40 Years on the Road with Willie Nelson: Inside Bus Driver Tony Sizemore’s Life with the Icon (Exclusive)

The music legend’s bus driver Tony Sizemore has done it all during his 40 years of touring him, from meeting U.S. presidents to being locked up

In 2019, Willie Nelson threw a retirement party for his longtime bus driver, Tony Sizemore. But before Sizemore could settle into a life of leisure, Nelson asked if he could stay on for just one more big show he had coming up in Tennessee.

One show quickly turned into dozens more, and four years later, Sizemore, 75, is still driving around the country legend — who turned 90 in April — on tour.

“Willie is just the kind of person that you can’t get away from him,” Sizemore tells PEOPLE with a laugh. “You talk about quitting, and he’ll say, ‘Wait a minute, wait a minute. Whoa, whoa. I’m 90. What are you talking about quitting for?’ He won’t let me quit, so I guess I just keep working.”

A Marine Corps veteran, Sizemore first started driving for Nelson in 1983, after working for the likes of Bruce Springsteen, Queen, Foreigner, Tom Petty, Peter Frampton, Marvin Gaye, Rick James, Jackson Browne, Kenny Rogers, The Oak Ridge Boys and Jimmy Buffett. At the time, Nelson was looking for a temporary driver who knew how to work a manual shift bus.

“They brought me out to drive that bus for what I thought would be a couple of weeks, and after a couple weeks I said, ‘Well, did you find anybody you like?’ Willie said, ‘Oh yeah, we like what we got. We’re good right now,'” Sizemore recalls. “So that was it. I’m still here.”

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In his 40 years on the road with Nelson, Sizemore, a St. Cloud, Florida, resident, has had countless once in a lifetime experiences, like meeting everyone from Dolly Parton to U.S. presidents.

“I graduated from a high school in small town Indiana that had 100 kids,” he says. “My class had seven boys and 20 girls. So, meeting the president was not on my priority list when I was in high school. When I was a kid, Mamie Eisenhower came through our town on the train, and my mother took us young kids out and waved at her. I figured that was about as close as I’d ever get to anybody.”

He’s also experienced everything from being locked up with Nelson for drug possession to witnessing the star autograph babies’ heads. “You can’t believe the stories,” he says.

Through it all though, it’s the moments with Nelson that Sizemore cherishes most.

“He’ll make a cup of coffee, and he’ll say, ‘Here, I’ll split this with you,'” he says. “He’ll pour half of his coffee in my cup. Sometimes I’m almost at the hotel when he does it, but I just act like I’m going to drink it anyway.”

“I turn 76 in September, and I still get happy talking about Willie,” he continues. “If I quit today and somebody else called me up, I probably would not go out. Willie’s the only person I want to work for, and he has been for years. It’s just because he’s such a nice man.”

Here are Nelson’s road rules, as told by Sizemore.

Treat Everyone Equal

We’ve had presidents, ex-presidents, want-to-be presidents, wrestlers, football players and movie stars on the bus, and Willie treats everybody the same.

We were playing some night shows in New York, and we parked in New Jersey. I went to the bus one day and Willie was sitting on the bus with this guy, I think he called him Louie. He said, “Hey, Tony, this is Louie. He lives in a box around the street there.” They were having coffee. We got ready to go and he said, “Well, I’ll see you later, Louie.” We went to the city and did our show, and then at midnight, probably, we started back out of the city and Willie said, “Tony, if you can find a donut shop, pick me up a couple dozen donuts.” Well, I’ve never heard Willie say that.

I said, “You’ve got a donut thing going on?” He said, “No. Louie’s coming back tomorrow to have coffee, and he said he’s going to bring a couple of his friends.” The next day, Louie did come back with a couple of his friends. So, everybody’s the same to Willie. And I found the donuts. If Willie says, “I want a donut,” I get a donut.

Open Door Policy

Dolly Parton is my all time favorite guest who has been on Willie’s bus. But I’ve had so many of them.

Years ago, we used to play Universal Studios in California for two weeks at a time. Every night Angie Dickinson would come to the show, and every night before she left the show, she’d come around and hug everybody’s neck and take care of everybody for being so kind to her. She always stuck out to me.

I took Melissa Etheridge in one time and introduced Willie to her. I met her at a truck stop one night, and she said, “Could I meet Willie?” I said, “Sure.” I said, “Just a minute,” and I went in and told Willie at 2 a.m., “Melissa Etheridge, she plays a really mean 12-string guitar and is a bluesy singer.” And he said, “Oh, bring her in.” I brought her in, and they talked for a few minutes, and he said, “Do you have any of your music I could get from you I could listen to?” She came out of the bus and she told her guys, “Tear that bus apart to find him a CD.” She hugged my neck and said, “Wow, Willie Nelson wants my music.”

Always Ask Annie

Willie’s wife [Annie D’Angelo], if I need something, it’s on my chair the next day. If I mention, “Oh, I lost my flashlight the other night,” the next day there will be one on my seat. She’s my best helper when I break down. If I have a problem, I want Annie helping me. She knows tools. She’s better than any driver I’ve ever had, because she doesn’t mind getting dirty and she’ll help you if she can.

Everybody’s Family

It’s Willie Nelson and Family, and he really means Willie Nelson and Family. My son is 39, and he grew up with Willie. Every summer he’d ride the bus with me and meet all the entertainers. They’d always give him a little job on stage like setting up the water when he was little. As he got bigger, he’d move carts and things.

