About the Song

Released in 1993, Toby Keith’s “Should’ve Been a Cowboy” didn’t just top the charts, it lassoed the hearts of millions, becoming an iconic anthem for dreamers and free spirits. But the song’s journey began long before its chart-topping success.

Inspired by his own Oklahoma upbringing and love for the Western lifestyle, Keith wrote the lyrics while on tour, strumming his guitar on a bus between gigs. It wasn’t an instant hit. Initially rejected by record labels for being “too country,” Keith’s persistence paid off when it landed on his debut album “Toby Keith.”

The song’s relatable lyrics resonated with listeners. It tells the story of a man stuck in a monotonous office job, yearning for the wide-open spaces and adventurous spirit of a cowboy. Lines like “Concrete jungle where dreams are paved with dust” and “I was born lookin’ out on a horizon line” tapped into a collective desire for freedom and connection to nature.

But “Should’ve Been a Cowboy” wasn’t just about escapism. It celebrated individuality and staying true to oneself, even if it meant going against the grain. The music video, filmed in Monument Valley, Utah, perfectly captured the song’s spirit with its rugged landscapes, horseback riding, and Keith’s charismatic performance.

The song’s success was phenomenal. It reached number one on the Billboard Hot Country Songs chart and stayed there for three weeks, launching Keith’s career into superstardom. It even crossed over to mainstream audiences, winning the Country Music Association award for Single of the Year and earning a Grammy nomination.

Today, “Should’ve Been a Cowboy” remains a timeless classic. It’s a staple at rodeos, country bars, and singalongs across the globe. More than just a song, it’s a cultural touchstone, reminding us to chase our dreams, embrace adventure, and never lose sight of what truly makes us tick. So crank up the volume, put on your boots, and let the spirit of the cowboy take hold.

Video

Lyrics

I bet you’ve never heard ol’ Marshal Dillon sayMiss Kitty, have you ever thought of runnin’ away?Settlin’ down, would you marry meIf I asked you twice and begged you, pretty please?She’d have said, “Yes”, in a New York minuteThey never tied the knot, his heart wasn’t in itHe just stole a kiss as he rode awayHe never hung his hat up at Kitty’s place
I should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboy
I might of had a sidekick with a funny nameRunnin’ wild through the hills chasin’ Jesse JamesEnding up on the brink of dangerRidin’ shotgun for the Texas RangersGo west young man, haven’t you been told?California’s full of whiskey, women and goldSleepin’ out all night beneath the desert starsWith a dream in my eye and a prayer in my heart
I should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboy
I should’ve been a cowboyI should’ve learned to rope and rideI’d be wearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboy
Yeah, I should’ve been a cowboyI should’ve been a cowboy