Stay sharp, get used to loss – and pay your taxes: the wit and wisdom of Willie Nelson

On being the Last Man Standing

Longevity is a blessing and also a burden. A blessing because you get to hang around to see your grandkids and maybe even your great-grandkids. But a burden because every day it seems like another friend has passed. Grieving becomes a full-time job. The last man standing can be lonely. Loss is something you don’t get over. That idea hit me hard when a friend’s wife died and he came to me for comfort. He saw me as a guy who might understand. The thing I know most, I told him, especially after my son Billy died in 1991, aged 33, is that you don’t get over it, but you will get through it. Best I can do is write a song.

On love and loss

I have to admit that I like songs about suffering love. I’ve experienced a lot of love, and certainly some suffering due to the loss of it. At age 10, when I put together a booklet of songs I had written, they had titles like Faded Love and Wasted Dreams and I Guess I Was Born to Be Blue. I’d already known a little something about pain and loss by then. My sister Bobbie and I felt the loss and abandonment of our parents, who left us with our grandparents when we were six months old, the kindness and love of our grandparents, and the loss of my grandfather, who taught me my first chords and bought me my first guitar. He passed, leaving my grandmother to raise us alone. All that love and loss by the age of 10. Some folks can live with heavy thoughts for a long time. Not me. I turn heavy thoughts into song. And the turning hardly ever fails to lighten the thought. It maybe even makes the thought disappear into thin air.

On meeting his fourth wife, Annie

The 1986 film Stagecoach was a remake of the classic western. I was shooting with Waylon Jennings, Kris Kristofferson and Johnny Cash. The Highwaymen had just recorded a huge hit album that gave new life to our middle-age careers. The script for the movie was, in the measured opinion of Kris (the only actual movie star among us), “a piece of shit”.

We didn’t argue with Kris. After all, he’s a Rhodes Scholar. Kris overlooked the lousy script, though, and went along because it was really just a way for us to all hang out together. We were brothers. I also went along because I love westerns, even bad ones.

In addition, there was this no-nonsense woman named Ann Marie D’Angelo who made things a lot easier. On my shoot days, I was in her makeup chair for a couple hours each day, and we were having a great time. She was smart and funny and spunky and cute. One day, the producer asked that my hair be cut for a scene. We talked about it for a while in the makeup trailer, and all the while it was like we’d known each other for ever, or maybe in another lifetime. Neither of us thought it was a good idea. “Let’s just tell them no,” I said. That was the end of it. It didn’t feel like the first decision we’d made together, and as it turned out, it wouldn’t be the last. It was all so natural, like singing a verse into the chorus of a song.

On marriage

Annie and I have clocked more than 35 years together. That’s a record for me. I was with my first wife, Martha, for 10 years; my second wife, Shirley, eight years; and my third wife, Connie, for 17 years. These were all good women who married a man who, despite being unsuitable for marriage, kept getting married. Why? I love family and kept dreaming of having one big happy family. Maybe it’s also because my own mom and dad never stayed together long enough to raise me and my sister.

Annie once told me, “I was sceptical of us. I had three dating rules: don’t date a divorced man, don’t date a man with kids and don’t date a celebrity. I was striking out in all three categories. But I felt this immediate connection.”

I shared some of Annie’s feelings about getting involved. I’d messed up three marriages because I didn’t take the time to look at my own behaviour, to fix what was wrong. I had a valid excuse to always be on the road: I made my money on the road, and the road was something I could never quit. The road was where I got to see my fans. I could never abandon my fans, because my fans have never abandoned me.

On raising kids on the road

After Annie and I had our sons Lukas and Micah in 1988 and 1990, the bus was our home and for several years became their classroom. The people they met and the places they travelled were the base of their education. Geography was easy because they could learn about wherever we were. On the road, the world was their textbook.

Someone asked Annie once how we were able to raise such centered, stable kids on the road. “Teaching kids to be responsible and accountable is easy, as long as you are responsible and accountable parents. When they see it, they learn it. If they are not behaving well, you let them know you know it,” she said.

