About the song
“Should’ve Been A Cowboy” by Toby Keith. A veritable anthem for those who dream of wide-open spaces and a simpler life. Released in 1993, it wasn’t just the debut single for Toby Keith, a name soon synonymous with American bravado, but the launching pad for his entire career. The song itself was written by Keith, showcasing a talent for storytelling that would become a hallmark of his music.
This wasn’t your typical, syrupy country ballad. “Should’ve Been A Cowboy” bursts onto the scene with a driving rhythm section and Keith’s unmistakable baritone. The lyrics paint a vivid picture of a man stuck in a monotonous office job, yearning for the freedom and adventure of the cowboy life. We hear about starched shirts and fluorescent lights, a stark contrast to the dusty trails and starry nights the narrator craves. References to campfire songs sung by a fictional “Gina Roy” add a touch of whimsy, while the line “Concrete jungle where dreams turn to dust” perfectly encapsulates the yearning for escape.
This wasn’t just a hit, it was a phenomenon. “Should’ve Been A Cowboy” rocketed up the Billboard charts, reaching the coveted number one spot on the Hot Country Songs chart and staying there for two glorious weeks. It became Toby Keith’s signature song, a calling card that introduced him to a new generation of country music fans. The song’s success transcended genre, resonating with anyone who’s ever felt trapped by the daily grind and dreamt of a life less ordinary. Even today, “Should’ve Been A Cowboy” remains a country radio staple, a reminder of the enduring power of Toby Keith’s songwriting and a testament to the enduring allure of the cowboy myth.