About the song
There are certain songs that don’t just launch a career—they etch themselves into the very fabric of American popular culture. Toby Keith’s “Should’ve Been a Cowboy” is one such anthem. Released in 1993 as the debut single from his self-titled album, the track marked the beginning of a remarkable run for Keith, who would go on to become one of the most successful and enduring figures in modern country music. But even now, more than three decades later, it’s this early gem—both wistful and rowdy—that continues to hold a special place in the hearts of country fans.
“Should’ve Been a Cowboy” is, at its core, a romanticized tribute to the mythos of the American West. With a blend of nostalgia and longing, Keith sings of missed chances and youthful dreams unfulfilled, imagining himself in the boots of legendary cowboys like Gene Autry, Roy Rogers, and the fictional Marshall Dillon. The lyrics tap into a collective cultural memory—one shaped as much by Western films and television as by actual frontier history—where notions of freedom, rugged independence, and chivalry remain irresistible.
The song’s success was immediate and far-reaching. It soared to the top of the Billboard Hot Country Songs chart, becoming the most-played country song of the 1990s, according to Broadcast Music, Inc. Its appeal crossed generational lines—equally at home on jukeboxes in small-town bars and blaring from the radios of pickup trucks across the heartland. There’s something undeniably catchy in the song’s straightforward structure, infectious chorus, and the bright, soaring twang of its guitar lines that evoke endless prairies and open skies.
But it wasn’t just the melody that stuck. Keith’s voice—then fresh, unpolished, and full of character—lent an authenticity to the sentiment. He wasn’t simply playing cowboy; he sounded like someone who had grown up dreaming of one day saddling a horse and riding off into the sunset. That resonance made the song more than just a radio hit; it became a kind of cultural shorthand for unfulfilled dreams and simpler times, a modern-day cowboy lament dressed in catchy, radio-ready packaging.
In hindsight, “Should’ve Been a Cowboy” not only introduced Toby Keith as a formidable new voice in country music—it encapsulated an entire generation’s longing for a bygone ideal. It’s a song about what might have been, told with a wink, a swagger, and a deep-seated love for the American West that never really fades.
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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