On fighting the IRS

I told Annie it would always be smooth sailing … but man, was I wrong! I didn’t see the storm coming. The same year of Micah’s birth, the IRS showed up, guns blazing. Froze my bank accounts. Grabbed my assets. Seized my property. Padlocked my homes. Said I owed them $32m. That was the start of the 1990s, when suddenly God’s problem child had a problem. We were in the middle of a tour when we got a call telling us the IRS had seized our property and were auctioning off our personal belongings.

We asked my tax attorney Larry Goldfein to let them know our answer was fuck, no.

But out of that came more negotiations. The auctions stopped, but before they did, many of our good friends went in and bought a lot of our properties, and some of our personal belongings. They let us buy them back when everything was settled. We were grateful to have such great friends.

While the ranch was seized, we moved into a condo next to the studio. All four of us squeezed into a one-bedroom until things were settled. It was actually a special time, if also uncertain.

Eventually, I made a deal to give them an album called The IRS Tapes: Who’ll Buy My Memories?. We won our lawsuit, and the album paid off our debt; we moved back to the ranch and life resumed as usual. After that, I always made sure my taxes were paid. Or at least Larry Goldfein did. He is still with me today.

On family rules

“Don’t be an asshole, don’t be an asshole, don’t be a goddamn asshole.”

We really do live by it. If we had to define it, it would be saying, “Don’t expect anything you haven’t worked for. Forget nepotism. Treat others the way you want to be treated. And if you want to be treated like an asshole, be one.”

On touring with country music pioneer Ray Price in the 1960s

I was going wild. That’s because, for the first time in my life, I had money. My hit songs were hitting even harder. Every night was a party, and the party was on me. I booked big suites at the hotels and treated the boys in the band to all the booze they wanted. I drank like a fish and acted like an ass. It didn’t take more than three weeks for me to run through all my money. Like a patient father, Ray watched me play the fool and didn’t say a word until I was dead broke.

He didn’t chastise me; he advised me. He saw that I was speeding down a dead‑end street. Didn’t it make sense to slow down and turn around?

I couldn’t argue with Ray. He was seven years my senior. He had built a career driven by positive direction. Even in my boozy condition, I recognised positive energy. Ray’s energy was generous.

He was going to Nashville after the tour to record and invited me to play on his new album. He knew I was broke. The gig meant decent union pay. Ray also knew I didn’t know his new music and there wasn’t time to learn it. That’s why he handed me a guitar without an amp so I wouldn’t be heard. I pretended to play, and when the session was over, Ray pretended that I played well.

“Take this money, Willie,” he said. “Write me some songs, and leave the bottle alone.”

Took a long time – way too long – to renounce whiskey in favour of weed. But I never forgot how Ray looked after me.

On his friendship with Ray Charles

In the summer of 1984, at the Austin Opry House, I sat on a piano bench next to Ray Charles. We performed a live version of Seven Spanish Angels, a song we had just recorded at the studio on my ranch.

Ray rocked his body back and forth, singing, playing, bringing the song to life, bringing me to life, reminding me – showing me – that the payoff for living a life in music is the ability to express joy. Ray radiated joy. When he laughed, he laughed hard. He let himself go. He might fall to the floor in a fit of delight. When he talked, he might shout. His laughing and talking were a series of explosions. Just like his singing. He never ran out of breath. He never ran out of spirit. I’d never been with anyone so joyful.

On his song On the Road Again

I wrote it in 1980 in five minutes on an airplane for producer Sydney Pollack, who needed something in a hurry for a movie I was in. It won a Grammy and went to No 1. I play it at every show, not because the crowd demands it but because I love it. It defines me.

On keeping fit

It’s important for longevity. I’ve played softball and been a runner for years. I’ve also taken tae kwon do for years. It’s a mental and physical discipline that’s been good for my mental health, my strength, my breath and my music.

After I’d gotten my fifth-degree black belt, a reporter asked me when and why I’d started taking tae kwon do. I told him a funny truth. I started doing karate and judo off the backs of magazines when I was young, and I really liked it. After Annie put the boys in tae kwon do class when they were little, and then after she started taking it too, and then after they all started going once a week, I decided I’d better take it, too, for I kept – and keep – my mental sharpness by playing poker and dominoes. I also kept golfing, mostly on my nine-hole course at the ranch.

