Wyoming Mourns Country Superstar Toby Keith, A Cheyenne Frontier Days Favorite

Wyomingites are remembering country music superstar Toby Keith, who died Monday. Country music star and Moorcroft native Chancey Williams said he'll never forget the time he got to sing “Should’ve Been a Cowboy” with Keith at Cheyenne Frontier Days.

Renée Jean

February 06, 202410 min read

Country music stars Chancey Williams, left, and Toby Keith perform Keith's smash hit "Should've Been a Cowboy" at Cheyenne Frontier Days.
Country music stars Chancey Williams, left, and Toby Keith perform Keith's smash hit "Should've Been a Cowboy" at Cheyenne Frontier Days. (Courtesy Chancey Williams)

The song that made Toby Keith famous was also a song that turned Wyoming heads, and it made special memories for one Wyoming cowboy in particular.

Country music star and Wyoming native Chancey Williams will never forget the time he got to sing the iconic song “Should’ve Been a Cowboy” with Keith on the stage at Cheyenne Frontier Days.

Williams was among the many Wyoming fans paying tribute to Keith in reaction to the superstar’s death Monday, after a bout with stomach cancer.

Keith, 62, had a special relationship with the Cowboy State, visiting many times to play at Cheyenne Frontier Days and other locations, Williams said.

“He was a staple in Cheyenne Frontier Days,” Williams said. “He played there every few years. I don’t know how many times he played there, but it was a lot. And I assume it was one of his favorite places to play, just because he came back a lot.”

Williams, who opened for Keith six times after rising to country music fame himself, said he’s often been asked by friends and family in Wyoming about Keith.

“He was just like you and I are here, he’s just like a Wyoming guy,” Williams said. “He’d be a guy that you might see at the bar having a beer with his friends. He treated everybody so well, and I can’t say enough good things about him. He treated me so good, and it’s just a sad loss for everybody.”

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The Making Of ‘Should’ve Been A Cowboy’

Keith told the story a few times of how he bumped into one of his greatest hits, a song that’s taken more than 3 million spins around the radio DJ block.

He was with a large group of pheasant hunters at a dive restaurant in Kansas, with a name riffing off of the television show “Gunsmoke.”

One of the guys on the trip tried to get a dance with a young cowgirl, who flat out turned him down. But, not 15 minutes later, she took off for the dance floor with a cowboy.

It was at that point someone in the group said the fateful words that would launch Keith’s music career.

“John, I guess you should’ve been a cowboy.”

Keith immediately heard a song in the words, and he wrote it all out in about 20 minutes, Jesse James riding shotgun, Gene and Roy stealing young girls’ hearts, and all.

That hit was the first of many for Keith over a career that spanned three decades. Keith had 32 No. 1 singles over that time and sold more than 40 million albums.

Some of his more recent hits included “Beer For My Horses,” “Red Solo Cup,” and “Red, White and Blue” (The Angry American). The latter touched off a public feud between Keith and Natalie Maines of the Dixie Chicks.

“He didn’t sugarcoat things,” Williams said. “Toby was Toby. That’s what made him who he was and, some of the controversial things, you know, people either liked him or didn’t like him, and he didn’t really care. Toby was himself.”

Like A Wyoming Cowboy

Wyomingite Jim Wilkinson, recalls being a DJ at KMUS in Cheyenne when “Should’ve Been A Cowboy” first hit the airwaves.

“I’ll never forget it,” he told Cowboy State Daily. “I loved it the first time I ever played it on the radio.”

He felt sure the Oklahoma kid was going to be a hit in Wyoming from the moment he heard the song, but it was bucking all the supposed “right” trends for a No. 1 song.

“You mentioned cowboys in the ’90s, and that didn’t really constitute, you know, No. 1 songs,” Wilkinson recalled. “But the video was really cool.”

One notable thing fans might notice on the video is that Keith wasn’t wearing a cowboy hat at the time. That was probably down to what record companies then believed would make a song a hit.

“Record companies do that to you. They have a certain look they want you to have,” Wilkinson said. “And some artists go, ‘I don’t want to look like that. I want to look like me.’ But, you know, they do it for awhile until they get their foot in the door. And then, when you get a No. 1 song, you can pretty much do what you want to do.”

It didn’t take Keith long after “Should’ve Been a Cowboy” to evolve his look.

Within a couple of years, he was appearing on stage with a beat-up cowboy hat. It was part of his signature look on stage and off.

Country music stars Chancey Williams, left, and Toby Keith perform Keith's smash hit "Should've Been a Cowboy" at Cheyenne Frontier Days.
Country music stars Chancey Williams, left, and Toby Keith perform Keith's smash hit "Should've Been a Cowboy" at Cheyenne Frontier Days. (Courtesy Chancey Williams)

About Cheyenne Frontier Days

Keith was one of Cheyenne Frontier Days’ most prolific artists, CFD Contract Acts Chairman Scott Lewis told Cowboy State Daily, playing for almost 150,000 fans at CFD over the course of nine appearances.

One of the things he particularly liked about Cheyenne was its connection to the military base nearby, F.E. Warren.

