Keith, a native Oklahoman with a gruff baritone and an everyman persona, rose to prominence in the early 90s. Country music at the time was experiencing a shift, with slick production and pop sensibilities making inroads. “Should’ve Been a Cowboy” stood out as a breath of fresh air.
It was a declaration of nostalgia, a yearning for a simpler life, wrapped in a catchy melody and a relatable narrative.
Background
Keith paints a vivid picture of this romanticized past. He references iconic cowboy actors Gene Autry and Roy Rogers, figures who personified heroism and adventure on the silver screen.
He sings of learning to “rope and ride,” participating in a “cattle drive,” and serenading a sweetheart with “campfire songs.”
These lyrics tap into a deep-seated American mythos, one that glorifies the cowboy as a symbol of freedom, self-reliance, and connection to nature.
However, there’s a subtle undercurrent of regret in the song. The repeated line “I should’ve been a cowboy” speaks to a sense of missed opportunities, a yearning for a life path not taken.
This adds a layer of complexity to the song, making it more than just a simple ode to the Wild West. It’s a reflection on the choices we make and the paths we don’t take.
“Should’ve Been a Cowboy” was a critical and commercial success. It launched Keith’s career and became his signature song.
It reached number one on the Billboard Hot Country Songs chart and helped pave the way for the “neotraditional country” movement, a genre known for its focus on traditional country music instrumentation and storytelling.
Video
Lyrics
🎵 Let’s sing along with the lyrics! 🎤
I bet you’ve never heard ol’ Marshal Dillon sayMiss Kitty, have you ever thought of runnin’ away?Settlin’ down, would you marry meIf I asked you twice and begged you, pretty please?She’d have said, “Yes”, in a New York minuteThey never tied the knot, his heart wasn’t in itHe just stole a kiss as he rode awayHe never hung his hat up at Kitty’s placeI should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboy