Toby Keith – Should’ve Been A Cowboy

Keith, a native Oklahoman with a gruff baritone and a penchant for storytelling, arrived on the scene with a sound that was both fresh and familiar. Country music in the early 90s was undergoing a bit of a shift. The polished “Urban Cowboy” sound of the 80s was starting to fade, and a new generation of artists, hungry for something more raw and rootsy, was emerging. Keith, with his unpretentious lyrics and a sound that drew heavily on classic honky-tonk and outlaw country influences, embodied this movement perfectly.

The mastermind behind the production of “Should’ve Been A Cowboy” was the legendary Billy Sherrill. Sherrill, known for his work with artists like George Jones, Tammy Wynette, and Tanya Tucker, was a country music heavyweight. His production style, characterized by a prominent steel guitar and a driving rhythm section, was a perfect fit for Keith’s gruff vocals and the song’s overall feel.

Now, let’s delve into the song itself. The opening line, a simple yet evocative “Yeah, I should’ve been a cowboy,” sets the stage for a daydream of a different life. The narrator, a man stuck in a monotonous, white-collar existence, longs for the freedom and adventure of the open range. The lyrics paint a vivid picture of cattle drives, dusty trails, and nights spent under a star-filled sky. There’s a touch of humor too, with the narrator imagining himself charming the barkeep’s daughter, a far cry from the office routine he’s currently enduring.

“Should’ve Been A Cowboy” is more than just a romanticized view of the cowboy life. It’s a song about missed opportunities, about the yearning for a simpler, more self-defined existence. It’s a sentiment many working folks can relate to, that feeling of being trapped in a situation that doesn’t quite fit. Keith captures this feeling perfectly, with his signature vocals adding a layer of authenticity and lived-in experience.

The song’s success wasn’t just about its relatable lyrics and catchy melody. The music video, featuring a young Keith roaming a dusty Western town, further solidified the song’s place in country music history. “Should’ve Been A Cowboy” became an anthem for a generation, a song that continues to resonate with listeners today. It’s a testament to Toby Keith’s talent as a songwriter and performer, and a reminder of the power of country music to capture the simple dreams and frustrations of everyday life.