That time Toby Keith sang ‘Should’ve Been a Cowboy’ at Eskimo Joe’s after Bedlam

That time Toby Keith sang ‘Should’ve Been a Cowboy’ at Eskimo Joe’s after Bedlam

Barry Switzer explains why he and Toby Keith went to Eskimo Joe's after Bedlam last season and wound up entertaining OSU fans after a Cowboy win.

Ben Hutchens

By Ben Hutchens

| Feb 6, 2024, 8:46pm CST

Ben Hutchens

By Ben Hutchens

Feb 6, 2024, 8:46pm CST

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STILLWATER — Tyler Adams is happy he didn’t get his phone out to record. 

The memory of country music superstar Toby Keith just feet away wearing a Sooner red shirt and gray beanie is still burned in his mind. A year later, he can still hear Keith singing  “Should’ve Been A Cowboy” to a group of Oklahoma State fans crammed around him in Eskimo Joe’s.

“I remember saying to myself, ‘Just live in the moment on this one, you don’t get to see this every day,’” Adams, a 2022 OSU graduate, said. “I was sitting right there next to Barry Switzer and Toby Keith as he performs, “Should’ve Been A Cowboy.” It was a pretty crazy moment.” 

Lucky for everyone else, there were plenty of cameras out and the clip of Keith singing went viral. 

Keith, 62, died Monday after a battle with stomach cancer. He had 20 No. 1 singles, the first of which became the most-played country song of the 1990s and a staple of Oklahoma State wins in Stillwater.

Keith and Switzer, the Sooners football coaching legend, were in Gallagher-Iba Arena to hear it on Jan. 18, 2023. They sat behind the Sooner bench and watched a 72-56 Oklahoma State men’s basketball win. 

Adams, who had just graduated from Oklahoma State, was back in town that night to watch the game with a friend. The deal was if the Cowboys won, they’d go to Eskimo Joe’s for a beer. If OSU lost, they’d go straight back to Oklahoma City. 

When Adams entered Joe’s through the east door and recognized Keith and Switzer sitting at the bar.

What were they doing there?

“Well, I think it’s kind of what everybody else does,” Switzer told on Tuesday. “Isn’t it the number one place to go? That’s why we went.”

Before long, Keith “was holding court with the entire bar, taking pictures, answering questions,” Adams said. Some accounts of the night have Switzer and Keith buying Fireball shots for the crowd. 

“Hell, I can’t remember,” Switzer said. “Maybe I had one too many shots.”

Adams approached and introduced himself to Switzer. That was when Keith got up from his stool.

“Alright, alright I’ll sing,” he said, clapping three times

“Should’ve been a Cowboy.” 

Clap, clap.

“Should’ve learned to rope and ride. Wearin’ my six-shooter, ridin’ my pony on a cattle drive.”

Keith turned to his left and pointed out someone in the crowd. 

“You ain’t singing.”

“… Just like Gene and Roy,” Keith picked up. “Singin’ those campfire songs, woah I should’ve been a cowboy.”

Hinckley estimates that 150 people ended up in the small room after the singing was over. Keith and Switzer talked with everyone and indulged selfie requests. Keith even gave the Oklahoma State fans a hard time, asking if they were going to let him sing wearing a Sooner hat and shirt. 

“We had a great time,” Switzer said. “First song he sings is ‘Should’ve Been a Cowboy.’ He sang the rest of the night. I sat at the bar and drank. Toby loved it.”

Adams said Switzer told him, “Stillwater has gotten kind of soft because 20 years ago we would have been tumbled out of town.” 

The party didn’t end when Eskimo Joe’s closed. Switzer and Keith walked across the street to George’s Stables, a bar that has karaoke every Wednesday. Keith was just warming up.

Toby opened with another rendition of his breakthrough song and Cowboy anthem.

“That set him on his way of singing the rest of the night,” Switzer said. “Everybody had a blast. It was a good night.”

Hinckley remembers the spirit Keith and Switzer inspired.

“Just how big of a heart they had and how they care about people and how memorable of a night that was. Just to see some of the most famous OU legends in one of the most famous OSU establishments and how they just morphed right into it.”


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Ben Hutchens and his twin brother Sam cover Oklahoma State for the Sellout Crowd. After a decade of living in the state, Ben finally feels justified in calling himself an Oklahoman. You can reach him at [email protected] and continue the dialogue @Ben_ Hutchens_ on social media.

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