Discover the Cowboy Soul in “Should’ve Been A Cowboy” by Toby Keith

On the 12th of February in 1993, Toby Keith unveiled “Should’ve Been a Cowboy” as his initial foray into the music world, marking the beginning of his self-titled debut album. Shortly thereafter, the track ascended to the pinnacle of both the Billboard Hot Country Songs and the Canadian RPM Country Tracks charts, even achieving modest success on the mainstream Billboard Hot 100, where it landed at No. 93.

What truly set “Should’ve Been a Cowboy” apart was its overwhelming popularity on country radio, amassing over three million spins and clinching the accolade of the most broadcasted country tune of the 1990s.

The song has also etched its place in the traditions of Oklahoma State University, becoming an anthem played over the PA system after sporting events, echoing through the stadium or arena as crowds make their departure.

Delving into the Essence of the Song Crafted by Toby Keith himself, “Should’ve Been a Cowboy” weaves a nostalgic narrative inspired by the quintessential Western film genre. The protagonist of the song is enamored with the idealized cowboy lifestyle depicted in timeless Westerns, including the storied Gunsmoke series, where the venerable Marshal Dillon perpetually misses his chance with his beloved Miss Kitty.

The chorus of the song pays homage to the legendary cowboy figures Gene Autry and Roy Rogers, while also evoking imagery of six-shooters and the epic cattle drives synonymous with cowboy lore.

The song’s narrative is a vibrant tapestry of the protagonist’s imagined cowboy adventures, filled with whimsical companions reminiscent of Tonto or Gordito, a westward journey to the golden shores of California, and the daring pursuit of the infamous Jesse James alongside the Texas Rangers, encapsulating the essence of the Wild West’s allure.

Embark on a journey into the heart of the cowboy ethos with Toby Keith’s “Should’ve Been a Cowboy,” a spirited ode to the wanderlust and rugged charm of the cowboy way of life. Hit play below and let the adventure begin!