How Toby Keith Scored an Unlikely Massive Hit With His First Single

When Toby Keith released his debut single, “Should’ve Been A Cowboy” in 1993, neither he nor country music was likely aware of the impact the song would have, both on his career and the entire genre as a whole. The song, from his freshman Toby Keith album, became his first No.1 hit. Written solely by Keith, “Should’ve Been A Cowboy” kick-started a career that remained strong until he passed away in 2024 from stomach cancer.

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“Should’ve Been A Cowboy” not only became his first chart-topping single, but also one of his most successful. The song was certified platinum four times. It also stayed in the No. 1 spot on the charts for two weeks.

A strong start to a legendary career, “Should’ve Been A Cowboy” is the only No. 1 song from Toby Keith. The other three singles, “He Ain’t Worth Missing”, “A Little Less Talk And A Lot More Action”, and “Wish I Didn’t Know Now” all became Top 5 singles for Keith. His next No. 1 single after “Should’ve Been A Cowboy” is “Who’s That Man”. The song, also written just by Keith, is the debut release from Keith’s sophomore Boomtown album.

How Toby Keith Wrote “Should’ve Been A Cowboy”

Keith was on a hunting trip when he had the idea to write “Should’ve Been A Cowboy”. He was out to dinner with the other men in the group, when one of the men in the group tried to dance with a younger woman, and was promptly rejected.

“She guns him down, and everyone makes fun of the poor guy,” Keith recalls to Pasadena Star-News. “He comes back to the table, and a young guy, about half his age, swoops in and takes her to the floor. One of them turned and said, ‘John, you should’ve been a cowboy.’ I thought, well, I have to write that.”

In a separate interview with The Oklahoman, Keith recalls the lengths he went to so he could write “Should’ve Been A Cowboy”.

“We were all two hunters to a room,” Keith recounts. “And my roommate was Freddie Cortez. He’s passed away now, but he used to own Chastain’s and a bunch of country bars in town. Freddie went to sleep, and I didn’t want to wake him, ‘cause he was hateful when you’d wake him up. I went in the bathroom, shut the door, wrote it down, put it in my bag, and went hunting the next day. Came home, revisited it, and said ‘I’m gonna record this song.’

“It’s the foundation for me of everything,” he adds.

For the remainder of his career, Keith played “Should’ve Been A Cowboy” during all of his live shows.

“It’s such an important piece of the puzzle. … When your first one is that big, it gives you a little breathing room to feel your way around,” he says. “Whereas there’s so many people that are really talented that lost their opportunity to have success because their first couple of songs weren’t hits.”

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