourth-story balcony just to see how it felt to lose control. “I started leaning back really slow, and really paying attention,” he recalled to journalist William Hedgepeth. “I fell over backwards and landed four stories down flat on my back. I remember the impact and exactly what it felt like and all the people screaming.” This kind of thing makes for a good story but a turbulent life. Van Zandt kept his balance between chaos and calm for as long as he could, but he always knew which way he would fall.

Whatever fame Van Zandt achieved was very nearly accidental. He went along, in a limited way, with the machinations of the music industry, recording six remarkable albums in five years between 1968 and 1972. Almost despite himself, he was on the verge of a breakout success with his seventh record, to be called Seven Come Eleven. Recorded in the spring of 1974, it was meant to build on his considerable momentum and launch him onto the national stage. However, the album would not be released for nearly 20 years. By the time it hit shelves in 1993, now titled The Nashville Sessions, Van Zandt was a cult figure, a songwriter’s songwriter better known for other artists’ covers of his work. Rather than a career-defining album, Seven Come Eleven had become a footnote in a tragic story.

Van Zandt came from a reputable family. Townes Hall at the University of Texas is named after one side and Van Zandt County, outside of Dallas, after the other. His father was high up in the oil industry and his mother wanted Townes to be a lawyer or a politician or an oil man himself. Van Zandt mainly wanted to get drunk and hit the road. After the balcony stunt, Townes got a friend to forge a letter to the dean excusing him from the rest of the semester and hitchhiked to Oklahoma and back. Upon learning of this behavior, his parents flew up to Boulder, took him out of college, and put him in a psychiatric hospital in Galveston, where he received a combination of insulin coma therapy and electroshock therapy. At the time, this method was at the cutting edge for his diagnosis of “schizophrenic reaction.” A side effect of the three-month-long treatment was the erasure of his long-term memory. Afterward, he had to be reintroduced to his mother: She was the one with the long hair.

Townes tried to settle down for a while. In 1965, he married Fran Peterson and they moved into a nice apartment in Houston provided by his parents. He enrolled as a pre-law student at the university. But quickly enough, Van Zandt locked himself into a closet to write his first song, “Waitin’ Around to Die,” an ode to rambling, gambling, and crime that ends with a confession of love to codeine. It wasn’t the type of song that his new wife expected during their honeymoon phase. He started playing in local clubs and coffeehouses for $10 a night and was soon putting more effort into his music than his studies. In a last-ditch attempt at stability, Van Zandt tried to enlist in the military but failed the psychiatric evaluation. The doctor called Townes “a manic depressive that had made minimal adjustment to life” and advised him to “wander for a while and find himself.” Now under doctor’s orders, Van Zandt set off.

“There was one point when I realized, ‘Man, I could really do this,’ but it takes blowing everything off,” Van Zandt said. “It takes blowing your family off, money, security, happiness, friends. Blow it off. Get a guitar and go.” He told Fran to wait for him at home, to be a source of safety and sanity that he could return to between stretches on the road. Fran held down a job at Shell Oil and took care of their first child, J.T., while Townes spent weeks or months touring. Visits home became less frequent. “A couple of times that he came back to see J.T. or when he would just call me out of the blue, he would say ‘Sanity is further away,’” Fran remembers in Margaret Brown’s 2004 documentary Be Here to Love Me.

Van Zandt’s big break came from Mickey Newbury, a songwriter working for Nashville’s biggest music publisher, Acuff-Rose. Newbury had written songs for Elvis Presley, Ray Charles, and Joan Baez, among others, and had exactly the connections that Townes needed. Van Zandt had recorded a demo of “Tecumseh Valley,” a folk song about a miner’s daughter who turned to prostitution after the death of her father. Newbury’s production partner played him the tape and asked if they could do anything for this unknown singer. “Hell, I don’t know, but he sure deserves it,” Newbury said, and signed him to a management contract. Newbury introduced Townes to “Cowboy” Jack Clement, a Nashville producer of hits by Roy Orbison, Jerry Lee Lewis, and Johnny Cash, who promised to record and publish his first set of songs.

When it came to his career, Van Zandt was his own worst enemy. He didn’t care for contracts or royalties or the recording process itself—according to legend, he once offered his full publishing rights to the first person who could score him some drugs. A close second, though, was Kevin Eggers, a New York agent who was then scouting for talent for his new label, Poppy. He came recommended by a friend of Clement’s, Lamar Fike, who was a close confidant of Elvis. Townes’ camp sensed trouble early on. “I don’t have much good to say about him,” Cowboy Jack told biographer John Kruth, author of To Live’s to Fly. “I think he was bad news for Townes… worst thing that ever happened to him.” Newbury, too, said Van Zandt’s deal with Eggers was “the worst move he ever made in his life.” But Eggers was a fast talker and an inveterate self-promoter who wooed Van Zandt with his anti-establishment stance. Townes signed a contract with Poppy for his debut album, For the Sake of the Song, in 1968.

