All Roads Lead to Willie Nelson: Rolling Stone's Definitive Profile of the Country Icon

LeAnn Mueller
Willie Nelson in Austin, Texas.

He is one of America's greatest songwriters, a hero from Texas to San Francisco, a hippie's hippie and a redneck's redneck. But does anyone really know Willie Nelson?

On a winding stretch of road 30 miles west of Austin, a couple of miles down from a hamburger shack and an auto-repair shop, there's an iron gate with the image of a cowboy silhouette. Type in a key code and ride up a steep, muddy incline surrounded by oaks, cedars and patchy grass. After a left turn at a barn, you will enter a ghost town: a white, wood-frame church, a jailhouse, a bank, a dance hall, a water tower and a saloon.

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Willie Nelson built Luck, Texas, on a corner of his 700-acre Hill Country property for his 1986 cowboy film Red Headed Stranger. Nelson wanted the movie to come out a decade earlier, at the same time as his classic album of the same name, but then Robert Redford, who was supposed to star in it, dropped out and Hollywood lost interest. Nelson, who had dreamed of owning an Old West town since he was a young Roy Rogers fan, pushed forward, despite the fact that he owed the government millions in taxes. He raised money with the help of investor friends. He cast his family and band in the movie, and enlisted University of Texas architecture students to build Luck. The movie originally called for the town to burn down, but Nelson had the ending changed.

"Oh, we never were going to tear it down," Nelson says in a low, husky twang as he drives a '94 Chevy through Luck on a clear, blue winter morning, before letting out a heavy cough. "We wanted to get all the movie money we could and then get them out of town!"

Today, Luck is one of the last standing Western film sets in the country, though "standing" may be an overstatement: The planking has fallen off a barn that houses a John Deere tractor, the imitation rock has almost completely peeled off the bank, and the post office has almost collapsed entirely. When the town's architect returned recently, he thought it needed to be bulldozed.

The ranch and surrounding area are known to locals as Willie World. Nelson also owns Pedernales Cut-N-Putt, a nine-hole course you can see from his house. Next to that is a recording studio, and condos for friends, family and longtime crew members. Poodie's Hilltop Roadhouse, a burger joint full of old Nelson posters and stage props, opened by his late stage manager Poodie Locke, is down the road on Highway 71; Nelson has been known to drop by for a surprise set. Drive to downtown Austin, and you'll find the new Willie Nelson statue on Willie Nelson Boulevard.

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With his youngest kids, Lukas and Micah, grown up and out of the house, Nelson spends his rare nontouring days driving around, listening to his Sirius XM station, Willie's Roadhouse, sometimes going off-roading and carving out paths. "I've thought I was going to die a few times with him in the truck," says his daughter Paula. "He's like a kid, doing the whole cowboys-and-Indians thing. It's his playground."

Today, Nelson is wearing a black hoodie, sunglasses and dirty New Balance sneakers, his semibraided hair tumbling out of a black baseball cap that says ZEKE'S SOCIAL CLUB. He steers his Chevy through the property with sharp, jagged turns, occasionally lighting up a burned-out joint in a cup holder. At one point, he stops the truck and singles out a stable: "I have a sick horse in there – we tried to isolate him from the herd a little bit," he says. "This is just old, rough country. A lot of room to drive around, a lot of privacy. I like Texas."

We pull up next to a rickety building in the center of town with a sign reading WORLD HEADQUARTERS LUCK, TEXAS. The musty wooden interior is packed with dominoes and poker and pool tables; Nelson frequently hosts Texas Hold 'Em games with a group of local musicians and businessmen. The walls are covered with novelty signs (OLD MUSICIANS NEVER DIE – THEY JUST DECOMPOSE; FOR A GOOD TIME CALL MATILDA: SHE GIVES DISCOUNTS). There's a WILLIE NELSON FOR PRESIDENT 2008 sign, posters advertising his famous Fourth of July picnics, which he's mostly hosted in Texas every year since 1973. Behind the bar are fan paintings and photos of Nelson with old friends – the late moonshiner Popcorn Sutton, Doug Sahm, singer-author Kinky Friedman – and a live shot of Johnny Cash. "He used to call me for jokes in the middle of the night – 'What's the latest?'" Nelson says.

He fires up his coffee maker, then reaches into a 1950s-style Hopalong Cassidy lunchbox packed with loose green pot and pulls out a tightly wrapped, torpedo­shaped joint. He takes a slow hit, holding it in as he looks at a mounted cow's skull near the fireplace. Next, he produces a vaporizer pen. "Do you ever smoke these?" he asks. "It's just pot – no smoke, no heat. You can smoke 'em on the plane!"

Nelson has been arrested at least four times on marijuana offenses. In Waco, Texas, in 1994, police found him asleep in his Mercedes on the side of the road, a joint on him, after a late poker game. In Louisiana in 2006, en route to Texas Gov. Ann Richards' funeral, Nelson's bus was pulled over and police seized 1.5 pounds of weed and two ounces of hallucinogenic mushrooms. Four years later, he was driving back from Thanksgiving in California when the border patrol arrested him in Sierra Blanca, Texas. ("He feels great – he said he lost six ounces!" joked his harmonica player Mickey Raphael at the time.) "They mostly want autographs now," Nelson says of the law. "They don't really bother me anymore for the weed, because you can bust me now and I'll pay my fine or go to jail, get out and burn one on the way home. They know they're not stopping me.

