Introduction
Have you ever just sat back and wondered, “What if?” What if you’d taken that other path, the one that seemed a little wilder, a little more adventurous? It’s a universal feeling, that quiet daydream of a different life. For me, no song captures this feeling quite like Toby Keith’s debut hit, “Should’ve Been A Cowboy.”
From the moment it starts, the song isn’t just music; it’s a mini-movie playing in your head. It’s about looking at your life and fantasizing about a simpler, more heroic alternative. Keith taps into that classic, romanticized image of the American cowboy, a figure who lives by his own rules under a wide-open sky. He sings about a love that should have been as straightforward as the one between Western icons Marshal Dillon and Miss Kitty, a sentiment that feels both nostalgic and deeply relatable. Who doesn’t long for a love story with a clear hero?
But it’s the details that truly sell the fantasy. The song paints a vivid picture of a life filled with adventure—riding on a cattle drive, chasing “whiskey, women and gold”, and sleeping under the vast desert stars. It’s a life where your only companion might be your trusty sidekick and the soundtrack is the sound of young girls singing campfire songs. It’s a powerful image of freedom and rugged independence.
At its heart, “Should’ve Been A Cowboy” is about a longing for a life with fewer regrets and more epic stories to tell. It’s not just about being a cowboy; it’s about the idea of being a cowboy. It represents the courage, the freedom, and the simple sense of purpose that we sometimes feel is missing from our modern lives. The song gives us permission to indulge in that fantasy for three minutes, to put on the boots and the hat in our minds and ride off into the sunset.
So, what’s your “Should’ve Been A Cowboy” dream? We all have one, and thanks to Toby Keith, we have the perfect anthem for it.
Video
Lyrics
I bet you never heard ol’ Marshall Dillon say
“Miss Kitty, have you ever thought of runnin’ away?
Settling’ down, would you marry me?
If I ask you twice and beg 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, oh, I should’ve been a cowboy
I might’ve had a sidekick with a funny name
Running wild through the hills chasing Jesse James
Ending up on the brink of danger
Riding 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, oh, 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, oh, I should’ve been a cowboy
Yeah, I should’ve been a cowboy
I should’ve been a cowboy