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Should’ve Been a Cowboy: A Look Back at Toby Keith’s Debut Smash
Toby Keith’s “Should’ve Been a Cowboy” isn’t just a catchy tune, it’s the song that launched his country music career. Released in 1993 as the lead single from his self-titled debut album, the track became an instant hit and went on to be one of the most-played country songs of the entire 1990s.

But where did this ode to the romanticized cowboy life come from? The inspiration struck Keith in a rather unexpected place: a hunting trip. On a pheasant hunt with friends in Dodge City, Kansas, Keith witnessed a fellow hunter get rejected on the dance floor while still in his hunting clothes. This seemingly ordinary moment sparked the now-iconic lyrics, “Should’ve been a cowboy, singin’ sweet songs, never workin’ all these long days gone.”

The song takes us on a journey through the narrator’s daydreams of a simpler life under the western sky. Keith namechecks legendary singing cowboys Gene Autry and Roy Rogers, referencing the romanticized Wild West portrayed in classic films. “Should’ve Been a Cowboy” isn’t just about the allure of wide-open spaces and horseback riding, it’s about the yearning for freedom and adventure – a sentiment that clearly resonated with country music fans.

The song’s success propelled Toby Keith into the spotlight, establishing him as a major voice in country music. “Should’ve Been a Cowboy” remains a fan favorite, a reminder of the simple yet powerful themes that continue to define Keith’s music. So crank up the volume and get ready to tap your boots as we revisit this classic anthem of the open range.

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