"Weed is good for you," he says. "Jesus said one time that it's not what you put in your mouth, it's what comes out of your mouth. I saw the other day that [medical] weed is legal in Israel – there's an old-folks home there, and all these old men were walking around with bongs and shit. Fuck! They got it figured out before we did!"

Abruptly, he changes the subject. "Wanna ride around a bit?"

Nelson turned 81 in April. He can be forgetful – in concert, he sometimes needs to look over at Raphael, a veteran of his band for more than 30 years, to see if they've played "Georgia on My Mind" or some other song yet ("But I think that's the dope more than anything," says Raphael). His hearing is shot, and he no longer signs as many autographs as he used to. But he still practices tae kwon do and sleeps on the Honeysuckle Rose, his 40-foot-long biodiesel-fueled tour bus, while the rest of the band check into hotels. At one point on the ranch, when he stops to show off his favorite paint horse, Billy Boy, he easily hoists himself up to the second­highest fence rung, balancing about four feet off the ground.

Willie spends about 150 days a year on the road – two weeks on, two weeks off – playing many of his 20 Number One country hits, plus the church and gospel songs of his youth and favorites by heroes like Bob Wills and Lefty Frizzell. Nelson is one of the last living links to the days when country pioneers like Hank Williams played barn dances and ruled the radio. He's an innovator who brought different strains of music, from gypsy jazz to hippie concept albums, to Nashville. He has sold more than 40 million albums and has put out 16 in the past decade alone, projects ranging from the Western swing of his youth to reggae and pop standards. His new album, Band of Brothers, which contains some of his most reflective songs in decades, is his first Number One album on the country charts in 28 years. It often sounds like a tour diary: "I've Got a Lot of Traveling to Do" is about turning to weed and the road to escape turmoil at home, and the soulful "I Thought I Left You" is about scanning a guest list for a former lover's name ("Why, in heaven's name, can't you just get lost?" he sings). "There's a little truth in all of them," he says.

Unlike fellow giants like Williams, Merle Haggard or Dolly Parton, who have plenty of obvious imitators, no one sounds like Nelson. He's an uncanny vocal phraser: "The three masters of rubato in our age are Frank Sinatra, Ray Charles and Willie Nelson," said the late producer Jerry Wexler. "The art of gliding over the meter and extending it until you think they're going to miss the next actual musical demarcation – but they always arrive there, at bar one. It's some kind of musical miracle."

In a time when America is more divided than ever, Nelson could be the one thing that everybody agrees on. "The Hells Angels love him, and so do grandmothers," says Raphael. But in private, he can seem introverted and given to long silences. He will often describe his life in brief, purely factual terms, saying things like, "Oh, why does a guy write? I don't know. You get an idea, and you sit down, and you write it." Over the course of 30 interviews with his friends, family and band members, a lot of the same words come up – generous, charismatic, loyal and, as Keith Richards has said, "a bit of a mystery." "He's really good at throwing out a one-liner that will get you off of what you're talking about," says Shooter Jennings, who has known Nelson since he was a kid tagging along on the Highwaymen tours with his father, Waylon. "You're like, 'Fuck, Willie, answer the question!' There's a lot of exterior there. That's why you'll never quite fully get that picture."

"You never get to know him like you should, but you know there's more there than what you're seeing," says Loretta Lynn. "I know there's more there because of how he writes. He can't fool me!"

"He's a hard man to know," Johnny Cash wrote in 1997. "He keeps his inner thoughts for himself and his songs. He just doesn't talk much at all, in fact. When he does, what he says is usually very perceptive and precise. . . . He has a beautiful sense of irony and a true appreciation for the absurd. I really like him."

'Say hi, Will," says his wife, Annie, turning her iPhone toward him. Inside their home, she's FaceTiming with some relatives in Italy. "How ya doin'?" Nelson says with a wave. They ask how his shoulder is feeling after a recent surgery. "Much better, thank you!"

Nelson has been recovering from a torn rotator cuff. "I couldn't play golf, and I could barely play guitar," he says. His friend George Clooney recommended a German treatment called Regenokine. "The doctor took some blood out and recharged it and made it with, like, 150 percent more healing power, then he stuck it back in there," he says. "It really works. I'm in great shape."

Nelson met Annie, 54, when she was working as a makeup artist on the set of his 1986 made-for-TV movie Stagecoach; she would become his fourth wife and longest marriage by far. "She's been with me through thick and thin – you can't ask for anything more than that!" he says.

Friends credit her with keeping Nelson healthy (they bike and swim at their second home in Maui, and he's cutting back on bacon). She also helped reduce his payroll. "There were a lot of people sponging off him, even though he didn't look at it that way," says Johnny Bush, Nelson's close friend and the writer of "Whiskey River." "They lived in the condos and at the world headquarters; there were trailers all over the place. And, of course, Willie wasn't going to tell them to leave."

