Toby Keith – Should’ve Been a Cowboy

“Should’ve Been a Cowboy” is Toby Keith’s debut single, and it remains one of his most iconic and enduring songs.

Release Date: February 8, 1993

Background and Inspiration

Toby Keith wrote “Should’ve Been a Cowboy” reflecting on the romanticized image of cowboys in American culture. The song captures the nostalgia and longing for the simpler, adventurous life often depicted in Western movies and TV shows. Keith was inspired by the allure of the cowboy lifestyle, which he contrasts with the reality of his own experiences and the modern world.

Lyrics Overview

The lyrics of “Should’ve Been a Cowboy” narrate the story of someone who fantasizes about living the life of a cowboy, filled with freedom, adventure, and romance. The narrator wistfully imagines what life would have been like if he had been a cowboy.

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 minuteThey never tied the knotHis heart wasn’t in it, he just stole a kiss as he rode awayHe never hung his hat up at Kitty’s place
I should’ve been a cowboy, I should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ a young girl’s heart, just like Gene and RoySingin’ those campfire songs, oh, I should’ve been a cowboy
I might’ve had a sidekick with a funny nameRunning wild through the hills chasing Jesse JamesEnding up on the brink of dangerRiding shotgun for the Texas Rangers
Go west, young man, haven’t you been told?California’s full of whiskey, women and goldSleepin’ out all night ‘neath the desert starsWith a dream in my eye and a prayer in my heart
I should’ve been a cowboy, I should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ a young girl’s heart, just like Gene and RoySingin’ those campfire songs, oh, I should’ve been a cowboy
I should’ve been a cowboy, I should’ve learned to rope and rideI’d be wearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ a young girl’s heart, just like Gene and RoySingin’ those campfire songs, oh, I should’ve been a cowboyYeah, I should’ve been a cowboyI should’ve been a cowboy

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