About the song
Country music has always been a genre deeply rooted in tradition, storytelling, and heartfelt tribute, and few moments encapsulate that spirit better than Jason Aldean’s stirring performance of “Should’ve Been a Cowboy” at the 59th annual Academy of Country Music Awards. This was no ordinary cover—it was a poignant farewell, a musical salute to the late Toby Keith, a man whose voice, presence, and legacy have left an indelible mark on the country music landscape.
Toby Keith’s “Should’ve Been a Cowboy” is more than just a hit song; it’s an anthem. Released in 1993 as Keith’s debut single, it quickly became one of the most recognizable tracks in modern country, blending nostalgia, rugged independence, and that signature honky-tonk spirit. It spoke to the dreamers, the restless souls who longed for the romance and adventure of the Old West. Over the years, it became synonymous with Keith himself—his swagger, his all-American persona, and his ability to write songs that resonated across generations.
When Jason Aldean took the stage to perform this classic, it wasn’t just about the music—it was about honoring a friend, a mentor, and a legend gone too soon. Aldean, known for his own brand of hard-driving country rock, brought his signature grit to the song while staying true to Keith’s original energy. His performance was filled with reverence, not just in his delivery, but in the way he carried the weight of the moment. This was a heartfelt goodbye from one country star to another, a reminder that while Toby Keith may no longer be with us, his music—and his cowboy spirit—will never fade.
Video
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