Located up the hill, past a second gate, is Willie and Annie's Texas home, a modest, rustic log cabin modeled after turn-of-the-century smokehouses. The kitchen overlooks a giant barnlike living room, with tall ceilings and cedar beams. On a grand piano next to several guitars, there's a family portrait from the Nineties of the couple with Lukas and Micah, who frequently play music on tour with their dad. ("I've been hearing my licks come back better than they went out," says Nelson.) Next to a Hank Williams bobblehead is a minireplica of Nelson's Austin statue, a figure with a big grin, pigtails and hefty arms, clutching Trigger, his trademark acoustic. "What can you say?" Nelson says. "The sculptor may have exaggerated some points, but I'd say it's how I'd like to look."

He offers to show me his second­degree tae kwon do belt, and takes me into his bedroom, which has a plastic dresser full of socks and colorful Hawaiian shirts that he wears in Maui. "He's working on a third black belt, but he's kind of cheating," Annie says. He laughs. "I cheated on these!" he says. "If you want my honest opinion, I think it's kind of political. Every [martial arts] school wants theirs to be the best. I'd do the same thing if I could get someone with a name to come in."

We walk across the driveway to what Nelson calls Django's, a small log cabin where he spends most of his time. A baseball bat sits by the door; Al-Jazeera plays with the volume off on the flatscreen, while a liberal talk-radio show blares in the back of the room. There are shelves of books – books about the history of the Middle East, a book of sketches by Julian Schnabel and a Django Reinhardt songbook. Reinhardt has long been Nelson's favorite guitarist; he has been taking lessons lately, learning some of the jazz great's techniques from a teacher in Maui.

"Wanna see the arsenal?" Nelson says with a grin, using a loose piece of wood to pry open a wooden cabinet. "I couldn't get in here if I needed to," he says. He picks up a knife engraved with his face, an old sawed-off shotgun and a double-barreled rifle inscribed with the lyrics to "Red Headed Stranger" (a gift from Connie, his third wife), then takes out a .22-caliber rifle with a scope. "This one's pretty cool," he says, curiously peering down the barrel for several seconds. He has trouble fitting it back in the cabinet, so he forces it in, repeatedly banging it against the wood, with the barrel nearly touching his face, as I look on uneasily.

He settles into the couch, which is cluttered with free weights, some old black-and-white promo photos waiting to be signed and a Bible ("It puts some positive thoughts in your head when you might be thinking negative," he says). On the coffee table, there is a chessboard obscured under a CIA baseball cap, rolling papers, a grinder and an ashtray full of joints. "Might as well do some puffin'," he says.

As a kid growing up in Abbott, Texas, a hundred miles from here, Nelson would go down to the town's general store and play dominoes, the only kid in a group of fully grown farmers. "The older guys loved him," says his sister Bobbie, 83, who has toured with Nelson full time for the past four decades. "He'd hang out with the old guys and the young ones. People always just migrated toward him, the same way they do now."

But at home, he didn't have it easy. His parents, Ira and Myrle Nelson, got married when they were 16 and 15, respectively; Bobbie came a year after that, followed two years later by Willie. Six months after his birth, his parents split and his mother left for the West Coast, eventually settling in Washington. "Myrle was smart, flashy, full of energy . . . a dancer and a card dealer," Willie once wrote. "My mother could never have stuck it out as the wife of a Fort Worth mechanic on weekends." ("Willie is very much like our mother," says Bobbie.)

Ira left the kids with his parents, Will, a blacksmith, and Nancy, who picked cotton and gave singing and music-theory lessons at their house in exchange for food and secondhand clothes. By the time they were each six, Bobbie was playing piano and Willie was learning chords to spirituals like "The Great Speckled Bird" from his grandfather. Willie was already showing signs of talent; his first-grade teacher made a visit to their house after he aced a poetry assignment. "She said, 'You know, this is really unusual, his ability to write poems,'" says Bobbie.

That same year, the family was shaken again when Willie's grandfather died of pneumonia after suffering an allergic reaction to a medication. There was talk of splitting up the kids between their parents, or putting them up for adoption until their grandmother gained custody. In his 1988 autobiography, Nelson wrote, "I hadn't even had time to grieve for the loss of a mother and daddy, much less my grandfather. Our separation from Mother and Daddy seemed worse than a death because they were still out there in the world."

Willie spent his nights listening to his family's Philco radio – especially Nashville's Grand Ole Opry, discovering the fiddle-steeped country of Hank Snow, Roy Acuff's quavering heartbreak ballads and the wild, electric, jazz-flavored honky-tonk of Ernest Tubb and His Texas Troubadours. Willie also sat with his sister as she learned the complex pop songs of the time. "I'd be trying to figure out what the hell was going on in 'Stardust' and 'Moonlight in Vermont,'" he says. "All those great songs have fantastic chord changes in them."

By the time he was nine, Willie and Bobbie were performing at open-air summer church revivals. At one revival, Bobbie met an older guy named Bud Fletcher, who put together a Bob Wills-style band. They married when she was 16, and she and her brother joined the group. Willie ended up becoming the de facto bandleader, singing and playing lead guitar. He was 14 years old. "The girls loved him," says Bobbie. "They were like a fan club of his that just was always there."

