Meaning of “Should’ve Been a Cowboy” by Toby Keith

Written By Michael Miller

Michael is a music teacher and professional cellist. He loves uncovering the deeper meaning of popular songs.

“Should’ve Been a Cowboy” by Toby Keith reflects the singer’s longing for the freedom and rugged individualism embodied by the cowboy lifestyle. The song crafts a vivid imagery of the Wild West and the iconic figures like Gene Autry and Roy Rogers, underscoring a desire to escape the constraints of modern life. The cowboy here symbolizes freedom, courage, and a connection to a simpler time. This playful and nostalgic journey is a way for Keith to explore themes of unfulfilled dreams and alternative paths in life.

You may feel like you’ve stumbled upon a forgotten path, one that takes you back to the dusty roads and untamed wilderness of the Wild West. It’s more than just the melody; it’s a trip to what could have been, and a glimpse into a world where life is a grand adventure. So, if you’re ready, let’s giddy up and dive deeper into this western tale full of wishes, dreams, and cowboy scenes.

“Should’ve Been a Cowboy” Lyrics Meaning

This song is packed with symbolic elements that convey a sense of yearning for a life unfulfilled. It opens with a reference to Marshal Dillon and Miss Kitty, characters from the TV series “Gunsmoke,” highlighting a romantic sentiment, suggesting a wish for a simpler, unhurried life.

In the chorus, Toby expresses his longing to have been a cowboy, emphasizing his desire to experience the cowboy lifestyle, which is synonymous with freedom, adventure, and bravery. “I should’ve learned to rope and ride,” illustrates a regret for not embracing the skills and attributes of a cowboy, emphasizing the escape it offers from contemporary constraints.

“Stealin’ the young girls’ hearts, Just like Gene and Roy,” here, Gene Autry and Roy Rogers, iconic singing cowboys of the silver screen, are symbolic of a lost era of heroism and romance. They signify a timeless appeal and a connection to the golden era of cowboys.

Furthermore, the mention of “runnin’ wild through the hills chasin’ Jesse James,” and “ridin’ shotgun for the Texas Rangers,” paints the picture of a life full of excitement and danger, embracing the lawlessness and valor of the Wild West.

The line “Go west young man, haven’t you been told? California’s full of whiskey, women, and gold,” reflects the notion of the West as a land of opportunity and pleasure, further deepening the sense of longing and unfulfilled dreams, portraying the West as a utopian escape.

Lastly, “sleepin’ out all night beneath the desert stars, with a dream in my eye and a prayer in my heart,” beautifully encapsulates the essence of this song – a dreamy desire for a life that symbolizes freedom, simplicity, and a connection to the land.

Why Was “Should’ve Been a Cowboy” Written?

To understand the background of this song is to delve into Toby Keith’s mindset and the inspirations behind his writing. During the time he penned this song, Keith might have been reflecting on the societal changes and the increasing complexity of modern life, leading to a nostalgic yearning for a bygone era. The cowboy, a quintessential figure representing autonomy and valor, emerged as a symbolic character in his narrative, embodying the ideals of a simpler, more authentic existence.

Keith’s creative process could have been influenced by a combination of his personal experiences, observations, and possibly, a desire to connect with his audience by exploring universally relatable themes of desire, freedom, and unfulfilled dreams. The song, in essence, is a poetic and musical exploration of an alternative reality, a what-if scenario that resonates with anyone who has ever pondered the road not taken.