Clement didn’t know what to do with Van Zandt in the studio. Townes’ holy trinity comprised Hank Williams, Lightnin’ Hopkins, and Bob Dylan, but he didn’t exactly fit the mold of a country, blues, or folk artist. Cowboy Jack forced the trendy Nashville sound onto For the Sake of the Song, adding organ, harpsichord, and backing vocals onto Van Zandt’s sparse compositions. In Clement’s hands, the somber “Waitin’ Around to Die” became a spaghetti western track. Any mention of prostitution was stripped from “Tecumseh Valley” in consideration of the conservative country audience. This latter decision caused a rift between Clement and Eggers that would never fully be resolved. Clement similarly overworked Townes’ second album, Our Mother the Mountain, before Eggers looked elsewhere for a producer.

The problems with Eggers started immediately. Nobody knows where the money from Van Zandt’s first big contract went. “I’m not really sure what happened, but that check for 80,000 dollars got torn up or disappeared,” Fran later said. “We could barely pay the hospital bill when J.T. was born.” Townes’ attitude toward money didn’t help. He would give fistfuls of it to strangers, or gamble it away, or spend it on drugs and alcohol. Poppy released a handful of Van Zandt’s albums, but Eggers’ accounting was never transparent. Still, Van Zandt stayed loyal. He knew that he would always earn more from touring than from selling records and didn’t care enough about royalties to chase them down.

During this era, Van Zandt’s tours often traced a boomerang: starting in Colorado, moving south to Houston, and then east to Nashville and back. Houston was a problem because that’s where Townes could score heroin. Soon, his summers in Colorado turned into retreats from his addiction. In 1970, Townes and Fran divorced as his behavior grew more erratic. The next year, he moved in with a dealer in Pasadena, an industrial section of Houston, where he had unlimited access to his drug of choice. Van Zandt started to sell off all of his possessions, including his record collection, and to avoid friends and family.

Fran convinced Townes to visit J.T. in the fall of 1971. He didn’t show. Sensing that something was wrong, she waited by the phone all day. Finally, the call that she was dreading came: Van Zandt had overdosed. He was in the hospital, calling out her name. When Fran arrived, she was told that Townes had died again, twice this time, in the ambulance. His condition was still critical, but she kept him conscious by talking to him throughout the night.

To celebrate his most recent recovery from death, Van Zandt jokingly named his sixth record The Late Great Townes Van Zandt. Eggers claimed that he was responsible for the title, meant to poke fun at Townes’ dead career. Really, though, he was as successful as he had ever been. The Late Great sold steadily and featured two songs, “If I Needed You” and “Pancho and Lefty,” that would come to define his career. Van Zandt had survived, even prospered, and was eager to continue his lucky streak. He looked forward to his seventh album with anticipation. “The next one will be a hit. The next one is likely to be a hit,” he predicted.

He had reason to be confident in the songs on Seven Come Eleven. Townes often claimed that he was only a vessel for lyrics that really originated elsewhere. They would come to him in flashes or in dreams. This may have been true sometimes, but was more likely a bit of modesty mixed with mythmaking: the humble poet, divinely inspired. However he arrived at his songs, Van Zandt was always meticulous. “It seems a lot of people in Nashville write by the phrase, or by the line. As opposed to writing by the word,” he told journalist Paul Zollo for the 2003 book, Songwriters on Songwriting. “A lot of my best songs are where every single word is where it’s supposed to be.” He was influenced by Shakespeare and Dylan Thomas but cited Robert Frost as his most important touchstone. As in Frost’s best poems, Van Zandt’s lyrics are profound in their simplicity.

Townes’ friend and fellow outlaw songwriter Guy Clark has called Seven Come Eleven’s strange ballad “Two Girls” a “yardstick” for any country song: “That’s how good it’s gotta be,” he told Kruth. Its lyrics begin with an unsettling description of clouds that “didn’t look like cotton/They didn’t even look like clouds.” Van Zandt enters a dreamworld, encountering increasingly surreal figures. “Two lonesome dudes on an ugly horse” ask him where the action is; a woman called Jolly Jane “just lays around/And listens with her mouth.” The song ends with apocalyptic imagery:

It’s cold down on the bayou
They say it’s in your mind
But the moccasins are treadin’ ice
And leaving strange designs