After turning 18, Nelson spent nine months in the Air Force during the Korean War before being honorably discharged for a bad back. He considered a career in business, briefly attending Waco's Baylor University ("I majored in dominoes"), before returning to the Texas honky-tonk circuit. At one gig, he met Martha Matthews, a pretty 16-year-old Cherokee brunette. They eloped three months later. The relationship produced three kids and "enough heartbreak to inspire most of the songs that got him elected to the Songwriter's Hall of Fame," their daughter Susie Nelson wrote in her book, Heart Worn Memories.

The family spent the Fifties traveling the country, looking for work. In Eugene, Oregon, Nelson was a plumber's assistant; in Fort Worth, Texas, he sold vacuum cleaners and encyclopedias door to door. He could be loose with the facts; he says he used the "negative approach" (opening line: "I'm not a salesman, and I can't sell you anything, so don't try to buy these books. . . . "). "You got your little story you tell, and you get your feet in the door and try to sell a set of books that costs more than their furniture," Nelson says. "I took a little pride in the challenge of knocking on the door and being able to talk my way into the house."

In San Antonio, he talked his way into a $40-a-week morning-disc-jockey job by saying he knew how to run the control board. That led to a position at Fort Worth's KCNC in 1954, where he capitalized on his position by bringing his guitar to work and playing his music between records by Eddy Arnold, Kitty Wells and other stars. "I was promoting my shows on the radio," he says, and then breaks into character: "'I'll be playing Gray's Bar tonight in Fort Worth – y'all come over!' It helped both areas, you know?"

(At that point, Nelson had not yet developed a taste for weed. Johnny Bush remembers: "We were all passing it around before a gig. Willie drove up, and I said, 'Hey, you want some of this?' And he said, 'No. That shit gives me a headache.' Can you believe that?")

Nelson spent two years on the Houston nightclub circuit, where he managed to score a Top 10 country hit when the honky­tonk singer Claude Gray covered Nelson's gospel song "Family Bible." (Nelson famously sold it to Gray for $100.) Then in 1960, he drove his Buick to Nashville, home of the Opry and several newly opened record labels. "I thought I had some good songs," he says, "and I knew Nashville was the store you went to sell them." The 27-year-old Nelson moved his family into a trailer park and used his Texas-nightclub connections to get in the door at Tootsie's Orchid Lounge, a hangout for the city's top musicians. He became a regular at the back room's exclusive guitar jams, showing off songs like "Night Life," "Crazy" and "Funny How Time Slips Away" for pro songwriters including Harlan Howard, Roger Miller and Hank Cochran, who quickly helped him get hired at his publishing company, Pamper Music. At Pamper, Nelson would clock in weekday mornings and write songs like the offbeat ballad "Hello Walls," which became a Number One country hit for Faron Young in the spring of 1961. Ray Price, who was one of the biggest stars in Nashville at the time and a co-owner of Pamper, recorded "Night Life" – Nelson's diary of seedy bars and heartbreak – which became the title track of Price's Number One country album. "I thought it was more of a blues song, but it turned out great," Price said. Nelson also played bass in Price's band the Cherokee Cowboys. The two stayed close; when I spoke to Price two weeks before his death from pancreatic cancer, he said he and Nelson had spoken eight times that week. "We're sort of like brothers," Price said. "I lived with Hank Williams the last year of his life, and he was just like Willie. His secret was he could walk out onstage and just be himself, and that's what it's all about."

As Nelson's career heated up, so did tensions at home, thanks in part to his heavy drinking and infidelities. "Things started to fall apart for real the minute we hit Nashville," his daughter Susie wrote. Once, after Nelson came home and passed out, Martha tied him with jump-ropes and beat him with a broom, then left with the kids for several days. Another time, she charged at him with a butcher knife. "The next day he was gone again," Susie wrote. "That's Dad's way. When things get too hot, he just disappears. He doesn't like confrontations." In 1963, Nelson married singer Shirley Collie, whom he began dating while still married to Martha. "A minor detail he forgot to take care of," Bush says, laughing.

Nelson's biggest break came one night at Tootsie's when he played a demo of "Crazy" for Charlie Dick, the husband of Patsy Cline, the Opry's biggest star at the time. Dick insisted they drive home and wake up Cline, where Nelson sang it to her live in her living room. She cut it one week later. "I'd sang the song a million times, but never like that," says Nelson one night on his bus through a haze of smoke, breaking into the rise-and-fall melody. It would become a Top 10 pop hit, earning Nelson six figures that year. "That's a pop song. There's nothing country about it – unless Patsy Cline sings it." (It would be one of Cline's last hits; she died in a plane crash in Tennessee in 1963.)

"When I went to Nashville, all the serious songwriters idolized Willie," says Kris Kristofferson. "He played guitar like Segovia and phrased absolutely unlike anybody, like a jazz singer, just like he does today. He wasn't well-known outside of that, but he was the hero of all the serious people."

