“63 YEARS… AND NOT A SINGLE ONE WASTED.” From the

There are songs that make you think — and then there are songs that make youwish.“Should’ve Been a Cowboy”is one of those rare tracks that taps into a part of us we don’t always say out loud: that quiet longing for a life a little wilder, a little freer, a little more like the stories we grew up dreaming about.

What makes this song so special isn’t just the catchy melody or the imagery of dusty trails and wide-open skies. It’s the way Toby Keith sings it — with this boyish grin in his voice, like he’s letting you in on a daydream he’s carried since childhood. You can almost see him tipping his hat back, imagining himself riding into the sunset, not because he wants to escape life… but because everyone deserves a moment where imagination feels real.

The magic of the song is how relatable it is.You don’t have to be a cowboy fan or even a country music fan to understand the feeling. It’s about all the versions of ourselves we might have been if life had nudged us differently. The adventures we didn’t take. The risks we talked ourselves out of. The dreams we quietly placed on a shelf because adulthood came knocking.

Toby captures that spirit with humor and heart.There’s no bitterness in the lyrics — just a playful nostalgia that reminds you of being younger, when heroes rode horses, not commuter cars, and when dreaming big felt easy. The song lets you step back into that headspace for a few minutes… and honestly, that’s why people still crank it up decades later.

“Should’ve Been a Cowboy” isn’t just a country anthem.It’s a reminder that inside every adult is a kid who once believed the world was wide open — and maybe still does.

I bet you’ve never heard ol’ Marshal Dillon sayMiss Kitty, have you ever thought of runnin’ away?Settlin’ down, would you marry meIf I asked you twice and begged you, pretty please?She’d have said, “Yes”, in a New York minuteThey never tied the knot, his heart wasn’t in itHe just stole a kiss as he rode awayHe never hung his hat up at Kitty’s placeI should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboyI might of had a sidekick with a funny nameRunnin’ wild through the hills chasin’ Jesse JamesEnding up on the brink of dangerRidin’ shotgun for the Texas RangersGo west young man, haven’t you been told?California’s full of whiskey, women and goldSleepin’ out all night beneath the desert starsWith a dream in my eye and a prayer in my heartI should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboyI should’ve been a cowboyI should’ve learned to rope and rideI’d be wearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboyYeah, I should’ve been a cowboyI should’ve been a cowboy