About the song
There are few songs that encapsulate the spirit of 1990s country music quite like Toby Keith’s debut single, Should’ve Been A Cowboy. Released in 1993, this track not only marked the arrival of a fresh new voice in the genre but also went on to become one of the most defining anthems of its era. It’s the song that put Keith on the map, setting the stage for a career that would span decades, earning him a reputation as one of country music’s most enduring and outspoken artists.
At its heart, Should’ve Been A Cowboy is an unapologetic homage to the rugged, adventurous spirit of the American West. Keith, both the writer and performer, tapped into a timeless fantasy that has captivated countless dreamers: the allure of being a cowboy. He paints a vivid picture of a life lived on horseback, chasing sunsets, and embodying the freedom and bravery often romanticized in classic Western films. The imagery is instantly evocative, drawing listeners into a world where the rules are simple and life is defined by grit, honor, and the open range.
The song’s opening guitar riff is instantly recognizable, setting the tone with a bright, buoyant melody that carries through the verses. Keith’s baritone voice—warm, robust, and undeniably authentic—delivers the lyrics with a mix of wistfulness and bravado. It’s this juxtaposition of longing and pride that makes the song so relatable. There’s a sense of nostalgia woven into the upbeat tempo, as if Keith himself knows that the cowboy way of life is more myth than reality but can’t help but indulge in its romanticism.
Lyrically, Keith masterfully balances humor and sentiment. He references iconic cowboys of the silver screen—like Gene Autry and Roy Rogers—paying tribute to their indelible influence on American pop culture. The song’s chorus is catchy and confident, with a sing-along quality that made it an instant classic on country radio. It’s no wonder that it became the most-played country song of the 1990s—a remarkable feat for a debut single.
What truly sets Should’ve Been A Cowboy apart is its universal appeal. You don’t have to be from a small town or have grown up with Westerns playing on your television to appreciate its sentiment. There’s a universal longing in the lyrics—a desire to escape the monotony of everyday life and embrace a persona that is both fearless and free. In that sense, Keith tapped into something much larger than himself. He gave voice to a collective yearning, wrapped in the rugged, confident sound of early ’90s country music.
Critics and fans alike have praised the song for its timeless quality. It’s one of those rare tracks that feels just as relevant today as it did upon its release. In concerts and honky-tonk bars, it remains a staple—an anthem of cowboy dreams and country pride. Keith’s success with this single cemented his place in country music history, but more than that, it established him as a storyteller—someone who could take a simple concept and turn it into something profoundly resonant.
Should’ve Been A Cowboy is more than just a song; it’s a tribute to a bygone era and a reminder that some dreams never truly fade away. It’s about missed chances and unfulfilled fantasies, but also about embracing the spirit of adventure—if only in our imagination. Toby Keith captured that sentiment perfectly, reminding us all that somewhere deep down, a part of us will always long to be a cowboy.
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Lyrics
I bet you’ve never heard old Marshal Dillon say
Miss Kitty have you ever thought of running away
Settling down would you marry me
If I ask you twice and beg you pretty please
She’d’ve said, “Yes” in a New York minute
They never tied the knot
His heart wasn’t in it
He stole a kiss as he rode away
He never hung his hat up at Kitty’s placeI should’ve been a cowboy
I should’ve learned to rope and ride
Wearing my six-shooter riding my pony on a cattle drive
Stealing the young girls’ hearts
Just like Gene and Roy
Singing those campfire songs
I should’ve been a cowboyI might have 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 RangersGo west young man, haven’t you been told
California’s full of whiskey, women and gold
Sleeping out all night beneath the desert stars
With a dream in my eye and a prayer in my heartI should’ve been a cowboy
I should’ve learned to rope and ride
Wearing my six-shooter riding my pony on a cattle drive
Stealing the young girls’ hearts
Just like Gene and Roy
Singing those campfire songs
I should’ve been a cowboyI should’ve been a cowboy
I should’ve learned to rope and ride
Wearing my six-shooter riding my pony on a cattle drive
Stealing the young girls’ hearts
Just like Gene and Roy
Singing those campfire songs
I should’ve been a cowboy
I should’ve been a cowboy
I should’ve been a cowboy
I should’ve been a cowboy
