3S.The porch creaked just like it did the year Toby wrote “Should’ve Been a Cowboy.” Some things age — some things just settle deeper.Toby leaned back with his coffee, watching the sky open like an old song he never stopped humming. The world got louder, but here the rhythm stayed the same: the wind, the quiet, the truth.
“Scroll down to the end of the article to listen to music.”
Introduction
Sometimes the best songs don’t just tell a story — they tap into a dream we all secretly carry. “Should’ve Been a Cowboy” is that kind of song. When Toby Keith released it back in 1993, it wasn’t just a debut single — it was a mission statement. The song hit like a fresh breeze across country radio, galloping straight into the heart of everyone who ever looked out at a sunset and wondered what life would’ve been like if they’d been born in another time.
The magic of this song lies in its spirit. Toby didn’t just write about cowboys — he wrote about freedom. About the longing to trade deadlines for open skies, noise for quiet, crowds for the company of stars. There’s humor in it, sure, but also a hint of truth that hits deeper with age. Because somewhere between the verses, you realize it’s not just about wanting to wear boots and ride horses — it’s about wanting to live by your own rules.
It became an anthem because it feels timeless — simple, honest, and filled with the kind of hope that never really grows old. You can hear that Oklahoma grit in Toby’s voice, that blend of pride and mischief that made him so beloved. And even decades later, when the opening chords play, something inside still stirs — a reminder that maybe we all should’ve been cowboys, at least once in our hearts.
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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
