About the song
Toby Keith’s Should’ve Been a Cowboy isn’t just a song—it’s an anthem, a defining piece of ‘90s country that captures the spirit of the American West with an effortless blend of nostalgia, longing, and rugged independence. Released in 1993 as the debut single from Keith’s self-titled album, the song immediately struck a chord with audiences, catapulting the then-unknown Oklahoma singer into the national spotlight. More than three decades later, it remains one of the most enduring country songs of its era, a staple on jukeboxes, country radio, and honky-tonk dance floors across America.
At its core, Should’ve Been a Cowboy is a celebration of the cowboy mythos—the romanticized, larger-than-life image of gunslingers, outlaws, and frontier heroes that has been immortalized in film, literature, and, of course, country music. Keith, with his signature baritone and easygoing delivery, sings from the perspective of a man who laments missing his chance to live the cowboy life, wistfully imagining himself riding through the West, chasing desperados, and winning the hearts of fair maidens. It’s a playful but deeply evocative premise, one that taps into a universal sense of nostalgia—who hasn’t, at some point, fantasized about stepping into the boots of a legendary figure from another time?
Musically, the song is pure ‘90s country gold. The arrangement is polished but retains enough twang and warmth to feel organic. A bright electric guitar riff opens the track, immediately setting the tone with an infectious melody that’s both inviting and familiar. Steel guitar weaves through the mix, adding that unmistakable country shimmer, while the rhythm section keeps things driving but relaxed, perfectly complementing Keith’s vocal performance. There’s an undeniable sense of freedom in the song’s movement—it’s the kind of track that makes you want to roll down the windows and take a long drive on an open highway.
One of the reasons Should’ve Been a Cowboy remains so beloved is its lyrical craftsmanship. Keith doesn’t just list cowboy tropes—he paints vivid scenes, referencing figures like Gene Autry and Roy Rogers, evoking imagery of campfires, wide-open plains, and saloons filled with high-stakes adventure. The song’s charm lies in its ability to balance humor and sincerity; it never takes itself too seriously, yet there’s a genuine reverence for the cowboy ideal that gives it depth.
The impact of Should’ve Been a Cowboy was immediate and far-reaching. It became the most-played country song of the 1990s, a remarkable feat for a debut single. It established Toby Keith as a formidable presence in the genre, paving the way for a career that would span decades and include numerous chart-topping hits. More importantly, the song became a cultural touchstone, embraced by country fans of all ages as a joyful, escapist anthem.
Even today, the song’s appeal hasn’t waned. It continues to be a staple in Keith’s live performances and a favorite at country music festivals. For many, it represents a bygone era of country music—one where songs were built on strong melodies, relatable storytelling, and a deep appreciation for tradition. Whether you’re hearing it for the first time or the hundredth, Should’ve Been a Cowboy captures the timeless allure of the cowboy dream, reminding us all of a world where the horizon stretches endlessly, adventure awaits, and anything feels possible.
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Lyrics
I bet you’ve never heard ol’ Marshal Dillon say
Miss Kitty, have you ever thought of runnin’ away?
Settlin’ down, would you marry me
If I asked you twice and begged you, pretty please?
She’d have said, “Yes”, in a New York minute
They never tied the knot, his heart wasn’t in it
He just stole a kiss as he rode away
He never hung his hat up at Kitty’s place
I should’ve been a cowboy
I should’ve learned to rope and ride
Wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy
I might of had a sidekick with a funny name
Runnin’ wild through the hills chasin’ Jesse James
Ending up on the brink of danger
Ridin’ shotgun for the Texas Rangers
Go west young man, haven’t you been told?
California’s full of whiskey, women and gold
Sleepin’ out all night beneath the desert stars
With a dream in my eye and a prayer in my heart
I should’ve been a cowboy
I should’ve learned to rope and ride
Wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy
I should’ve been a cowboy
I should’ve learned to rope and ride
I’d be wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy
Yeah, I should’ve been a cowboy
I should’ve been a cowboy
