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At 85, Willie Nelson Knows the Secret to a Life Well Lived

For 60 years, country music outlaw has set the bar for being true to yourself

Willie Nelson turned 85 in April, and though he still tours, drinks, vapes, writes and golfs, he’s smart enough to know where he is — on the flip side, the back nine. It gives him freedom; he’s down to essential things now, with time for only what he truly loves. Like his wife and children. Like his famous guitar, Trigger, the one with the hole worn through the top from strumming. Like Frank Sinatra and country music. 

Willie’s taught us so much — how to be an honest outlaw, how to properly wear a bandanna, how to listen and how to be cool. Now just one lesson remains: how to remain yourself while getting old. “I don’t think that my attitude has changed,” he told me. “I’m still doing what I want to do, and I suggest everybody do the same thing.”

I could try to sell you on the importance of Willie Nelson, but why? He notched his first hit as a songwriter in 1960 with a tune called “Family Bible.” In the decades that have followed, he’s performed on 24 platinum or gold albums and composed dozens of pop and country hits, including iconic, timeless numbers such as “On the Road Again” and “Me and Paul,” about wild times on tour with his drummer, Paul English. He’s appeared in more than 40 movies and headlined thousands of sold-out concerts. He smoked a joint on the White House roof during the Carter administration in 1977; organized Farm Aid, the annual benefit for American family farmers, in 1985; and made more than a few men reconsider the practicability of braids. He has his own satellite radio station, Willie’s Roadhouse, which is partly programmed by his daughter Paula. He has his own brand of weed, Willie’s Reserve, a bespoke variety that’s been well funded by venture capitalists. Some of the labels in that line carry Willie’s sleepy-eyed countenance, making him a kind of Captain Morgan for the bloodshot set. He was at the center of a group of run-around country music pals — with Waylon Jennings, Johnny Cash and Kris Kristofferson — who played together as the Highwaymen. As one of two survivors of that crew, Willie stands as a last living link between Hank Williams, the Babe Ruth of honky-tonk, and Blake Shelton, a country star of the moment.

Of course, there have been hard times, for this is country music: drug busts and failed marriages. The first marriage, which lasted 10 years, gave Willie a lot of the heartbreak material that still turns up in his sad songs. And in 1990, after Willie followed some disastrous financial advice, the IRS seized about everything he had — saying he owed $32 million in back taxes — with the exception of his guitar and his voice, which he used to climb back out of the hole.

Wille Nelson sitting on a stool playing a guitar on stage. Box reads

David McClister

These days, he seems more joyful than ever, as satisfied as any country singer who’s lived past 30. His album count is well over 100, and his latest, Last Man Standing, features all new, original songs. He’s at work on a collection of Sinatra tunes, including “My Way.” But Willie does not like to talk about his achievements or place in history or how it will all be tallied when he’s gone. Sing about it, write about it, sure — his current live show includes “Still Not Dead” and “Roll Me Up and Smoke Me When I Die” — but discussing his legacy with a reporter is the worst kind of bad luck. He wants to talk about his life instead. He grew up in Abbott, Texas, a blink-and-you’ll-miss-it spot 70 miles outside Dallas. “They say the population never changes,” he told me. “Every time a baby’s born, a man leaves town.” His parents divorced when he was an infant, leaving Willie and his older sister, Bobbie, who gives his band its piano distinction — her instrument sounds as rickety as a piano in a saloon in Deadwood, S.D., circa 1885 — to be raised by their devoted grandparents. Comfort came via radio, old-time music wending through a Texas night. It suggested another kind of existence. 

At some point, Willie picked up a guitar. “I started when I was 5 or 6,” he told me. “I had one of those old Sears & Roebuck guitars with the strings high off the neck — your fingers literally would bleed. When they healed up, though, they were pretty tough.” He was soon singing and playing at churches and in town halls, his sister hammering away at his side. Other things happened: He joined the Air Force, worked as a door-to-door vacuum and encyclopedia salesman, and as a disc jockey. And wrote. Those first songs came under the influence of country legends. “Bob Wills era,” he said. “Spade Cooley. Tex Williams. All those great Western swing bands.”