If Willie Can’t Get You Out of Jail, He’ll Get in With You

I’ve been busted with Willie a couple of times. I don’t smoke, but they put us in jail in Sierra Blanca, which is about 80 miles outside of El Paso. Coming across I-10, they smelled pot in the bus and they arrested us and they put us in the holding cell, and Willie started singing, “Nobody knows the trouble I’m in.”

We’ve been arrested a few times for pot over the years. In Louisiana, they got us. This police officer, the last thing he told us was, “Don’t worry Mr. Nelson, we’ll keep this off the news.” He gave everybody a ticket in the bus and put our ages on it. My son was in the Marine Corps in Al-Fallujah, Iraq, at the time, and his friends were on the internet, and at the bottom of the screen it scrolled across, “Willie Nelson’s been busted,” and it told all our ages and names. One of the guys said, “Is this your dad?” He said, “Well, yes it is.” So he called me from the company office and asked me if I was OK. I said, “Yes, I’m OK, son. I’m not even in Austin yet and it’s already got to Iraq.”

Willie told me one time, he said, “If I can’t get you out of jail, I’ll get in with you.” If you go with Willie, you get out fast.

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Take Care of Trigger

Willie’s guitar, Trigger, can be sitting in the middle of the floor, and people — great entertainers, great guitarists — will walk around that guitar and look at it. They won’t pick it up unless Willie tells them to. It’s kind of funny to see that.

We played for Robert Redford at the Kennedy Center Awards [in 2005]. Every time I’d go through Secret Service, I’d take Trigger out of the case, show it to them, and then set it up for Willie. When we got ready to walk back out, I’d take Trigger with me, and this Secret Service guy said, “Why don’t you just leave that guitar in here?” I said, “Well, you don’t leave the President by himself, do you?” We guard Trigger with our lives. I’ve got a safe at my house that I bought just for Trigger. If Trigger’s in my bus, I take Trigger out and put it in that safe.

don’t want to be known as the guy that lost Trigger.

Willie says when Trigger quits, he quits.

Laughter Makes Life Go Round

My bunk used to be above Willie’s sister Bobbie’s (she died in 2022), and there used to be a space in the corner of the bunk where we had an air conditioner running up and down it. After we remodeled the bus, we took that out, and that little corner was open. I got in the bunk and pulled my glasses off, put them in the corner, and went to sleep. At about 4 a.m., it was my turn to drive, but when I got up, I couldn’t find my glasses. I said, “Oh no.”

I thought, “Shoot, my glasses must be in Bobbie’s bunk.” Bobbie was asleep. I asked Willie’s daughter Lana, “Lana, could you check over there and see if my glasses are in Bobbie’s bunk?” She said, “Well, I won’t ask any questions, but I’ll look.” Bobbie woke up and she said, “Tony lost his glasses in your bunk, Bobbie.” She said, “Well, he could have got in here and looked for them.”

Later on that day we were parked and Lana said, “Well, Dad, I guess I might as well just tell you. Tony lost his glasses in Aunt Bobbie’s bunk last night.” He said, “I thought there was something going on.” Bobbie said, “Don’t you guys worry about it.”

They all have a great sense of humor. Willie has the best. He’s got a million jokes, which he’ll tell me in the middle of the night.

Fans Come First

Everybody thinks marijuana is Willie’s drug of choice, but the audience is. I said one time that you can get drunk and miss a show, that’s OK. But if he catches you being rude to one of his fans, then that’s a no-no.

Willie used to sign autographs for three or four hours every night after the show. He’d sign every autograph there and take pictures. He has this uncanny ability for that one moment he’s talking to that person where he looks them right dead in the eyes. Older people and younger people both will walk off saying, “Wow, he talked to me.”

One time we were in Indianapolis, and we were parked on grass. These buses don’t like grass when it rains, and I could see the rain coming. Whenever he’d sign autographs, I’d always get the older people and the handicapped people up and say, “I’m with Willie, let me walk you up to the front of the line.” He had a big line of people, so I got this lady who was pushing another lady in a wheelchair and brought them to the front. The lady said, “Thanks. This is my mother, and she’s 100 years old.” I’m still thinking it’s going to rain, so I said, “Well, let’s hurry. We don’t have much time.” The old lady shook her fist at me! I said, “No, no! I mean it’s going to rain.”

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When we got there, Willie squatted down with them and took pictures. As they left, the old lady waved at me and told me goodbye. I have so many fun memories over the years, and I’ve even seen Willie sign babies’ heads.

Once, some kid took a real thick piece of leather and tooled it. He put wrinkles in it and then he painted it. It was the most beautiful picture I’ve seen of Willie yet. The tooling, the wrinkles, and everything about it was just beautiful. Well, he gave it to me and said, “I know I can’t give this to him, but would you give this to Willie?” I said, “Yes, I will. When I get time, I will.”

About 3 a.m. I stopped, and I got fuel, and I said, “Oh, Willie, here’s a picture this kid asked me to give you.” I took it back to Willie and Willie said, “Well, this is really nice. Let me use your phone.” He called this kid, because the kid’s number was on the back of it. This kid said, “Willie Nelson! Willie Nelson!” I said, “Willie, you’ve just gotten this kid in a lot of trouble.” He said, “What do you mean?” I said, “Well, tomorrow he’s going to go to work and tell everybody you called him at 3 a.m., and you know what they’re going to say. They’re going to call him a liar.” He said, “Oh yeah. Well, here, take a picture of me holding this up and send it to the kid.” So I did. The kid wrote me the nicest thank you and said, “Thank you so much for doing that. I’ll treasure this picture and that phone call for the rest of my life.”