Willie Nelson’s Long Encore

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Willie Nelson has a long history of tempting, and cheating, death. In 1969, when his home in Ridgetop, Tenn., caught fire, he raced into the burning house to save two prized possessions, his guitar and a pound of “Colombian grass.” He has emphysema, the consequence of a near-lifetime of chain smoking that began in childhood, when he puffed on cedar bark and grapevines, before turning to cigarettes and then — famously, prodigiously — to marijuana. In 1981, he was taken to a hospital in Hawaii after his left lung collapsed while he was swimming. He underwent a voluntary stem-cell procedure in 2015, in an effort to repair his damaged lungs. Smoking has endangered his life, but it also, he thinks, saved it: He has often said that he would have died long ago had he not taken up weed and laid off drinking, which made him rowdy and self-destructive. Now, in his late 80s, he has reached the age where getting out of bed each morning can be construed as a feat of survival. “Last night I had a dream that I died twice yesterday,” he sang in 2017, “But I woke up still not dead again today.”

Still, some close calls are closer than others. One evening in early March 2020, the singer and his wife, Annie, were sitting outside the sprawling log cabin residence at their ranch in Spicewood, Texas, in the Hill Country about 30 miles northwest of Austin. It was warm and clear. The sun was going down. “We were watching the sunset,” Annie recalled not long ago. “And these little lights started to zip across the sky. The first one kind of flashed past in the distance. Then there was a second, which went by a little closer. All of a sudden, the light went right past us — like, two feet over Will’s head.”

The couple scrambled into the house and got down on the floor. According to Annie, the neighbors were “having another one of their gun parties. Apparently they got drunk and left a bunch of kids with semiautomatic rifles.” The police, she said, explained that the lights came from tracer bullets. “I said, ‘Are those even legal?’ But of course, nuclear weapons are legal in Texas. I told the police to please just pass along this message: ‘Dude, you don’t want to be the one that kills Willie Nelson. Especially in Texas.’”

“Anyway,” she said, “that was the beginning of our Covid quarantine.”

Days earlier, Nelson played for a crowd of more than 70,000 at the Houston Livestock Show and Rodeo. Now cities were going into lockdown. Given Nelson’s age and underlying conditions, a deadly virus that attacked the respiratory system was a frightening proposition. So the Nelsons hunkered down in Spicewood, where they were joined by their adult sons — Lukas and Micah, both musicians — and Micah’s wife, Alex. For the first time in decades, Willie Nelson was staring at an empty calendar.

For several months, only Annie left the ranch, once a week, to buy groceries. Nelson and his sons played lots of poker, dominoes and chess. Nearly every evening, the three would gather in the living room with their guitars to sing Nelson’s songs and old favorites by the likes of Hank Williams and Roger Miller. “It kept us sane, sort of,” Lukas says. “My dad was bored. He was anxious. He was in a state of existential dread, fearing that this thing he’d done his whole life would never come back.” Nelson tried to keep busy, meeting with a physical therapist for online sessions, sitting for Zoom interviews and performing livestreamed benefit concerts. But his famous tour bus sat by the entrance to the ranch, uncharacteristically idle.

Nelson has spent much of his life on tour buses, answering the siren call of the Interstate and the concert hall. “I can’t wait to get on the road again/The life I love is making music with my friends,” he sang, decades ago. There are thousands of songs about roving troubadours, but “On the Road Again” must be the most joyful and unabashed. For Nelson, barnstorming the country with a hot band is pure freedom. There was a moment, in the 1990s, when he pulled himself off the road, signing a contract for a six-month residency at a theater in Branson, Mo. But his cabin fever grew so acute, he wrote in his autobiography, that he took to “pitching a big sleeping tent in my hotel room and pretending I was out in the woods.”

Now, during the pandemic, he was marooned again. “Every day,” he says, “it was more and more like a prison sentence.” Sometimes, he would sit in his parked tour bus, “just to pretend I was going somewhere.”

“At the end of every tour, Will talks about retiring,” Annie says. “ ‘I think I might retire.’ But then we’ll have a conversation: ‘Well, what would you do if you retired?’ We both know the answer: Just lay down and die. It’s impossible to imagine him not being out there.”

For as long as anyone can remember, Nelson has been opening his concerts with “Whiskey River.” No one is certain when he started; when you’ve had a career as long as his, the math can get fuzzy. A newspaper reviewer once wrote that the song had been Nelson’s opening number “since the dawn of time,” a claim that stretched the truth, but not by much. The best guess is that it was installed as the set-opener around 1974, which would mean Nelson has sung it at the start of something like 6,500 shows. When you take your seat at one of his concerts, you know the scene that will unfold: A small man with a bandanna and braids will amble onstage, strap on a scuffed nylon-string guitar and launch into a famous chorus. “Whiskey river, take my mind/Don’t let her memory torture me/Whiskey river, don’t run dry/You’re all I’ve got, take care of me.”