Nelson became a full-time Opry member in 1964, performing the required 26 nights per year. "He was stylish," says Loretta Lynn. "He was working in suits. His hair was cut every little bit, he had brass eyes, and his hair was the same color. He was really handsome!"

But by the end of 1968, Nelson was in a professional rut. He had released a dozen records on RCA, cranked out with session players and strings, but he'd yet to have a major hit as a performer. He suspected the label was just keeping him under contract to give his best songs to bigger names. "At that point, you wouldn't have put your money on Willie," says Friedman. "Nashville got the idea that he was offbeat."

On the night before Christmas Eve 1969, he was at a party when he received an alarming call: His house was on fire. (By this time, he had discovered pot; he ran inside to rescue two pounds of weed.) He took it as a sign to move back to Texas, where Bobbie was raising a family and playing her brother's songs at nightclubs. He moved into an abandoned country club in Bandera, between San Antonio and Austin, the latter of which had grown into a progressive town with 35,000 college kids. Nelson formed his Family Band, a mix of young longhaired rockers – including bassist Bee Spears and harmonica player Raphael – and older players like Bobbie on piano and drummer Paul English, a former pimp and gang leader who dressed liked the devil in all black with a cape and a goatee. Nelson had known English since his days in Fort Worth in 1956. "If I hadn't gone with Willie, I would be in the penitentiary or dead," English says. "I was running girls and playing music at the same time."

The country-folk directions of Bob Dylan, the Band and the Grateful Dead had influenced the jacked-up honky-tonk sounds of Jerry Jeff Walker, Doug Sahm and Asleep at the Wheel. Nelson was ready to take it a step further. He asked the band to change its image – "I bought jeans and a cowboy hat," says Bobbie – while he grew his hair out and switched over to Trigger, the nylon-string acoustic he bought sight unseen for $750 from a Nashville guitar dealer. He started embracing his swing and jazz roots, trading solos with Raphael's harp and Bobbie's gospel-steeped piano. "We were just playing the same music we'd played since forever," says Bobbie. "It was just a different audience."

The band started filling up hippie clubs like Austin's Armadillo World Headquarters. They also played shows on what Raphael calls Texas' "blood-and-bucket" circuit, which weren't as welcoming. "I'd wait in my car until Paul got there, or the rest of the guys got there," says Raphael. "I was a Jewish kid with an Afro – they didn't know what the fuck I was. They thought I was Hispanic."

Spears, a shaggy 19-year-old at the time, had it the worst. "When Bee would walk to the bathroom in some of these joints during intermissions, the rednecks would stick their legs out and try to trip him," remembers English. "I always walked with one of them to the bathroom."

The hippie and redneck worlds famously converged at 1972's Dripping Springs Reunion, country music's Woodstock moment. The bill combined new acts such as Walker, Waylon Jennings and Kristofferson with vets like Bill Monroe and Ernest Tubb. Drawing only 18,000 people over three days, it was a financial disaster, but Nelson used the same location the next year to stage the similar Willie Nelson's Fourth of July Picnic. It drew 40,000, establishing him as the pre-eminent leader of a new, slightly dangerous music scene. "Backstage it was pot, whiskey, pills and some cocaine," Jennings said. "The audience was as twisted as we were: all day and all night drinking hot beer."

"The French have a good word: laissez faire," says Jimmy Buffett, who played his first of many picnics in 1974. "Anything went. There was nothing like those first ones. There were a lot of hot-looking college girls – I always liked that crowd better than the bikers."

In the early Seventies, Jerry Wexler signed Nelson to Atlantic, finally allowing Nelson to use his own band in the studio rather than Nashville session players. It kicked off an incredible run, including 1974's Phases and Stages, a concept record covering both the male and female sides of a failed marriage. Nelson had recently divorced his second wife, Shirley, after she had opened a hospital bill for a child Nelson had conceived with his future wife, Connie. ("I was going through a lot of shit," Nelson says.)

In 1975, he recorded a set of songs centered on the old murder ballad "Red Headed Stranger," the story of a preacher on the run after killing his wife and her lover. Between the album's spare, subtle instrumentation – much of the disc is just Nelson and Bobbie playing – and the Old West-style portrait on the cover, it felt like Nelson was stepping into the boots of a John Ford character. Nelson knew that it would be a hard sell to his new label, Columbia, so his manager brought Jennings into a meeting; when one exec said the album sounded like a demo and suggested sweetening it with some Nashville strings, Jennings called him a "tone-deaf, tin-eared son of a bitch." The label relented, and Red Headed Stranger went double platinum.

Suddenly, Nelson and his friends ruled the radio with songs like "Blue Eyes Crying in the Rain," and his Jennings duet "Good Hearted Woman," from 1976's Wanted! The Outlaws. On some level, Nelson knew that he was playing a part. "All of a sudden, we were outlaws," says Nelson. "I thought it was the funniest thing in the world. And I tried not to disappoint 'em!"

"I remember in Corpus Christi one night when everybody in the band had eaten some mushrooms," says Raphael, describing a gig in the mid-Seventies. "I said, 'I can't wait till Willie gets here – there will be some semblance of normalcy.' And he shows up, and he'd taken some acid, tripping his ass off. And he says, 'I hope you guys can hold it together.'"

