Toby Keith Shares The Story That Inspired “Should’ve Been A Cowboy”

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Toby Keith recently shared the untold story of how his timeless hit song “Should’ve Been a Cowboy” came to life.

On January 3, 2024 – just one month before Keith passed away – behind-the-scenes details were unveiled in a video posted to Keiths social media, promoting what would end up being his last music release, 100% Songwriter, an album featuring a collection of some of his most cherished songs throughout his extensive career.

About “Should’ve Been a Cowboy”

“Should’ve Been a Cowboy” stands as a pivotal milestone in Keiths career, serving as his debut single and the lead track from his self-titled inaugural album in 1993. The track quickly gained popularity, becoming one of the most played country songs in the 90’s and solidifying Keith’s status as a prominent figure in the Country music genre.

The Story Behind “Should’ve Been a Cowboy”

In the video, Keith transported viewers back to the creation of “Should’ve Been a Cowboy,” recounting a hunting trip with a few friends in Dodge City, Kansas while still in the process of finishing up his first album. The atmosphere of the Ole West town they were in, reminiscent of the famous Gunsmoke series, lingered in Keith’s mind throughout the trip.

The moment that influenced the song unfolded during a memorable evening in a steakhouse bar. Decked out in hunting gear, Keith and his friends found themselves watching as a fellow hunter, named John, mustered up the courage to ask a cowgirl to dance. She ultimately rejected him, humorously prompting one of Keith’s friends to exclaim “John, you should’ve been a cowboy.”

The simplicity of that single line sparked immediate inspiration for a song in Keith’s mind.

“So I thought, ‘I’m going to write that.’ I took my guitar, sat on the side of the motel tub, and shut the door so no one could hear me,” Keith said in the video.

And just like that, in a mere 20 minutes, Toby Keith wrote one of his most significant hit songs.

Watch Toby Keith explain the backstory of “Should’ve Been A Cowboy” below:

Hear “Should’ve Been A Cowboy” and over a dozen of Toby’s hits he wrote solo on his 100% Songwriter album! https://t.co/Psj9tvPwWx pic.twitter.com/POEZrD9y2a

— Toby Keith (@tobykeith) January 3, 2024

Toby Keith passed away on February 5, 2024 from a nearly three-year battle with stomach cancer, making his explanation of “Should’ve Been A Cowboy” that much more meaningful.