That’s more or less what transpired this April 29 at Austin’s Moody Center, a new 15,000-seat arena on the campus of the University of Texas. Some 9 months earlier, Nelson’s pandemic concert moratorium had come to an end. That night, he was a warm-up act, opening for another legend, George Strait — at 70, a spring chicken compared with Nelson, and by some measures the most popular country artist of all time, with dozens of No. 1 singles and album sales of nearly 70 million.

But Nelson doesn’t play second fiddle to anyone, especially in Austin. The Moody Center sits less than a mile from the university building that, for decades, housed the soundstage for “Austin City Limits,” the live-music TV showcase indelibly associated with Nelson and the outlaw-country movement he spearheaded in the 1970s. Today, “Austin City Limits” is taped in a theater on Willie Nelson Boulevard, the downtown thoroughfare where you’ll find an eight-foot-tall Willie Nelson statue, cast in bronze. There are other works of Nelson-themed public art around town, including a giant “Willie for President” mural that is a magnet for Instagrammers. Shops are full of Nelson merchandise: bobbleheads, shot glasses, T-shirts emblazoned with song lyrics (“Roll Me Up and Smoke Me When I Die”) and bad puns (“Austin is Willie Weird”). George Strait might be a megastar, but in Austin, and nearly everywhere else, Willie is a deity. In 2019, Strait recorded “Sing One with Willie,” a cheeky complaint about how Nelson — who has performed duets with countless artists, from Sinatra and Joni Mitchell to Snoop Dogg and Jessica Simpson — had never bestowed the honor on Strait himself.

It was just after 8 p.m. when the house lights dimmed and Nelson took the stage, wearing a straw cowboy hat and a T-shirt that read “I Stand With Ukraine.” Recently, he had switched to performing while sitting down, a concession to age. Video screens suspended from the ceiling captured close-ups of the singer: handsome, white-bearded, with a face as craggy and weather-beaten as a desert outcropping. He gave his usual greeting (“How y’all doing?”), hammered on a chord a half-dozen times and, sure enough, the strains of “Whiskey River” rippled across the arena.

When Nelson first recorded the song, in 1973, it was an outlaw-country anthem, a woozy blend of honky-tonk and funk and blues — a sound more redolent of weed than whiskey. Its lyrics sketched the story of a spurned lover with a death wish; it was the testimony of a drowning man. But at the Moody Center, Nelson delivered it with a sly twinkle, like a song about a pleasure cruise. It was a festive occasion, after all: Nelson’s 89th birthday, and also the release date for “A Beautiful Time,” his 97th studio album (give or take; there are conflicting counts). It was unclear how many of those in attendance were aware of these milestones, and Nelson didn’t call attention to them. He simply went to work, leading his four-man band through a set that featured hits (“Always on My Mind”), classics from his songwriting catalog (“Crazy”), jazz standards (“Georgia on My Mind”) and hymns (“I’ll Fly Away”).

A Willie Nelson concert is a study in efficiency. He packed 20 songs into an hour, dispatching with most in three minutes or less, while keeping the banter to a bare minimum. But those brief, brisk songs contained multitudes. “The reason Sinatra was my favorite singer was his phrasing,” Nelson told me. “He never sang a song the same way twice. I don’t think I do either.” Nelson is indeed one of music’s great iterators, with a Sinatraesque knack for daubing in different colors, rendering old songs in revelatory new ways. His gift is to make that art seem artless, camouflaging technique with naturalism. His unruffled vocal tone is unmistakable and unchanging; songs roll out as natural as speech, as if he were not singing so much as thinking out loud. These effects rest on Nelson’s rhythmic play: His vocal phrases and guitar solos glide over the meter, lagging behind the beat or charging ahead, bringing suspense to every note and syllable. There is a term for this kind of derring-do — rubato — but Mickey Raphael, Nelson’s longtime harmonica player in the road band known as the Family, puts it another way. “That’s Willie’s prerogative,” Raphael says. “He goes where he goes. Our task is to follow him.”

It’s not an easy gig. At the Austin show, Nelson’s regular bassist, Kevin Smith, was sidelined with Covid, so he had brought in Robert Kearns, who normally plays with Sheryl Crow. Kearns had less than a day’s notice; the band never rehearses and, “Whiskey River” aside, doesn’t have a set list. Nelson sometimes counsels musicians to feel, not count — to disburden themselves of metronomic ideas about tempo and go with the flow. But that’s easier said than done, and you could hear Kearns laboring to keep track of Nelson’s floating cadences and hairpin turns. “Willie pulled out every trick, every idiosyncrasy,” Raphael said later. “Robert’s a great, great bass player. But all he could do was, you know, just kind of hang on.”