Flat broke, Willie headed to Nashville, Tenn., the mecca of country music. That was 1960. He worked his way into the late-night lineup at Tootsie’s Orchid Lounge, which was across the alley from the Grand Ole Opry. Singers and songwriters partied at Tootsie’s from can till can’t. It’s where Willie debuted the songs — many now considered classics — that would become career-defining hits for other artists: “Hello Walls,” “Night Life,” “Funny How Time Slips Away.” One night he played a demo for Charlie Dick, a manager who happened to be married to Patsy Cline. Dick took Willie home, woke Cline and made Willie play her the demo tape. It was called “Crazy,” and it went Top 10 for Cline in 1961. Released before she died, it’s forever associated with the sadly beautiful mood of that short life. 

Willie had a record contract of his own, but his voice was different from what you usually heard on the country charts. It had that old Western thing, the twang, but it was sophisticated, too, all about emphasizing certain words and drawing out certain syllables. It was only when he moved back to Texas that he found his audience and became not just a star, but the biggest star in country music. The rest followed as in a dream — surprising yet inevitable. Records and movies, sold-out stadiums, tours. He let his hair grow, braids thrown back, took up marijuana as a way to settle his mood. Before dope, he’s said, he was angry a lot of the time. His face became famous in the way of a few other faces: John Wayne, Dolly Parton, Louis Armstrong. It represented not just a catalog of songs but a way of being in the world.

By the mid-1970s, he’d become that rarest of stars — an icon admired by even bigger icons. Bob Dylan recalls meeting Willie and his sidekick, English, at film director Sam Peckinpah’s house in Mexico in 1972. Willie and English “had driven down there in an old blue Mercedes 300 from Texas,” Dylan said. “We were sitting around in the living room, and Willie played some of his songs: ‘Night Life,’ ‘Hello Walls,’ ‘Crazy’ — all the great ones. I thought these were the most perfect songs that ever had a right to be written. I thought he was a genius then, and I think the same thing now.” 

I’ve listened to Willie Nelson all my life but fell in love with him in 1992. It happened in a bar in New York City called the Lion’s Head. One night, I happened to play his version of “Blue Eyes Crying in the Rain” on the jukebox. It’s a Fred Rose song, unspeakably sad, the story of a man mourning his wife and looking forward to meeting her in the next world. It carries echoes of the oldest American music. It’s an intimate hillbilly whine. Willie recorded it in 1975 for Red Headed Stranger, one of his first million-selling albums. It was among the breakthrough songs that took Willie from Nashville 1960 into the 1970s and beyond. He found his mature style on that song, realized that he could sing anything and make it new. I’d get drunk on the sort of drinks I figured Willie would order — tequila, beer — line up my quarters and play the song till the men at the rail begged me to stop. When you are 22 and lonely and far from home, you feel sorry for yourself in a way that is the essence of country music. His voice was humorous and sad and full of wisdom; I knew he’d understand everything. If I ever did get to meet Willie Nelson, I promised myself I’d ask him the secret of life.

Willie Nelson on stage performing with two of his children.

Janis Tillerson

The two youngest of Willie’s children, Micah, center, and Lukas, often perform with their dad.

I caught up with Willie on his tour bus 26 years later; it was in March, just before he went onstage at the Peace Center in Greenville, S.C. He was sitting at a small table in back. Looking over his shoulder was Annie, his fourth wife. A makeup artist who met her husband in 1986 on the set of his made-for-TV movie Stagecoach, Ann Marie D’Angelo has been by Willie’s side through his health scares, pot busts, tax problems — “through thick and thin,” he’s said. “You can’t ask for anything more than that!” She travels with him and looks after his health — got him into bicycling, organic foods and living as if he intends to last. “Annie and I have been married since 1991 and found a way to make it work,” Willie has said. They have two adult children, Lukas and Micah, good musicians who often perform with Willie and their Aunt Bobbie. Willie was married three times before and had five other kids. In 1991, his oldest son, Billy, died at age 33. It’s something Willie never talks about, but it can be heard between every note of his most wrenching songs.

When we met, Willie was wearing a black T-shirt and jeans. He’s always looked like Willie — it’s one of those rare things you can count on — but looks the most like Willie now, in the middle of his ninth decade. His eyes are mischievous. One braid hangs down his chest; the other, down his back. His smile is wry, amused. When he laughs, he tilts back his head and stares at the ceiling. In short, Willie Nelson looks exactly like you want Willie Nelson to look.

