About the song
When Toby Keith burst onto the country music scene in the early 1990s, few could have predicted the longevity and impact of his career. But right from the start, he made a statement with his debut single, “Should’ve Been a Cowboy,” released in 1993. It wasn’t just a hit—it became an anthem. With its catchy melody, nostalgic storytelling, and distinctly American themes, this song didn’t just introduce a new artist to the charts—it reminded listeners of a deep and enduring national mythology.
“Should’ve Been a Cowboy” captures a yearning that resonates with many, particularly those who grew up watching Westerns or reading tales of frontier legends. The song plays on that collective memory of cowboys and outlaws, romanticizing the rugged independence of figures like Gene Autry, Roy Rogers, and the Lone Ranger. Toby Keith’s lyrics conjure wide-open plains, horses, six-shooters, and the dream of a simpler, more heroic time—a time when men settled scores at high noon and honor was carried in a holster.
But Keith isn’t just recounting old movie plots. The clever twist in the song is its tone of wistful regret. The narrator isn’t a cowboy—he’s someone who wishes he’d taken that path, who imagines what life could have been like if he’d followed a different road. There’s a certain universality in that sentiment. How many of us have looked back and thought, “I should’ve done that” or “I missed my moment”? Keith taps into that emotion without bitterness, wrapping it instead in charm, humor, and that signature easygoing vocal delivery.
What’s more, the track’s success speaks volumes. It became the most-played country song of the 1990s—a fact that underlines just how much it struck a chord with listeners across America. Whether you were a die-hard country fan or someone who just appreciated a good story well told, “Should’ve Been a Cowboy” was a song that invited you in, poured you a drink, and spun you a yarn.
In the years since, Toby Keith has built a reputation as a no-nonsense, flag-waving voice in country music. But this song, his first, remains a sentimental favorite—a reminder of dreams, legends, and the cowboy spirit that still rides tall in the American imagination.
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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