Nelson finished the set with a jaunty rendition of an old Mac Davis number, “It’s Hard to Be Humble.” About 90 minutes later, he reappeared onstage, joining Strait for a couple of duets. They did “Sing One With Willie,” a goofy crowd-pleaser, and the Townes Van Zandt ballad “Pancho and Lefty,” featuring a searching guitar solo from Nelson. As Nelson made his way offstage, Strait told the crowd, “You know, it’s Willie’s birthday,” and then led a chorus of “Happy Birthday.” Nelson boarded a golf cart, which whisked him through the audience and out of the arena. Soon he was on his bus, rolling through Austin, on his way out of town.

The careers of successful musicians tend to follow predictable patterns. You break through in your 20s and perhaps hit your prime in your early 30s. Talent knows no age limit, but inspiration often has a sell-by date. As midlife sets in, you may lose contact with the muse. Tried-and-true moves grow stale, sounds and styles that once brimmed with character curdle into caricature. The day-to-day demands on musicians exact a greater toll. The thrill of life on the road fades, and the bummers — loneliness, boredom, long hours, bad food — become harder to bear.

Willie Nelson is the exception that proves every rule. He hit his stride as a recording artist around age 40 and reached superstardom at 45. He has kept up a relentless pace ever since, recording thousands of songs while averaging more than 100 live dates per year, decade after decade. In 2022, his compulsion to sing and pick his guitar and ramble the roads is undiminished and, evidently, unappeasable. “Sometimes we’ll be off the road for three weeks or a month,” says Raphael, who has played with Nelson for 49 years. But then: “I’ll get a text from Willie, out of the blue, at some random hour of the day or night: ‘Let’s pick.’ The break might have just started, and he’s ready to get back out there.”

As Nelson has rounded the bend into old age, another unusual thing has happened: He has been making more music. He has had a very busy 21st century, producing a staggering 36 albums of new material since the turn of the millennium. He has recorded collections of children’s music and songbook standards and country-and-Western jukebox hits. He has released tribute albums to Sinatra, to George and Ira Gershwin, to the songwriter Cindy Walker. He has done album-length collaborations with indie rockers, with Western-swing revival bands, with Wynton Marsalis and members of the Lincoln Center Jazz Orchestra. He made a gospel-themed album with his sister and four of his children. He put out a reggae record, and it wasn’t embarrassing. He’s said to have hundreds more recent recordings in the can. The Willie Nelson of 2022 is an anomaly, perhaps unprecedented in popular music: His discography stretches back to the Eisenhower era, and he remains one of America’s busiest working musicians. “It’s a decent job,” he says. “Best one I’ve had, at least.”

In the past five years alone, Nelson has produced nine albums. On these records we hear more than the sound of a famous voice reinterpreting familiar material. Nelson’s catalog of original songs has been growing and taking on heft: Many new songs find him reckoning with the weighty matter of his own dwindling days. Death has always had a place in Nelson’s work. (A singer steeped in the earthy existentialism of country and blues could hardly avoid the topic.) But in recent times, it has become his Topic A.

This may be shrewd business. Albums of this sort are recording-industry mainstays; Nelson’s old pal and collaborator Johnny Cash won critical raves for a string of late-life releases that focused on his own impending demise. But where Cash’s mortality music was brooding and gothic, Nelson’s is Nelsonian: mischievous, droll, intrigued by cosmic conundrums and amused by the state of his own mortal flesh. The songs unspool in the voice of a man who has gazed into the abyss and come back drawling punch lines: “Heaven is closed and hell’s overcrowded/So I think I’ll just stay where I am.” Sometimes he allows himself a flight into the mystical, imagining his transmutation into a “blue star” in the night sky, or envisioning a jam session in the afterlife with departed musical comrades. Sometimes his jokes verge on metaphysical riddles: “I don’t go to funerals/I won’t be at mine.”

“Death is just a pretty good subject to write about,” he says. “It’s good material.”

When tracer bullets aren’t flying overhead,the land that Nelson christened Luck Ranch is a rather nice place to spend time. (“When you’re here, you’re in Luck,” he is fond of saying. “When you’re not here, you’re out of Luck.”) The ranch rolls across 700 acres, dotted with cedar and juniper trees. Like much of the region’s pastureland, the Nelsons’ acreage has been damaged by overgrazing and erosion, and the couple has undertaken a program of regenerative agriculture to restore the soil and revive the native flora. Dozens of horses wander the ranch; most are rescues, adopted so they wouldn’t be sent to the slaughterhouse. For years, Nelson was prone to wandering the property himself, usually at high velocity. “I liked to bust through those cedars,” he says, “either on a horse or in a pickup truck.”