“A lot of his shows were tributes to the military,” Lewis said. “And every show he was here, he would honor the military. He did that all over the world.”

One of the most memorable shows Keith did was in 2005, he said.

“That was when he came to Cheyenne Frontier Days for the Chris Le Doux tribute, and he played that two nights back to back,” Lewis said.

Williams was among those in the audience for that tribute, which was well before he’d had the chance to meet Keith and become one of his summer interns.

Williams still remembers thinking how cool it was that a superstar like that would make his whole show about someone else.

“I’m not sure if a lot of people remember that or knew that, but it was a cool thing Toby did for Cheyenne Frontier Days,” he said.

That wasn’t the only time, either, that Keith did something like that.

“When Merle Haggard got sick on his last show, Toby stepped in and sang Merle’s whole show,” Williams said. “And Merle asked him, you know, what songs of mine, and Toby said, like, all of them, because I literally know all of them.”

That was possible, Williams said, because Keith had a photographic memory. He didn’t have to practice songs over and over. He just needed to hear them once, and that was it.

Shining the spotlight on someone else at the right moment was just another example of the kind of man Keith was, Williams added.

“Instead of, you know, taking all the credit for his own show that day, he wanted to pay tribute to Chris and Cheyenne,” he said. “And that was really neat.”

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That Time When Toby …

One of Williams’ favorite memories with Keith started out as a 2 a.m. joy ride in Cheyenne.

“I was in my hotel room, and Toby had flown in late,” Williams recalled. “The front desk called up and said, ‘Hey, Toby Keith’s down here.’”

When Williams got on the line, Toby said, “Hey get down here.”

“So, I go down and it’s like 2 in the morning,” Williams said. “They had just flown in and Toby’s like, ‘Where’s your van at? Let’s go drive around.’”

Keith and Williams climbed in the back of the van, along with the rest of Keith’s entourage.

“Jason the security guard drove us around for an hour or so and then Toby’s like, ‘Let’s go get some more beer,’” Williams said. “And I was like, ‘Well, you know, they don’t sell beer after 2 in Wyoming.’”

Keith thought about that for a second, then his eyes lit up.

“He said, ‘I know where there’s some beer,’” Williams said. “So we drive out to the airport and keyed into the tarmac and just nosed my van up to his jet.”

They were having a few more beers on Keith’s jet, drinking the night away into the morning, when Williams mentioned how much he loved the song, “Should’ve been a Cowboy.”

“I was kind of joking you know, saying I’d been practicing ‘Should’ve Been a Cowboy’ my whole life and that I’d love to sing it with him sometime,” he said.

Keith looked Williams straight in the eye and said, “Be there tomorrow.”

Williams, however, didn’t quite believe the superstar was serious — not until he was actually up on the stage beside him, singing that song with the guy who has long been a hero to him.

“You know, there’s only a few superstars, and Toby was one of them,” Williams said. “And for an artist like that to let, you know, a kid from Wyoming sing his No. 1 song, his biggest song — not a lot of artists would do that.”

But it was just one of the many ways Keith had of making the people around him feel special, like they were the superstar.

Van Ride To Red Carpet Glory

The joy ride in Cheyenne wasn’t the first time Williams got to drive Keith around in his 1995 Chevy van.

Williams had driven the old van to Nashville when he was interning with Toby Keith’s manager as part of the conclusion of his master’s degree in public administration.

Williams had lucked into the internship because his family were friends with Le Doux, and the manager for Le Doux happened to also manage Keith.

“That was the van I used to rodeo out of,” Williams said. “And so, you know, we pulled up one night to drop some things off, and Toby was going to get in this limo to go to the BMI Awards, the red carpet.”

Seeing the van, Keith asked whose it was, Williams recalled. Learning it belonged to his new intern, Toby decided to take it instead of the limo.

“So Toby and all of his entourage jumped in my van, and we headed for the red carpet at the BMI awards,” Williams said. “And you know, it’s all limos and black cars, and then this old ’95 Chevy van.”

Keith told Williams to stay right where he was, even though all of the traffic directors kept motioning at him, trying to get that old van out of there.

“They didn’t know Toby was in there,” Williams said. “So, we get to the red carpet and Toby opens the door and says, ‘Hey, honk the horn.’ So I honk the horn, and out comes Toby Keith.”

That story is one of Williams’ favorites, in part because it just shows how down-to-earth Keith was. He could arrive for a Hollywood moment in some old van, like just plain folk, and yet command all the attention of a superstar, because that’s just who he was.

“He’s gonna be missed, you know,” Williams said. “In the world, in the music business, and for me personally. I know I’ve always looked up to him as an artist, and when we got to go on tour with him, I would just stand on the side of the stage and watch everything he did.

“You don’t get that opportunity a lot to watch a superstar like that do what he does.”

Chancey Williams, left, and Toby Keith
Chancey Williams, left, and Toby Keith (Courtesy Chancey Williams)

Renée Jean can be reached at renee@cowboystatedaily.com.

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Renée Jean

Business and Tourism Reporter