“Two Girls” was written in Pasadena, at Van Zandt’s lowest point. The frozen bayou and its serpentine patterns are frightening enough, but even the song’s more prosaic elements point to his suffering: The ugly horse is heroin, and the lazy Jolly Jane a need that cannot be met. The seemingly upbeat chorus describing Townes’ two girls—“One’s in heaven and one’s below”—is about Leslie Jo Richards, a girlfriend who accompanied him to L.A. to record his fifth album, High, Low and In Between. They were in the studio when Van Zandt realized he had forgotten something. Richards volunteered to retrieve it and set out to hitchhike back to their condo. The driver who picked her up stabbed her more than 20 times before leaving her for dead. She made it to a nearby house to call for help before collapsing. Townes never forgave himself for her murder. While she was up in heaven, he was stuck down below with another girl who, he laments, “I do not know.”

Death and heroin haunt Seven Come Eleven. On “White Freight Liner Blues,” Townes is torn between love and hate for the drug. “White freight liner/Won’t you steal away my mind?” he pleads, before admitting that “it’s bad news from Houston/Half my friends are dying.” Rex “Wrecks” Bell, Van Zandt’s touring bassist, was one of those friends. “He would come get me and take me on the road to get me out of Houston,” Bell told songwriter Otis Gibbs. “Rex’s Blues” is dedicated to him, though he resented it. Bell points out that it could’ve been written for any number of people in their circle:

If I had a nickel I’d find a game
If I won a dollar I’d make it rain
If it rained an ocean I’d drink it dry
And lay me down dissatisfied

“The song captures what we were all doing. It was foisted upon me to be the focus of how we were all living,” Bell says. The song tells of their shared impatience with mundane life and their strategies for escaping it: gambling for money, spending it on booze, drinking to forget that they were all waiting around to die.

Clement was back in the producer’s seat for Seven Come Eleven, but by this point, he knew not to over-produce Van Zandt’s songs. The best tracks on the album are those where Townes is left alone to play and sing with minimal accompaniment. Townes could play delicately rolling melodies with finger picks or stronger, more percussive sounds with flat picks, and both styles could carry a song on their own. When Cowboy Jack adds his own touches, as with the addition of gentle backing vocals to the piano-driven ballad “No Place to Fall” or the eerie monastic chanting on the brooding “The Spider Song,” he usually enhances Van Zandt’s songs. More than ever before, Townes’ vision shines through unfiltered.

By this point, Van Zandt had fallen into a rhythm. He would record during the spring, hide out in Colorado over the summer, and then tour behind the new album in the fall. In September 1974, Bell was trying to kick heroin again, so Townes formed a band with Bell on bass and Mickey White on guitar for a tour through the Rocky Mountain region in support of the forthcoming album. Their friend Johnny Guess, who’d recently acquired a motor home that he dubbed the Blue Unit, was quickly recruited as tour manager and driver. Townes also brought along his new girlfriend, Cindy Morgan, then only 16 years old. The tour centered around a two-week residency at the Mangy Moose Lodge, a ski resort in the Teton Mountains. By the time they arrived there that winter, their group had expanded: Bell and Guess, both annoyed with Cindy, invited their girlfriends to fly in too, and the singer Richard Dobson joined as an opening act. The Mangy Moose had no vacancies, leaving the party of eight confined to the small motor home.

The group started to fall apart at the foot of the Tetons. They kept warm with butane and whiskey and added some LSD and cocaine for good measure. The longer they stayed, the less sure they were of their goal. The new year came and went with no sign of a release date for Seven Come Eleven, and it was doubtful that the crowd at the Mangy Moose would care much anyway. Van Zandt handed over more and more of his stage time to Bell and White for their incipient comedy-country duo, the Hemmer Ridge Mountain Boys. By the time they left Wyoming, the group’s nerves were frayed. In Denver they scored some heroin and began furtively shooting up in their bunks. Outside of Crested Butte, White stabbed Van Zandt’s stuffed dog, Spot. Later, Guess tried to stab Bell. They were glad to make it back to Texas alive.

Though it was ultimately disastrous, the Blue Unit tour was undertaken in good faith to promote Seven Come Eleven. “Townes tried to get tour support and advertising for the gigs. He clearly understood what promotion was about. He was loyal as the day is long and was still wondering when the new album was going to come out,” White told Kruth. They tried to get an explanation from Eggers to no avail. “It was becoming more and more clear that whatever hopes we had of the album getting out were just about gone. Every time we called Kevin and tried to find out what was going on with it, or try to communicate with him… It was just clear,” he recalled to documentary director Brown.