The ranch is home to other animals too: sheep, pigs, chickens. This came in handy during the Covid lockdown. “If we were low on eggs,” Annie says, “I could go grab some from under a chicken butt.” She cooked the family meals, and to streamline the operation, the Nelsons came up with a menu they nicknamed the Pandemic Pantry: vegan meatloaf on Mondays, tacos on Tuesdays, etc. (“The deal was: If you want something else, make it yourself,” Annie says.) Tensions can creep in when you’re sequestering for long stretches, perhaps especially among strong-willed people with artistic dispositions. The Nelsons maintained harmony with a set of rules that have become famous among fans, reproduced on swag for sale at shows:

1. Don’t be an [expletive].

2. Don’t be an [expletive].

3. Don’t be a goddamn [expletive].

“They’re good rules, but we’ve all broken them,” Nelson says. “I’ve definitely broken Rule No. 3. My loved ones will confirm that.”

Annie is Nelson’s fourth wife. She is also, he has often said, the love of his life. They met in 1986, in Arizona, on the set of the made-for-television Western drama “Stagecoach,” where she was working as a makeup artist. They first bonded over the question of Nelson’s hair, which they agreed he did not need to cut short in order to play the role of Doc Holliday. But a relationship seemed unlikely. Ann Marie D’Angelo was 30, Nelson was 53. She had vowed never to date celebrities or get involved with men who had messy marital backgrounds or children. Nelson was separated but not yet divorced from his third wife; he had five kids, one of whom was born to the woman who would become Wife No. 3 at a time when he was still married to No. 2. But Nelson and D’Angelo were both quick-witted, tough-minded and warm — a good match. He pursued her ardently; they fell in love. Lukas Autry Nelson was born on Christmas Day 1988; Jacob Micah Nelson arrived in May 1990. Willie and Annie were married in 1991.

Nelson considers Luck his true home, but the Nelsons raised their sons far away, in an oceanfront house on the northern coast of Maui. Nelson, of course, was often gone, on the road up to 200 days a year. Lukas and Micah grew up surrounded by musical equipment and taught themselves to play, bashing out classic-rock songs in a band room near the little building in the rear of the house where Nelson gathered with friends when he was not on tour. While Nelson got high and played poker, he followed his sons’ increasingly tighter and more assured renditions of Jimi Hendrix and Pink Floyd songs. “I always looked at music as a way to get closer to my dad,” Lukas says. “There was never any pressure about it. But I knew that he loved music so much, and that if I did it, too, I’d make him happy, and we’d be able to spend more time together.”

Today Lukas, 33, is a star in his own right: a gifted songwriter and guitarist with a reedy vocal tone reminiscent of his father’s. His acclaimed roots-rock quintet, Lukas Nelson and Promise of the Real, has released eight full-length albums and served as Neil Young’s backing band. (They were also the backing band for the fictional singer played by Bradley Cooper in the 2018 “A Star Is Born” remake, whose soundtrack includes eight songs co-written by Lukas.) Micah, 32, is a sometime Promise of the Real member himself, joining the band on its tours with Young; he also records solo work, which tilts toward the noisy and experimental, under the moniker Particle Kid. The nickname was coined one day when he was 14 and his (very stoned) father tried and failed to say the phrase “prodigal son.”

Nelson has played and recorded with his daughters Paula, 52, and Amy, 49. Now Lukas and Micah have become his musical right-hand men, with an intimate view of his late-life creative burst. “He’s been making some of the best music he’s ever made,” Micah says. “He’s singing and writing songs now that he couldn’t have written at 30 or 40. He’s decorating the story of his life, and he’ll continue to do it till he’s no longer breathing.”

A theme that has run through Nelson’s songs from the beginning is his hunger for the road. It was there, obliquely, in his very first single, written and recorded in 1957, a lament about a failed romance whose refrain is a nomad’s itchy motto: “This is no place for me.” Perhaps his most intriguing disquisition on the subject is “Still Is Still Moving to Me” (1993), one of his signature songs, a kind of koan set to a backbeat and spaghetti-Western guitar. “I can be moving or I can be still,” he sings. “But still is still moving to me.” Precisely what he’s getting at is uncertain; in the song, he concedes he is straining to express elusive and ineffable ideas. “It’s hard to explain how I feel/It won’t go in words but I know that it’s real.”

“He wants to move,” Lukas says. “He needs to move. He needs to roam the land and play his music and be free. He’s been moving since he was a very young kid. He’s been in the hustle of the times ever since he left the cotton fields in Abbott, Texas.”

Abbott, a small town about 25 miles north of Waco, is where Nelson was born, in 1933. When he was 6 months old, his young parents split up, leaving Willie and his 2-year-old sister, Bobbie, in the care of their paternal grandparents. Nelson sees this as a stroke of good fortune. His grandparents, Nancy and Alfred — “Mama and Daddy Nelson” — were devoted and conscientious caretakers. They were also musicians. Mama gave singing lessons from home; Daddy, a blacksmith, played guitar. By the time Willie was 6, he had his first six-string and was learning to play chords and write songs. Bobbie was a piano prodigy who seemed to instantly assimilate new styles; she would become her brother’s enduring musical collaborator and “closest friend for a whole lifetime.”