"Everyone carried guns, everybody did drugs, everybody drank," says Gator Moore, Nelson's longtime bus driver. Some of the wildest parties happened during Nelson's residencies at Vegas' Golden Nugget. "We'd stay up for days," says English. "Willie's generosity with paying all the hotel bills led to some drinking excesses with the crew." Moore says, "At one point, somebody figured out we were spending $80,000 a year on beer" – about a third of a million dollars today.

The hiring process for crew members was loose. After the band met the Hells Angels during a highway traffic jam in the late Seventies, Nelson brought on the motorcycle club to promote some California gigs; some bikers got full-time work out of it. "He just got used to seeing my face," says L.G., a longtime Hells Angel who has been Nelson's security guard since 1978. "One day, he told Paul [English] to give me a raise. Paul said, 'Well, he doesn't work for us.' Willie said, 'Give him one anyway!' And that's how I got hired."

Raphael and other band members developed serious cocaine habits. "We were all playing too fast, too much," Raphael says. "Willie would play something, and we'd all answer him." The musical chaos prompted Nelson to institute a rare rule on the road: "You're wired, you're fired." ("Crank was known as the loophole," says bus driver Moore, who once drove 96 straight hours on the drug in the Eighties. "That was OK.")

English calls Nelson the "calm center" of the madness during this time, but even he could lose his cool: "In Dallas, he had taken some THC or PCP or something, and he quit playing in the middle of the show and threw his guitar at Poodie," English says. "I had to sit at the foot of his bed all night to make sure he didn't get up and go on a tear."

What was perhaps Nelson's most famous outlaw moment came in 1980. After being arrested for weed possession at a Bahamas airport, he flew straight to D.C., staying in the Lincoln Bedroom at the invitation of a friend, President Jimmy Carter. "There I was . . . on bond, deported from the Bahamas," he later wrote. "A few hours later, I was on the White House roof smoking dope." (Today Nelson is more cagey about the incident: "Oh, that might be true," he says. "I forget.")

By the mid-Eighties, Nelson had scored 20 country hits, won five Grammys and starred in six films. He was pulling in more than $14 million a year from touring, and traveling on a seven-seat private Learjet called AirWillie. In 1985, he teamed up with Jennings, Cash and Kristofferson for the critically acclaimed Highwayman album, which the foursome followed up with an arena tour.

Cash and Kristofferson grumbled on the road that Nelson got to play one more song than the other bandmates – a reflection of the fact that Nelson's career had overshadowed his old peers. (Cash hadn't had a Top 10 hit in almost a decade, Kristofferson hadn't recovered from his flop Heaven's Gate, and Jennings had been in serious debt, playing the state-fair circuit.) Jennings and Nelson always had a brotherly but competitive relationship. "I think Waylon was jealous of Willie," says Haggard. Jennings took a shot at Nelson with his 1975 song "Bob Wills Is Still the King" and suspected that Nelson treated him unfairly when it came to money. ("I've had to start my life over several times because of him," Jennings wrote in 1996.) At one point in the Nineties, Jennings was playing with just a backing track and ripping into Nelson onstage. "He dissed him pretty bad," says Shooter, "saying Willie had these guys working for him who were shysters." Shooter says he went to go see Nelson backstage at a show shortly before his father's death. "He asked me, 'How's he doing?' I said, 'He's hanging in there.' And he said, 'Well, tell him to come out and do some shows with me. I'll write him a bad check.'"

On November 9th, 1990, federal agents descended on Nelson's Texas properties, unloading boxes of master tapes, touring equipment, gold and platinum records, and clothes. "They came in and took every damn thing in that place that wasn't nailed down," says Bush. IRS agents served Nelson with a $16.7 million tax debt.

Nelson had seen it coming; two weeks earlier, he had his daughter Lana send Trigger to Maui. The trouble had begun 10 years before, when the IRS demanded $2 million in back taxes for Nelson's haphazardly managed mid-Seventies earnings; investigators were especially suspicious of the low profits reported from his Fourth of July picnics.

Despite all his success, Nelson had dug himself into a hole in the Eighties by investing in First Western tax shelters, saying he was following the advice of his Price Waterhouse accountants. "I remember on his bus he told me they were going to borrow $6 million to go into cattle futures," says Bush. "I said, 'Willie, you scare the shit out of me when you talk like that.' He said, 'It's just money.'" Nelson and his financial manager ended up losing $2 million. In 1988, he was served a notice of deficiency for unpaid taxes from 1980 to 1982 for more than $5 million. Nelson's lawyer negotiated a payment plan, but Nelson missed the deadline. "He probably didn't have $30,000," Lana told Texas Monthly, estimating her dad kept only 10 percent of his annual income, giving the rest away. "People just hung on him," says Haggard.

Almost everyone close to Nelson has a story of his generosity. When English lost his first wife, Nelson invited the drummer to Mexico to hang out with Dylan. Late in Price's career, Nelson called Price on his birthday: "Willie said, 'We're waiting on you,'" Price recalled. "I flew in, and we cut a whole album. That's the kind of cat he is."

