🎵 Song Information

  • Title: Should’ve Been a Cowboy

  • Artist: Toby Keith

  • Writer: Toby Keith

  • Album: Toby Keith (self-titled debut album)

  • Release Date: February 12, 1993

  • Genre: Country

  • Label: Mercury Records

  • Chart Performance: Reached #1 on the Billboard Hot Country Songs chart

  • Certification: RIAA Platinum (2023)

“Should’ve Been a Cowboy” was Toby Keith’s debut single, launching a long and legendary career in country music. It quickly became an anthem of American country identity, with a nostalgic yearning for the Wild West and cowboy freedom. It’s often cited as one of the most-played country songs of the 1990s.


🎯 Song Meaning and Content

“Should’ve Been a Cowboy” tells the story of a man fantasizing about living the adventurous life of an old-school cowboy. Inspired by a moment of rejection at a bar, the narrator imagines himself in a world of shootouts, horseback riding, and romantic adventures — just like the cowboys in old Western movies.

The lyrics are rich with imagery: the dusty trail, riding off into the sunset, chasing outlaws, and wooing saloon girls. Keith cleverly weaves in references to historical and fictional figures like Gene Autry and Roy Rogers, capturing the spirit of the American frontier.

But beyond the surface, the song taps into a universal desire: the wish to break free from modern routine and live boldly, on one’s own terms. It’s a romanticized escape, where the cowboy becomes a symbol of independence, masculinity, and freedom.

With its catchy hook and sing-along chorus, “Should’ve Been a Cowboy” evokes both humor and heartfelt nostalgia — an irresistible combination that made it a favorite among fans for decades.


💭 Deeper Insight: Why the Cowboy Fantasy Still Resonates

At first glance, “Should’ve Been a Cowboy” seems like a lighthearted tribute to old Western movies. But beneath the boots and bravado lies a poignant commentary on identity and longing. The cowboy is more than just a character — he represents a life unchained by corporate jobs, heartbreak, or social expectations.

When Toby Keith released this song in 1993, America was shifting — from the rural to the urban, from individualism to conformity. The cowboy fantasy embodied a rebellion against those changes. It’s the same reason the Wild West continues to appear in pop culture: it offers a timeless, romantic alternative to everyday life.

Keith’s lyrics, humorous and wistful at once, reflect how many people — especially men — quietly dream of being something bigger, wilder, more free. They dream of honor, of protecting others, of exploring open land. And yet they live in cities, wear suits, and carry briefcases.

“Should’ve Been a Cowboy” taps into that unfulfilled wish with charm, catchy melodies, and a wink of nostalgia. In doing so, it became not just a song — but a cultural mirror for anyone who’s ever looked at their life and quietly thought: I should’ve been someone else.


📺 Watch the Song Here:

👉 https://www.youtube.com/watch?v=aIq1LvzSLsk


🎼 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