To grow up in rural Texas during the Depression was to know an existence defined by struggle and want. But musically, Abbott held riches. Willie basked in the hymns at the United Methodist Church. The radio transmitted enthralling sounds, too: the Western swing of Bob Wills and his Texas Playboys, the jazz of Louis Armstrong and Duke Ellington, Tin Pan Alley hits like “Stardust” and “All the Things You Are.” Willie was also captivated by the music he heard at movie matinees, especially the drifter anthems sung by Hollywood cowboys like Gene Autry and Roy Rogers. And he worked alongside his sister and grandmother in the cotton fields, where other songs rang out. “There were a few of us white people out there,” he says. “But over here, there’d be Mexicans singing mariachis. And over there, you’d hear a Black guy singing the blues.” The trumpeter and composer Wynton Marsalis recalls a revealing backstage moment. “It was me, Willie, B.B. King, Ray Charles and Eric Clapton,” he says, all shooting the breeze — “and Willie said: ‘Well, gentlemen, I think I’m the only one here who actually picked cotton.’” Everyone burst into laughter. “Willie has had some profound experiences,” Marsalis says. “His music, his knowledge, comes from a long, long way.”

At 10, Nelson joined a Czech polka band that played beer halls; when he and Bobbie were teenagers, they formed a dance band with Bobbie’s young husband. He graduated from high school in 1950, served in the Air Force for nine months (he received a medical discharge for a bad back), then tried college at Baylor University in Waco before dropping out to pursue music. He married his first wife, Martha, at 19, and had three children in short order. For the next several years, he bounced around the country while working a series of jobs (saddle maker, dishwasher, door-to-door salesman) and honing his craft.

Eventually he made his way to Nashville, where he gained a reputation as an uncommonly gifted songwriter. Had he never succeeded as a performer, the handful of hits he wrote in the late 1950s and early ’60s might have secured his legend anyway. Songs like “Family Bible,” “Hello Walls” and “Funny How Time Slips Away” were miracles of concision, speaking volumes in spare words while smuggling in melodic and harmonic twists. The torch song “Crazy,” a hit for Patsy Cline in 1961, poured out heartache in a swooping tune that sounded more jazz than country. “Night Life,” a hit for Ray Price two years later, showed Nelson’s genius for poetic plain-speaking: “The night life ain’t no good life/But it’s my life.”

“He’s one of those extraordinary songwriters who embodies a genre and transcends it,” Elvis Costello says. “He’s got an ear for changes, for passing tones, that aren’t found in country songs at all. I think I knew ‘Funny How Time Slips Away’ for 20 years before I realized the ‘Nelson’ on the songwriting credit was Willie Nelson — I assumed it was an old jazz ballad.”

Nelson got a record deal with RCA Victor in 1964 and released a string of LPs, but he bridled under the label chief, Chet Atkins, who favored the ornate production of the so-called Nashville Sound. In 1969, Nelson bought a new guitar, a nylon-string Martin N-20, which he fitted with a pickup to produce a tone reminiscent of one of his musical gods, the jazz guitarist Django Reinhardt. He named the guitar Trigger, after Roy Rogers’s horse, and before long his fingers had worn a hole in the soft spruce above its bridge. His music was getting more scraped and scarred, too, its Music Row sheen peeling away as he sought a starker sound. In 1971 he recorded “Yesterday’s Wine,” a concept album about the life and death of an “imperfect man.” He thought it was the most honest LP he’d ever made; an RCA executive called it “some far-out [expletive] that maybe the hippies high on dope can understand.”

Nelson had run his course in Music City. He moved back to Texas and considered taking up pig farming. But while visiting Nashville in 1972, he attended a house party where songwriters were playing their tunes and, late at night, offered some of his own new material. Among the small crowd still present was the Atlantic Records executive Jerry Wexler, who astonished Nelson by offering him both a contract and creative freedom. (Forget commerce, Wexler said: “You’re going for art.”) What followed was groundbreaking: The LPs “Shotgun Willie” (1973), “Phases and Stages” (1974) and “Red Headed Stranger” (1975) cleared a path forward for country music by looking to the past, combining the attitude and ambition of album rock with the raw, rootsy sounds of honky-tonk, bluegrass, folk and gospel.

Nelson’s new direction reflected the ferment of his home in Austin, where hippies and rednecks rubbed shoulders and a funky new species, the hippie-redneck, emerged. The figureheads of this scene were Nelson and the band he assembled after moving to town in 1972. The Family — Bobbie Nelson (piano), Mickey Raphael (harmonica), Bee Spears (bass), Jody Payne (guitar) and Paul English (drums) — wore long hair and thick beards, jettisoning Grand Ole Opry rhinestones for jeans and T-shirts. The look was anti-establishment, with a hint of menace. English was the group’s muscle, ready to straighten things out when club owners stiffed the band; he was rumored to carry two guns at all times. (Nelson immortalized their relationship in one of his most beloved songs, “Me and Paul.”) A platinum-selling 1976 compilation, “Wanted! The Outlaws,” gave the movement a name and established its commercial bona fides: “Outlaw country” would prove a sales juggernaut, minting new stars (Waylon Jennings, Kris Kristofferson) and invigorating the careers of renegade veterans (Johnny Cash, Merle Haggard).