Nelson's properties and possessions were auctioned off. The University of Texas football coach Darrell Royal bought the golf course and studio, and a lawyer for the American Agriculture Movement bought the ranch as a thank-you for Nelson's efforts with Farm Aid. "They bought the ranch and saved it for me, gave it back to me," Nelson says. "I got a lot of friends."

Nelson launched a $45 million lawsuit against Price Waterhouse, which was settled out of court. He sold his entire Willie Nelson Music publishing company for only $2.3 million and cut a deal with the IRS to raise money through touring. Part of the deal was the album Who'll Buy My Memories? (The I.R.S. Tapes), a collection pulled from the 35 years' worth of seized master tapes and sold for $19.95 via infomercial. (It didn't sell a fraction of what it needed to – in part because Nelson wore the wrong phone-order number on his T-shirt during a broadcast.) "It was funny, you know," Nelson says on his bus. "We were afraid they were gonna come take the door receipts for taxes, so I quit playing for a while until we made the deal. I came out with enough to pay off the IRS, and I got even with those guys. But it was a long 16 years."

The IRS scandal hasn't stopped Nelson from handing out financial advice to his friends: "I had blown hundreds of thousands of dollars in Vegas," says Friedman of a recent conversation. "And Willie told me, 'What I think you ought to do is mortgage your house, sell everything you have and play the slots. It's what you like to do. It's what you want to do.' That was his advice."

In the midst of Nelson's tax problems, true tragedy struck. His 33-year-old son, Billy, had struggled to find his place in the world, becoming a heavy drinker, with four DUI arrests. Willie had given him jobs on his property, in the studio and on film projects. "Willie felt real bad about the fact that when Billy was growing up, he wasn't there at all," says Ray Benson of Asleep at the Wheel. "He tried to make it up to Billy in so many ways, and it was not going to help." Billy was found on Christmas Day 1991, after hanging himself in his Tennessee home. "I was around then, and he never mentioned it," says Haggard. "You will never see that side of him." The photos on the pinup board behind Nelson's booth on his bus constantly change, but one stays the same: Billy, in his twenties, smiling on a horse.

Six days after Billy's death, Nelson was onstage with his band at his newly leased theater in Branson, Missouri – the Ozark tourist trap that was also home to the floundering careers of Cash, Haggard and Roger Miller in the early Nineties. Nelson and his band cut their salaries in half and played two shows a day, five days a week, with autograph sessions after every show. "He was a prisoner," says Benson. Adds English, "The crowds were very old, and they would bus them in. We saw one guy go to sleep in the front row."

Nelson recorded some of his rawest music around this time. He sounds shattered on 1996's acoustic Spirit, exploring loss and faith, accompanied by little more than sister Bobbie's piano. "We were going through a period in our lives where we wanted to feel the spirit," says Bobbie. "When we play, it's a little bit like going in for Communion and praying."

Many things haven't changed about Nelson's touring operation since the Seventies. At 81, English still handles payroll and bills for the traveling group of 19; like the old days, he still deals heavily in cash. English had a stroke in 2010, but he was back on the road almost immediately, even if he played only three songs a night. "It's hard to give up, it really is," he says, sitting in his office in the back of the band's bus. Tonight, at Gruene Hall, Texas' oldest dance hall, near San Antonio, English will grin through "Me & Paul," Nelson's story of their wild past, playing a snare drum with several $100 bills spilling out of the pockets of his Western shirt. The band is getting paid $75,000. "That's pretty good for this run," he says.

Paul's brother Billy English, who has played percussion in the band since the mid-Eighties, says he generally only sees Nelson onstage. "He doesn't like confrontation, so we don't bother him with stuff that happens out here, whether it's financial or nothing like that," says Billy. "But he still is very generous to us. He pays us very well. As much as he could possibly afford to, maybe more."

Nelson's band has lost some key members in the past five years, people who can't be easily replaced. Bee Spears died after collapsing outside his home at age 62 in 2011; guitarist Jody Payne, Nelson's grizzled sideman of 35 years, died in an Alabama hospital of heart problems. "Those guys had mental telepathy perfected," Nelson says. "I'd play a note or two, and they'd be right there. It takes a little bit longer with the new guys, but sister Bobbie is right there all the time."

Parts of Nelson's set list haven't changed for 40 years. He always opens with "Whiskey River," then goes into a medley of "Funny How Time Slips Away"/"Crazy"/"Night Life," just as he did on Live at the Texas Opry House in 1974. But he still finds ways to be creative. "Every night is a gamble, like walking a high wire without a net," he says one night in New York. He recently pulled out Reinhardt's "Vous et Moi" when he missed a note and lost his place. "It completely fell apart," says Nelson. Other times, he'll play "stump the band": "I'll start something and start something else," he says with a grin on his bus in New York. "But usually, it's me doing the fuckup and they're trying to catch up."

