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Introduction
Some songs feel like memories you didnβt personally liveβbut somehow still miss. βShouldβve Been a Cowboyβ is one of those songs. When Toby Keith sings it, heβs not just telling a story. Heβs tapping into a shared daydreamβthe urge to trade modern life for wide-open spaces, clear rules, and a little more grit.
What makes this song special is how effortlessly it blends nostalgia with honesty. It isnβt about pretending the past was perfect. Itβs about longing for the idea of itβthe freedom, the courage, the sense that a man stood for something and meant it. Toby delivers the song with warmth and confidence, letting listeners feel like theyβre riding shotgun through an American myth that still matters.
Thereβs a reason this song became an anthem. It speaks to anyone whoβs ever felt out of place in their own time. Anyone whoβs looked at the world and thought, maybe I was born a little too late. Toby doesnβt romanticize escapeβhe celebrates identity. Cowboys, after all, arenβt just about horses and hats. Theyβre about independence, loyalty, and standing tall when the road gets rough.
Listening to Shouldβve Been a Cowboy feels like leaning back and smiling at who you mightβve been. And maybe more importantly, it reminds you that the spirit of that cowboyβthe one who believes in freedom and living on his own termsβdoesnβt belong to the past. Itβs still here. You just have to remember it.
Video
Lyrics
I bet youβve never heard olβ Marshal Dillon say
Miss Kitty, have you ever thought of runninβ away?
Settlinβ down, would you marry me
If I asked you twice and begged you, pretty please?
Sheβd have said, βYesβ, in a New York minute
They never tied the knot, his heart wasnβt in it
He just stole a kiss as he rode away
He never hung his hat up at Kittyβs place
I shouldβve been a cowboy
I shouldβve learned to rope and ride
Wearinβ my six-shooter, ridinβ my pony on a cattle drive
Stealinβ the young girlsβ hearts
Just like Gene and Roy
Singinβ those campfire songs
Woah, I shouldβve been a cowboy
I might of had a sidekick with a funny name
Runninβ wild through the hills chasinβ Jesse James
Ending up on the brink of danger
Ridinβ shotgun for the Texas Rangers
Go west young man, havenβt you been told?
Californiaβs full of whiskey, women and gold
Sleepinβ out all night beneath the desert stars
With a dream in my eye and a prayer in my heart
I shouldβve been a cowboy
I shouldβve learned to rope and ride
Wearinβ my six-shooter, ridinβ my pony on a cattle drive
Stealinβ the young girlsβ hearts
Just like Gene and Roy
Singinβ those campfire songs
Woah, I shouldβve been a cowboy
I shouldβve been a cowboy
I shouldβve learned to rope and ride
Iβd be wearinβ my six-shooter, ridinβ my pony on a cattle drive
Stealinβ the young girlsβ hearts
Just like Gene and Roy
Singinβ those campfire songs
Woah, I shouldβve been a cowboy
Yeah, I shouldβve been a cowboy
I shouldβve been a cowboy