Many years later, Eggers would say that Van Zandt’s increasing drug use was the reason that he refused to release the album. “This was the last studio album I did with Townes,” he explains in the documentary. “[It was] in Nashville and this was when his drugs were really kicking in hard. I didn’t put this out for 20 years, I had such a bad feeling about the whole event.” In reality, Eggers himself was to blame. Poppy went bankrupt in 1973 and Eggers was eventually forced to sell the label’s assets to United Artists for an undisclosed sum. The state of his business was still in limbo during the Seven Come Eleven sessions. Eggers negotiated with Clement to delay payment for the studio time, which totaled $6,000. “We cut that record in my studio,” Cowboy Jack said in Robert Earl Hardy’s biography A Deeper Blue, “and Kevin never paid the studio bill. So I kept the tapes—for years. And he never did pay me.”

Rumor began to spread about the lost tapes. Musicians in Van Zandt’s circle worried that Clement had recorded over them out of spite. John Lomax III, who would later become Townes’ manager, called Seven Come Eleven “the missing link in his career. If that had come out right on top of The Late Great, it would have really been a whole ’nother thing.” Instead, Van Zandt’s career stalled and, without much else to do, he gave himself wholly over to his worsening drug abuse.

Townes moved to a trailer in Clarksville, an area west of Austin that had been cut off from the larger city. The African American residents of Clarksville endured the local government’s attempts to remove them to the east side, persisting despite a lack of services or even paved roads. Van Zandt and his friends soon cohered around Uncle Seymour Washington, a former blacksmith and amateur preacher who hosted his new white hippie friends at his famous barbecues. In James Szalapski’s classic documentary Heartworn Highways, a profile of the emerging outlaw country movement, Van Zandt plays “Pancho and Lefty” and “Waitin’ Around to Die” in Uncle Seymour’s living room. During the performance, tears roll down the older man’s face.

Though David Allan Coe was Heartworn Highways’ most successful subject, Van Zandt stole its spotlight through sheer force of personality. Carrying a bottle of whiskey, a can of Coke, and a BB gun, he introduces his dog Geraldine before his girlfriend Cindy. He gives Szalapski a tour of the land, which he claims is infested with giant rabbits. But the charming, fun-loving man in front of the camera was far different than the one behind the scenes. Townes and Cindy’s addictions were worsening, and they were dodging the filmmakers in order to shoot up.

Throughout their time in Clarksville, Van Zandt’s behavior became worrying. “It wasn’t a very productive time for him. He didn’t do too many gigs. He mostly sat around drunk all the time. He and Cindy were constantly at each other’s throats,” White told Kruth. The breaking point came when Townes and Bell, on a deranged drinking binge, jumped into dumpsters and covered themselves with filth. They then made a tour of bars and clubs where they would threaten to simply hang out unless they were given money to leave. Van Zandt was found that night unconscious in a dumpster and taken to Brackenridge Hospital in Austin, where he was admitted to the rehab program. He stayed for 10 days of the 45-day program before checking himself out.

It was obvious a change was needed. Townes and Cindy moved to a cabin outside of Franklin, Tennessee, about 20 miles south of Nashville. Van Zandt imagined it as a bucolic retreat where they would live off the land, hunting and chopping wood. “I think things might be OK. With the cabin and all I feel more settled,” he told Hedgepeth in 1977. “Leads me to believe I could be rooted somewhere and make it in this business, be ‘successful’ with the public.” But it was a retreat from the music industry as much as anything. “I’ve been on the road so long I’m tired of it. I’m indifferent to it. I’d rather sit home and drink and pick up royalty checks.” Soon life in Franklin was out of control too. Townes made daily trips to the liquor store in his old pickup truck and alternated between shooting heroin and shooting guns. One day, Van Zandt played three rounds of Russian roulette to make a point to his young acolyte Steve Earle. He survived death again, though the only lesson Earle learned was that his hero was dangerously unstable.

Van Zandt hadn’t written many songs since 1974. Instead, he treated his next record, 1978’s Flyin’ Shoes, as an opportunity to salvage the best tracks from Seven Come Eleven. Six of its 10 songs were originally on the lost album. The problem was that Townes was in no shape to record, and certainly could not capture the magic from those earlier sessions. Shortly before they were due at the studio, his neighbor and friend, Mike Ewah, crashed his truck into a tree on a liquor run. Townes was in the passenger seat and got thrown against the dash, breaking his right arm. He could no longer play guitar, but neither Eggers nor Van Zandt wanted to lose the studio time that they had booked with legendary Memphis producer Chips Moman, who decided that his session players could make up for Van Zandt’s parts. The band, which included consummate professionals like Billy Earl McClelland and a young Randy Scruggs, could play the songs, but they lacked Townes’ distinctive fingerpicking style.