Off the road, Nelson splits his time between Texas and Maui, which he calls his "hospital zone." In Hawaii, after swimming and playing golf all day, he'll head to his clubhouse (also called Django's). Neighbors including Kristofferson, Woody Harrelson and Owen Wilson stop by for chess, poker and dominoes. "He's definitely the number-one dominoes player," says Wilson, who says the only time he's ever seen Nelson mad was when he asked him, repeatedly, why the spare dominoes go on the right side of the table. ("Because that's the goddamn rule!" Nelson screamed.)

"He kicks our ass," says Harrelson. "He stays up all night partying and gambling. I mean, he's got reserves behind reserves of energy. It's just shocking. And he's one of the funniest people alive."

Once, after a compliment, Nelson asked Harrelson, "Where's the box?" "What box?" Harrelson replied. "The box you just stood on to kiss my ass," said Nelson. Harrelson regularly writes down his favorite Nelson one-liners: "If I hurt your feelings, I'm sorry. But if I made you mad, fuck you." "One thing I hate is a sink full of dishes and no place to piss." "If I can't be your number one, then number two on you."

"There's some freakin' nut cases that come by his house on the regular," Harrelson says. "These are people I wouldn't have over a second time. And he just treats them great, and he'll give jobs to people who don't have money – you know, 'Sweep this up.' He leads with his heart, and it's a beautiful thing to behold."

The Texas flag is hanging above the stage, the red bandannas are laid out across the amps, ready for Nelson to throw them into the crowd, as the Honeysuckle Rose winds past a golf course at Harrah's casino in Council Bluffs, Iowa. L.G., who is now 68 years old with a gray ponytail, tells a brunette to move her sedan, double­parked in a reserved spot by the stage entrance, so that the bus can edge in. "Someone constantly wants to see him, somebody wants this, somebody wants that," says L.G. "So we figured if he comes in an hour before the show, he doesn't have to deal with all that."

Two nights earlier, Bobbie had an alarming blood-pressure scare in Oklahoma City. They canceled the show, and she and Nelson went home to Austin, where she checked into a hospital; the rest of the touring crew went ahead to Iowa and waited to hear if the tour was canceled. "He called me to see if he could try and finish the tour," Bobbie says. "I said, 'Yes, I want to go, too.' I thought that was exactly what we should do, is to go get on the bus. We could not miss playing for those people that were waiting to hear us."

During the 850-mile drive from Austin, Nelson and his sister watched The Colbert Report and The Daily Show, but mostly rested. They arrive just in time for an ABC News interview about Band of Brothers, which just hit Number One. "It's as good as it gets," says Nelson, emerging from his bedroom, cleanshaven, hair braided and clutching a beige Stetson. "The other night in Arkansas was the best show we've ever done," he says. Really, the best ever? "Well, short-term memory has its benefits," he says with a smile.

We talk current events. He had read New York Times columnist Maureen Dowd's recent piece about eating a cannabis candy bar and needing to lie down, terrified and motionless, for eight hours. "Maybe she'll read the label now!" he says, laughing, adding she's welcome to get high on the bus "anytime." He's also been closely following the story of the 60,000 Central American children who have crossed the Texas border in the past year and are now sleeping in holding cells. "The only thing we can do is take care of those kids, whatever it takes," he says. "Take them in, give them some medical attention. I'm sure there are homes all over the country that would be glad to take one or two kids."

In June, heavy winds ripped through Luck, destroying the bank and the post office and leaving the headquarters on the verge of collapse. "It got a bad hit. We'll have to tear it down and build it back," Nelson says matter-of-factly. "We'll build it back stronger."

Nelson is already looking ahead. He just finished another new album, December Day, cut with members of his touring band, including Spears before he passed away. "Would you like to hear it?" he asks. He opens up his MacBook and plays several solo acoustic songs, such as the stark Sixties ballad "Permanently Lonely." "I think it'll be the perfect thing to follow up Band of Brothers," he says. Nelson says he isn't planning on promoting it heavily on the road, though. "I'm cutting back a little bit," he says. "I think after this tour, I'm working fewer dates. I'm just tired. I want to hang out with Woody and Owen more."

Friends close to Nelson say he was deeply affected by the loss of Ray Price, who died at 87 in December. "He was my best friend," says Nelson. He pauses for a moment as his brown eyes cloud up. "He was kind of everything in my career. All the way back to when I first started writing songs for him, playing bass for him, he just kind of took me in and raised me."

Months earlier, sitting in his truck at his ranch, I asked Nelson how he manages these losses. "Oh, we're all going to die," he said. "Who was it, Seneca, the thinker, that said you should look at death and comedy with the same expression of countenance? You can't be afraid of living or dying. You live and you die, that's just what happens, so you can't be afraid of either."

Nelson imagines a future when he plays only Texas – go to Fort Worth, come back, go to Houston, come back. "I don't have any burning desires to do anything – that's why it's dangerous," he said. "I have to keep booking myself or else I'll just do nothing."

He got a text from Annie. The bus was waiting down the hill. He needed to head to a local movie theater to make an appearance at a screening for a low-budget Austin holiday film in which he plays a Father Christmas-like figure.

"I just like to keep moving," he said. "I could lie down and go to sleep and not go anywhere or do anything, real easy. I'm lazy. I have to make myself do it. But once I do, I'm happy."

From The Archives Issue 1216: August 28, 2014

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