The biggest success was Nelson. “Red Headed Stranger” was his first true hit album. Then, in 1978, came a blockbuster, “Stardust,” a collection of standards that stayed on the country album charts for a full decade, establishing the cowboy warbler as an interpreter of the American Songbook on par with the greatest jazz vocalists. In the years that followed, Nelson reached superstardom, attaining a presence in popular culture that arguably no other country singer has, unless Taylor Swift counts as a country singer. He starred in motion pictures. He visited the White House on numerous occasions. (On one visit, he got high on the roof with President Carter’s son Chip.) He did a public service announcement for NASA alongside Frank Sinatra and had a huge international hit with Julio Iglesias, the oily and absurd “To All the Girls I’ve Loved Before.” He was one of few country artists to join the pop, soul and rock demigods on the charity single “We Are the World.”

Nelson’s renown is bound up with his image as a rebel, a reputation enhanced by his yearslong showdown with the Internal Revenue Service (which seized a good share of his assets in 1990) and his multiple busts for marijuana possession. A decent case could be made that he is history’s most famous pothead, the man whose likeness should be carved into the golden bong of posterity. For decades, he has been an advocate for legalization, and in 2015 he launched the cannabis company Willie’s Reserve (tagline: “My stash is your stash”). You can hear a stoner sagacity in both his lyrics and the way he sings them — in the freedom of his rubato, his gliding excursions through musical space-time.

Nelson is a scrambler of categories. He’s down-home and urbane, countercultural and traditional, a political progressive who occupies the loftiest perch in America’s most conservative musical genre. (Presumably, many fans in his home state take issue with his endorsement of Beto O’Rourke and his call to support Texas Democrats in their fight against voter suppression.) It’s impossible to name a white performer more steeped in qualities we associate with Black music — syncopation, improvisation, blue notes, the push and pull between sacred and earthly yearnings — yet not a trace of minstrelsy can be detected in his sound. He is always — indubitably, irreducibly — Willie Nelson.

The most striking feature of his career is not length but breadth. There appear to be no songs he can’t sing and few he hasn’t. Though nominally a country artist, he is really more like an American musical unconscious, tapped into the deepest wellsprings of popular song. He has a way of making everything he sings — from “Amazing Grace” and “Danny Boy” to “Time After Time” (the Cyndi Lauper song) and “The Rainbow Connection” (the Kermit the Frog song) — sound Platonic and primordial. The only comparable figures, according to Marsalis, are Ray Charles and Louis Armstrong. “To be great in all the forms that Willie is great in — it’s extremely rare,” he says. “He has whatever that spiritual thing is, that thing you can’t describe. It’s like a shamanistic type of insight into the nature of all things. From that place of understanding, he can play anything he wants to play that comes out of the American tradition.”

For a guy who makes so many records, Nelson doesn’t spend much time in recording studios. He is a legendarily speedy worker. “He records fast because he has zero patience,” says Micah Nelson. There are tales of sessions in which Nelson materialized to make a guest appearance on someone’s record, laid down a vocal track or guitar solo in a single spotless take and then left as quickly as he’d come, roaring off on his tour bus.

Pedernales Recording Studio, which Nelson built in the early 1980s, sits one mile from Luck Ranch, adjacent to a 9-hole golf course Nelson also owns. Buddy Cannon, 75, is a veteran Nashville songwriter and producer who has overseen much of Nelson’s recent work there. The two first met in the late 1970s in Amarillo, Texas, at a promotional concert, when a mutual friend asked Cannon if he wanted to smoke a joint with Nelson. (“It’s a pretty good way to meet Willie Nelson, smoking a joint in a broom closet,” Cannon says. “I probably wasn’t the first guy to meet him that way.”) They met again three decades later, in Nashville. Cannon was producing a 2007 Kenny Chesney session for which Nelson had agreed to sing a duet. Nelson liked the sound of the recording so much that he hired Cannon to produce his next album, “Moment of Forever.” They’ve gone on to make 15 more albums, with Cannon assuming not only mixing-board duties but also a role as Nelson’s songwriting partner.

Their working relationship is one neither could have envisioned when joints were passed in broom closets: They write via text message, volleying lyrics back and forth. Usually Cannon will arrive at the studio with a rough outline of a tune, but it is Nelson who does the finishing work, improvising while the tape rolls. As a producer, Cannon’s goal is to be as unobtrusive as possible, offering the cleanest view of what he calls Willie World. “I try to treat his music the way it treats us,” Cannon says. “I just try to capture the Willie vibe.”

Sometimes the vibe arrives unbidden, overnight, in Cannon’s iPhone. On the morning of July 29, 2020, he awoke to a text from Nelson, the first verse of a prospective new song.