Flyin’ Shoes is expertly produced, with every instrument as big and clear as the Texas sky. This has the marked disadvantage of giving Van Zandt’s voice, now noticeably tired, no place to hide. On Seven Come Eleven, he performed “Loretta,” an uptempo number about a barroom girl who’s perpetually 22, like he was singing through a sly grin. Townes can barely get through the new version, a wistful ballad that’s at odds with its lyrics about free and easy love. The original “Snake Song” is a short, moody sketch that Van Zandt delivers with real menace. On Flyin’ Shoes, it expands into a full-band arrangement, complete with goofy rattlesnake sounds. “You can touch me, if you want to/But I’ve got poison, I just might bite you,” Townes slurs, more toothless than threatening.

His new manager, John Lomax III, who was largely responsible for this brief flurry of activity, was soon forced out by Eggers. Lomax (a nephew of the famous folklorist) was convinced that his ouster was punishment for prying into Eggers’ business practices. Lomax uncovered what he called a “shell game” that had been ongoing since the advance from Van Zandt’s first contract went missing. “I was fixin’ to find out who was stealing the money and where it was going,” he told Hardy. Without Lomax on his side, Townes limped on through a few unsuccessful tours. His broken arm hampered his playing during the 1979 Flyin’ Shoes shows. The next year, his band was confronted with a series of canceled gigs on a tour booked by a shady promoter. Sometimes, they would arrive at the venue only to find that nobody was expecting them. Townes retreated back to Franklin with empty pockets and opened the door to an empty cabin. Cindy had abandoned him and moved to Canada.

This was another low, but Van Zandt’s luck was about to change. Emmylou Harris covered “If I Needed You” in 1981, making it to No. 3 on the country charts. Then in 1983, Willie Nelson and Merle Haggard covered his defining song, “Pancho and Lefty,” which went to No. 1 on the country charts. Townes’ dream of sitting home, drinking, and picking up royalty checks had come true. He also met Jeanene Munsell, who would become his third wife and the mother of his second son, Will, and only daughter, Katie Belle. These were all reasons to slow down and enjoy a life of quiet domesticity. Van Zandt struggled to quit drinking, but could never piece together more than a year of sobriety. He toured frequently, employing Eggers’ brother Harold as road manager to monitor his drinking and ensure that he could at least start each show. He played some blazingly good concerts, but just as often he was so drunk that he would mumble his songs and fall off his stool. Townes had seemingly lost all interest in recording, as well. Throughout the ’80s, he only released one studio album, At My Window—a far cry from the six albums in the half-decade that launched his career.

Seven Come Eleven was finally released in 1993 as The Nashville Sessions, nearly 20 years after it was recorded. How the tapes survived is unclear. One story is that Eggers, hearing that Clement planned to erase the tapes, had snuck into the studio and transferred the masters onto cassette back in 1974. But by the ’90s, the release was hardly newsworthy: It was an obscure album by a cult singer-songwriter, and 10 out of 12 songs had already appeared on Flyin’ Shoes, At My Window, or various live albums. The momentum of Van Zandt’s early years had dissipated across two decades of hit-or-miss tours and infrequent recordings. The brilliance of the record that he was sure would be a hit had been dimmed through the later, lackluster versions of its best songs.

Van Zandt’s last album was set to be recorded in Memphis in December 1996. Sonic Youth drummer Steve Shelley had reached out to Townes and offered to produce the sessions, which would be released on Thurston Moore’s Ecstatic Peace! imprint. But a few days before the studio date, Townes fell down outside his home. Though he didn’t realize it at the time, he had fractured his hip. He arrived at the studio in a wheelchair, visibly in pain. He could hardly sing, much less play guitar. Growing increasingly frustrated, he would demand more liquor from Harold. Shelley tried to coax out some usable takes but soon found it impossible. He reluctantly cancelled the sessions.

Finally, Van Zandt agreed to go to the hospital as long as he was accompanied by Jeanene. The doctors told them that he would need surgery at once. The next day, Townes was suffering from delirium tremens, shaking and hallucinating. Doctors recommended an immediate detox, but Jeanene had witnessed Townes suffer during similar programs and felt he couldn’t survive another attempt to quit drinking. Against medical advice, she signed him out of the hospital.

Back at home, Townes settled down with some vodka and a small plate of food. His doctors refused to give him pain medication if he was going to drink, but after sipping on the liquor and taking Tylenol, he seemed to get better. Jeanene went to call friends and update them on his improved condition. But later that evening, his son Will found him unresponsive. Jeanene’s panicked attempts to revive him were fruitless. This time he was gone, really gone, in all three ways at once.