I’d heard he does not like to talk, that he lets silence fill the gap between him and his interrogator, but I did not find that. Then again, I didn’t ask him dicey questions about politics or marriages. Instead, we talked about what he has loved: Hank Williams and Django Reinhardt, the highway when you are sober and the highway when you are drunk, the last bit of beer in the bottle, the last hour of night in the day. 

Like Elvis, for example: “Did you know him?” 

“Yeah, I met him a couple of times,” Willie said. “He did ‘Always on My Mind’ and ‘Night Life.’ ”

“Why did he have such a hard time?” I asked, meaning the isolation and the jumpsuits, the Memphis Mafia, pill addiction and early death.

“Well, it ain’t easy,” Willie said. “Once you think it’s easy, you’re in trouble.” To achieve fame, he added, “you’ve got to want it. And then, when you get it, you’ve got to still want it. A lot of people, when they get it, say: ‘Wait a minute, this is too much.’ ”

Willie once said that singing the same sad songs night after night had, in the past, driven him to the bottle. Why, though? I’ve always found that listening to sad music made me feel better. 

Wille Nelson with a hat on and smiling

LeAnn Mueller

“Whenever me or George Jones or whoever is singing those sad songs, there’s people out there that can relate to it, and that’s good,” he told me. “The problem can be that getting in that emotional state to sing that sad song to make all those people happy, you’re really putting yourself in a negative situation where you want to drink more.”

Whenever I asked about influences, the conversation turned to Hank Williams. Willie looked over my head when talking about Hank, as if he could see him out there, in his sequined Nudie (Cohn) suit. “He was an incredible writer, sang with so much feeling,” Willie said. “He was a sick man from the time he was born till he died, a sick man. He had a bad back and was always on some kind of pain medications or alcohol or whatever it took to get him up to the show. And he had a hard life. Died at 29. But nobody wrote better songs than Hank. It was the simplicity, melody and a line anybody could understand.”

This led to talk of the old days, when the highway turned to dirt as soon as you left town.

“What was Nashville like in the ’60s?” I asked.

“Nashville’s always Nashville,” he said. “It’s where you take your goods to sell, and if you’ve got anything good, cool. If you don’t, they’ll let you know pretty quick. One thing about having a country hit is you can live on it forever. There are people who always like Hank Snow’s ‘I’m Moving On,’ and every time he toured, they’d want to hear that.”

In the ’80s, Frank Sinatra once opened for Willie at the Golden Nugget in Las Vegas, and they appeared together in a TV spot for NASA. Willie considered Sinatra a close friend. These two icons could not seem more different, and yet both were utterly unique vocalists who reinvented their genres.

“Do you feel like you learned anything from Sinatra?”

“I learned a lot about phrasing listening to Frank,” Willie said. “He didn’t worry about behind the beat or in front of the beat, or whatever — he could sing it either way, and that’s the feel you have to have.”

I asked about Frank’s work in the ’70s, when he turned out all those weak pop songs. I wondered if, after you get to the top, it’s easy to lose your way.

“You’ve got these guys over here saying you ought to do this and those guys over there saying you ought to do that,” Willie responded. “Next thing, you don’t know what to do.”

Willie was almost out of time. In a few minutes he’d have to head out onstage, where he’d summon all the ghosts, play all the hits. The audience would be older than it had been once, but you could tell the fans did not feel that age when Willie ran through “Whiskey River” and “If You’ve Got the Money I’ve Got the Time.” It’s the sort of music that makes you wish you were back at the beginning, when the road seemed like it would go on forever.

I stood and he stood, and we shook hands. I felt warmth pass from him to me. I told him what “Blue Eyes Crying in the Rain” had meant to me when I was 22. He nodded like he already knew. Then, before he could slip away, I asked him the secret of life.

“It’s simple,” Willie said. Do what you want to do. “If I don’t want to do it, forget it. But if I do want to do it, get out of my goddamn way.”

Rich Cohen is the author of 13 books, the most recent of which is The Chicago Cubs: Story of a Curse.

Editor’s Note: This story was updated to remove a song that was mistakenly listed as one Nelson composed.

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