Toby Keith – “Should’ve Been a Cowboy” Lyrics Meaning

Photo of author
Written By Joanna Landrum

Joanna holds a BSc in English Literature and uses her expertise in literary analysis to uncover the deeper meaning of her favorite songs.

Toby Keith’s “Should’ve Been a Cowboy” is a twangy country anthem about unfulfilled dreams and the road not taken. Keith explores a romanticized vision of cowboy life through the song, painting it as an ideal place for freedom, adventure, and romance. Here, he’s not just talking about himself; he’s giving voice to anyone wishing for a simpler, more exhilarating life. The message is clear: Many of us yearn for an alternate reality but rarely get to experience it. The song is rooted in the era of Western movies and legends like Gene Autry and Roy Rogers. Keith wrote it as a tribute to those fantasies and a reflection of his longings.

Ready to saddle up for a journey into the Wild West of song lyrics? Keep reading to unpack this cowboy tale, note by note.

“Should’ve Been a Cowboy” Lyrics Meaning

Right from the first verse, Toby Keith introduces us to Marshal Dillon and Miss Kitty, characters from the iconic TV show “Gunsmoke.” Marshal Dillon, the fearless lawman, has a complex relationship with Miss Kitty, the saloon owner. But they never end up together. And this is where Keith says, “I should’ve been a cowboy.” He’s noting the missed opportunities and the untaken risks—basically, the what-ifs that we all contemplate.

Moving on to the chorus, Keith lays it bare. He wanted to “learn to rope and ride,” like the cowboys from the movies he admired—Gene Autry, Roy Rogers. These men stole hearts and rode into sunsets, embodying American masculinity and freedom. It’s not just about learning cowboy skills; it’s about the entire lifestyle, the allure of living life with few rules, taking risks, and having the courage to chase dreams.

The second verse delves into the imaginary adventures Keith would have embarked upon: chasing outlaws like Jesse James and living life on the edge as a Texas Ranger. It’s evident that the “west” represents not just a location but a state of mind where he can chase his dreams without holding back.

The line “California’s full of whiskey, women, and gold” echoes the Gold Rush and the fantasies of a promised land, where dreams can come true if you’re brave enough to chase them. Even in the desert nights, there’s a dream in his eye and a “prayer in my heart.”

And then we return to the chorus, this time with a bit more conviction. It’s not just a daydream anymore; it’s a missed calling, a palpable regret.

The Story Behind “Should’ve Been a Cowboy”

When Toby Keith wrote this song, he was a young man with a life ahead of him but filled with a certain kind of nostalgia for a life he never got to live. He had grown up watching Westerns, filled with larger-than-life heroes who lived by their own rules. Although he carved his own path in the music industry, the cowboy ethos had a lasting impact on his vision of freedom, masculinity, and American culture.

As he penned down the lyrics, he wasn’t just reminiscing or fantasizing; he was acknowledging the dreams left behind. At this point in his life, Keith was making choices about his own career, debating whether to fully plunge into the music world or follow another path.

The song serves as both a tribute and a confessional. It’s an ode to the cowboys and western heroes who influenced generations with their unwavering ideals of freedom and daring adventures. But it’s also a confession from Keith himself, admitting his yearnings and paying homage to the culture that shaped him.

In essence, “Should’ve Been a Cowboy” encapsulates the complexity of longing for a different life while still appreciating the one we have. It’s this universality that has made it one of the most enduring country songs of its time.