About the song
Toby Keith’s 1993 debut single, “Should’ve Been a Cowboy,” is more than just a country song—it’s an anthem, a slice of Americana wrapped in melody and nostalgia. When it first hit the airwaves, it didn’t just introduce the world to Keith’s deep, commanding voice and easygoing charm; it set the tone for a career that would span decades. With its blend of wistful longing, cowboy mythology, and traditional country instrumentation, the song resonated deeply with audiences, becoming one of the most-played country songs of the ‘90s.
At its core, “Should’ve Been a Cowboy” is a celebration of the cowboy archetype—a romanticized look at the freedom, adventure, and rugged independence that the image of the cowboy represents. The lyrics paint vivid pictures of wide-open spaces, silver-screen heroes, and a lifestyle unfettered by modern constraints. Keith, in his signature baritone, delivers the story of a man who dreams of a different path—one where he could have roamed the frontier, lived by his own rules, and embodied the spirit of the Wild West. It’s a theme that has long captivated country music fans, tapping into a collective yearning for simpler, wilder times.
Musically, the song is pure ‘90s country, blending honky-tonk twang with smooth radio-ready production. The arrangement is lively yet relaxed, featuring the bright strum of an acoustic guitar, the steady pulse of drums, and a lead electric guitar that punctuates the verses with playful riffs. There’s a warmth to the instrumentation that mirrors the song’s nostalgic sentiment, making it easy to sing along to—an essential quality for any great country hit. Keith’s vocals, rich and full of personality, carry just the right balance of wistfulness and confidence, as if he’s smiling to himself about the life that could have been.
What makes “Should’ve Been a Cowboy” so enduring isn’t just its catchy melody or the charisma in Keith’s delivery; it’s the way it taps into something universal. Almost everyone, at some point, has looked back and wondered about the road not taken. Whether it’s the fantasy of being a cowboy, a musician, an artist, or an explorer, there’s a shared human experience in imagining a different version of oneself. The song doesn’t dwell in regret—it revels in the idea, making it feel more like a joyful daydream than a lament.
Beyond its immediate success—reaching No. 1 on the Billboard Hot Country Songs chart—it has remained a staple of country music, played in honky-tonks, on jukeboxes, and at tailgates across America. It helped define Toby Keith’s image as a proud Oklahoman with a knack for writing songs that feel both personal and universal. In many ways, the song embodies the spirit of ‘90s country itself—rich in storytelling, steeped in tradition, but polished just enough to resonate with a modern audience.
For those who heard it in 1993, the song was an instant classic. And for new listeners discovering it today, it still holds the same charm—proof that some songs never fade, no matter how much time passes.
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Lyrics
I bet you’ve never heard ol’ Marshall Dillion say
Miss Kitty have you ever thought of running away
Settling down would you marry me
If I asked you twice and begged you pretty please
She’d of said yes in a New York minute
They never tied the knot
His heart wasn’t in it
He stole a kiss as he road 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 girl’s heart
Just like Gene and Roy
Singing those campfire songs
Oh I should’ve been a cowboyI might of had a side kick with a funny name
Running wild through the hills chasing Jesse James
Ending up on the brink of danger
Riding shotgun for the Texas Rangers
Go west yound man, haven’t you been told
California’s full of whisky, women and gold
Sleeping out all night beneath the desert stars
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 girl’s hearts
Just like Gene and Roy
Singing those campfire songs
Oh I should’ve been a cowboyI should’ve been a Cowboy
I should’ve learned to rope and ride
I’d be wearing my six-shooter riding my pony on a cattle drive
Stealing the young girl’s hearts
Just like Gene and Roy
Singing those campfire songs
Oh I should’ve been a Cowboy
Yeah I should’ve been a Cowboy
Yeah I should’ve been a Cowboy