“Write a verse,” Nelson added. “If you like it.” Cannon came up with some lines about how wisdom is dispensed in dreams and through the intercession of spirits, and the songwriters traded messages until Nelson was convinced they’d done the job.

The result, “Energy Follows Thought,” is the emotional — or cosmological — centerpiece of Nelson’s latest album, “A Beautiful Time.” It’s a stately ballad, crooned by Nelson in confiding tones over shivering, echoing production. A kick drum beats out a low, steady pulse; Nelson’s guitar rumbles and probes. The sound is both intimate and gigantic, like a lullaby sung in an amphitheater on the moon. Nelson says the song is “one of my philosophies.” To Mickey Raphael, the harmonica player, it “scratches on quantum physics.” But with its talk of ghostly visitors that speak through dreams, “Energy Follows Thought” may well be another lion-in-winter anthem, one more shadowy rumination on what lies beyond. The cover of “A Beautiful Time” shows Nelson striding, guitar in hand, into a blazing sunset.

“He’s lost so many people, so many loved ones,” Annie says. In 1991, Nelson’s son Billy, one of the three children from his first marriage, committed suicide at age 33. Those close to Nelson say that he’s been hit hard by the deaths of friends and fellow travelers, like Cash and Haggard and Ray Price. Recently he has endured the losses of even closer musical compatriots. Paul English passed in February 2020. On March 10 of this year, Bobbie Nelson died in hospice care in Austin. “I don’t want to be the last man standing/On second thought, maybe I do,” Nelson sang in 2018. It was a good line, another wisecrack at Pale Death’s expense. But truth lurks behind the quip. It is hard to be the last man standing. And he really doesn’t go to funerals.

On May 4, less than a week after Nelson’s 89th birthday, Willie and Annie were in Nashville. The singer woke up in the middle of the night, on his tour bus, struggling to breathe. A health care worker was summoned. A rapid PCR test was administered. Nelson was Covid positive.

“I had a nebulizer on the bus,” Annie says. “I started everything I could at that point, including Paxlovid. He had the monoclonal antibodies. He had steroids.” They drove through the night and made it home to Spicewood, where Annie got a mobile medical unit out to the ranch. “We turned the house into a hospital,” she says. “There were a couple of times when I wasn’t sure he was going to make it.”

“I had a pretty rough time with it,” Nelson allows. “Covid ain’t nothing to laugh at, that’s for sure.”

Six days after taking ill, he was out of the woods. Two weeks after that, he was back on tour, playing a pair of shows in New Braunfels, Texas. From there it was on to Little Rock, Ark.; Oklahoma City; Camdenton, Mo.; Wichita, Kan.; El Dorado, Ark.; St. Louis; Grand Rapids, Mich.; Noblesville, Ind.; and Franklin, Tenn.

On the afternoon of June 29, the Honeysuckle Rose — the fifth custom-designed Willie Nelson tour bus to bear that name — pulled into a parking lot outside a hotel in Louisville, Ky. His bandmates and road crew usually stay in hotels, but Nelson himself only ever sleeps on the bus. He has spent many nights there — many years, if you crunch the numbers. There are occasions when he has chosen to sleep on the bus even when it was parked in the driveway of one of his palatial homes. “There’s everything you need right here,” he said, from the kitchen area. “Good food to eat. Two bathrooms. A shower. A nice bed. If I felt like writing a song, I bet I could find a guitar in here somewhere.”

The Honeysuckle Rose looms large in Willie lore. Vast sums have changed hands on the bus, in games of poker and dominoes. A president has visited (Carter), as have innumerable musicians, movie stars, journalists and members of law enforcement, like the Louisiana State Police officers who paid a visit in 2006 and extracted 1.5 pounds of marijuana and 3 ounces of psychedelic mushrooms. Many have boarded the Honeysuckle Rose with a spring in their step and, sometime later, staggered off, having taken too many hits of Nelson’s powerful weed. Often one hit was too many.

The scene these days is less freewheeling. Nelson is supposed to have given up smoking marijuana in favor of an edibles-only regimen. (“It wasn’t good for my lungs,” he says.) The pandemic has also brought changes to his touring routine. With occasional exceptions, like the birthday show at the Moody Center, he plays only outdoors. Daily Covid tests are mandatory for everyone in the band and crew; masking is obligatory backstage. Onstage, musicians are instructed to give Nelson at least six feet of room. The most zealous enforcer of these protocols is Annie Nelson. “If I have to be the bad guy to keep him safe, I’ll be the bad guy,” she says. “A virus doesn’t care who you are, what you believe, how famous you are.”

Health concerns have forced Nelson to scale back his touring schedule. His concerts are carefully spaced, with far fewer dates stacked up, giving the singer time to rest and recuperate. He’s on the road again, but he may never again hit the 100-show-​per-year marker that was, for years, the bare minimum.