On poker and weed

The stakes in Django’s Orchid Lounge are not small. I like the thrill of winning and the danger of losing. Many players are regulars, Maui neighbours and pals like Woody Harrelson and Owen Wilson. Don Nelson, the former NBA coach, often shows up. Occasionally an inexperienced player will drop by, like singer Jack Johnson, who wrote a song about it called Willie Got Me Stoned and Stole All My Money. I plead guilty but will only add that his participation was voluntary.

For decades, those games had been played under a thick smog of weed. When I moved into my mid‑80s, that changed a bit. For a while I used a fancy Silver Surfer water bong that cooled the smoke and filtered the contaminants. Every time someone got on the bus and loved it, I gave it away. Silver Surfer sent me several of those bongs. Eventually, the bong ritual became too much and I started using a vape, which turned out not to be great for my lungs either.

I continued vaping, but when I was at Django’s, I would occasionally hit a joint. After all, I was the guy who wrote Roll Me Up and Smoke Me When I Die. But I always paid for it. I’d heard that “a hard head makes a sore ass” and I was proving it.

On ageing and performing

All my life I’d played standing up. At age 89, I had to make a big concession. Standing up for a 90-minute set just wasn’t easy. To get through a set, I had to sit down. I was initially resistant. My machismo put up an argument, but I talked myself into it. “Dude, you’ve earned the right. Sitting down will relax you. With Micah sitting on one side of you and Luke sitting on the other, it will be like jammin’ in the living room. The audience will feel the intimacy. It’ll be a good change.” It was. I was glad I relented. After doing it once, I could see doing it permanently. Sitting down had a way of bringing the audience closer to me. It was like I was sitting in their living rooms. It felt natural. Like I was taking it easy.

On the importance of listening

“If we were supposed to talk more than we listen, we would have two tongues and one ear” – Mark Twain.

That’s a quote I love. It’s also something I’ve tried to live by. Whether in an intimate setting with just a few family members and friends, or a bigger forum, my best move is to mainly stay quiet. That doesn’t mean I don’t have something to say. It also doesn’t mean that I agree with what’s being said. It just means that I’d do better by listening and not talking. And if I’ve enjoyed many beautiful lifelong relationships with family, friends and fans, it’s because I’ve followed that creed. Stay quiet. Just listen.

On the lessons he’s learned in later life

Do not go gentle into that good night,
Old age should burn and rave at close of day;
Rage, rage against the dying of the light.

I’m told that’s one of the most famous lines of poetry. It was written by the Welsh poet Dylan Thomas in 1947, when his father was dying.

I appreciate how a son doesn’t want his dad to die. I appreciate an attitude that says, “Don’t give up. Fight death with all you got.” Maybe that’s what I’ve been feeling. Do what you can do to stay alive. Keep writing, recording and touring. Keep singing. Keep raging against the dying of the light.

But maybe I haven’t been raging at all. Maybe I’ve just been doing what I’ve always done. Seems like my life has been lived out in two parts. The first part is living. The second part is writing and singing about living.

Shouldn’t we just embrace the good night? And shouldn’t our embrace be gentle? In my gentle embrace, I feel the need to ask my lungs for forgiveness. I loved smoking in my youth so much that I didn’t think twice about the damage I was doing to the body part keeping me alive.

Bless the breath. Bless gentleness. Learning to be gentler. Learning to be more patient. Learning to be patient with our own impatience. Learning to love all those who are close to us. Loving our family. Loving our friends. Learning to love people who don’t love us. Learning to be gentle with people who are raging with anger, and also learning to create boundaries to protect our own peace. Learning to be still while still moving. Learning that energy follows thought, and that generating positive thoughts isn’t all that tough. Learning to say thanks and be grateful. Thanks for letting me go on this ride. Thanks for letting me take this trip. I don’t know when the trip is going to end. But that doesn’t matter, because I do believe that when it does end, another trip will begin. And that trip, and the one that follows, will go into that good night for ever and a day.