About the song

In 1993, Toby Keith exploded onto the country music scene with his debut single, “Should’ve Been a Cowboy”. This rowdy anthem instantly defined Keith’s brand of no-nonsense, working-class country, establishing him as a major force within the genre. “Should’ve Been a Cowboy” remains one of Keith’s most recognizable and beloved songs, forever associated with his swaggering persona and classic country sound.

A product of Keith’s own penmanship, “Should’ve Been a Cowboy” was crafted with the help of his long-time production partner, Chuck Cannon. Released as part of his self-titled debut album, the track showcased Keith’s unapologetic embrace of traditional country themes. Images of the American West, hard work, and an independent spirit permeate the song, appealing to listeners who longed for an authentic, no-frills country sound.

The song’s infectious energy and catchy melody propelled it to the top of the Billboard Hot Country Songs chart within a few short months. It spent an impressive two weeks at the coveted number-one spot, marking Keith’s very first chart-topping single. “Should’ve Been a Cowboy” cemented the Oklahoma native as a rising star and sparked a decades-spanning career filled with hits that celebrate classic American values.

The song has become an enduring cultural staple. Its frequent use in commercials, sports events, and movies has ensured its place in the country music canon. “Should’ve Been a Cowboy” isn’t simply a song—it’s shorthand for a certain kind of rugged, independent spirit that has continued to capture the hearts of country music fans for decades.