Mark Rothbaum, Nelson’s manager, does not regard his 89-year-old artist as a legacy act. “I want everyone to know him, everyone to see him,” he says. “If he’s playing and it’s 3,000 people, well, I’d rather it be 300,000 people.” Nevertheless, legacy management — getting an official history on the record — is a priority. Live recordings are being exhumed from archives. A multipart documentary in the works aims to chronicle Nelson’s “extraordinary life and career.” The singer himself has co-authored a number of books — memoirs, folksy works of fiction, collections of essays and aphorisms. The latest, “Me and Paul: Untold Stories of a Fabled Friendship,” will be published in September.

And there are the new records. The next studio album — No. 98, give or take — is a tribute to the Nashville songwriting ace Harlan Howard; it will probably be out early in 2023. “My attitude always is: What’s next?” Rothbaum says. “What’s the next record? Where’s the next show? Where’s the bus headed? Willie likes to keep things rolling forward, and so do I.”

A priority is “getting Willie out with his people”: not just putting him on tour, but booking special shows with artists who are his heirs and disciples. The concerts are logistically trickier than ever, what with the Covid precautions, but there is no thought of stopping. Younger musicians are eager — ecstatic, usually — to work with Nelson; he, as ever, is up for a picking party, and seems to enjoy the adulation. Sometimes these events take place, literally, in Nelson’s backyard. In 1985, a replica Old West town was built on Nelson’s property for the filming of the motion picture “Red Headed Stranger,” loosely inspired by his 1975 album; Nelson preserved the set and eventually installed an outdoor stage and sound system. This became the setting for occasional one-off concerts and special events, including the Luck Reunion, a festival held each March that draws thousands. There are also the birthdays, big occasions in Willie World. For Nelson’s 90th, next year, Rothbaum is planning the largest celebration yet, perhaps stretching over two days, maybe at the Hollywood Bowl. The guest performers, he says, will include “everyone you can think of.”

Another staple is Willie Nelson’s Fourth of July Picnic, a daylong concert, headlined by Nelson, that has been going since 1973. This year’s edition — the first since 2019, because of the pandemic — took place in Austin, at the 20,000 seat Q2 Stadium, home of the city’s Major League Soccer franchise. The supporting acts on the bill included Jason Isbell, Allison Russell and other young stars representing country music’s progressive wing. The paying audience was a typical Willie crowd: a cross section of humanity that seemed to represent every gradation on the local social spectrum, from hick to hipster. It was multigenerational, overwhelmingly but not entirely white and fashion-forward, in its way. There were cowboy hats and lots of American-flag-themed apparel, worn with greater and lesser degrees of irony. A sizable number of those in attendance were men and women in their 20s and 30s decked out in period-perfect redneck-hippie chic: big boots, big belt buckles, big beards, lots of hair. At a Willie Nelson concert, it’s always 1973 in spirit.

The man himself arrived onstage wearing his own version of patriotic garb: an oversize U.S. men’s soccer team jersey bearing the uniform number 420. Walking is difficult for Nelson, especially after his bout with Covid. He gets winded quickly; a few steps can leave him gasping. When he sings and plays, though, the signs of strain ease. “According to the doctors, singing is the best exercise for the lungs,” he says. “I think that’s true.”

At the picnic he was in robust voice, pushing out his songs with power, agility and flair. “Whiskey River” came first, of course, delivered in an insolent purr. Ballads unfurled in whispers and croons; livelier numbers were sung with snap, sometimes in a thick twang that Nelson seemed to have dragged out of the 1930s for the occasion. Seated to his left was the Particle Kid, Micah, who played rhythm guitar and got a star turn on a number whose lyrical hook — “If I die when I’m high, I’ll be halfway to heaven” — came from a quip by Nelson at the dominoes table during Covid lockdown. (When Micah told his dad that the phrase would make a great song, Nelson said: “You write it.”) Early in the set, the band cued up “On the Road Again,” and Beto O’Rourke dashed onstage with his own 11-year-old son to strum an acoustic and shout along.

Nelson played some fine guitar. During “Angel Flying Too Close to the Ground,” one of his most lustrous love songs, he took a solo that gusted between genres and across borders, flowing past in a blur of swinging syncopations and block chords and hard strumming that pulled in Gypsy jazz, Texas blues, mariachi, even flashes of surf rock. The performance brought whoops from the crowd and, when he reached Bar No. 16, drew an impressed head shake from Nelson, in the split second before he sang the next line — a fond farewell to a lover that, on this occasion, sounded more like a guitar hero urging himself on. “Fly on,” he sang. “Fly on past the speed of sound.”

Jody Rosen is a contributing writer for the magazine. His book “Two Wheels Good: The History and Mystery of the Bicycle” was published in April. Philip Montgomery is a photographer whose work examines the fractured state of America. His new monograph of photography, “American Mirror,” is a chronicle of the country’s historic struggles over the decades.