Should’ve Been a Cowboy was released on Feb. 12, 1993, as Keith’s debut single on his debut album, also titled Should’ve Been a Cowboy. It debuted at #69 before rapidly climbing the chart and hitting #1 on June 5, 1993.
The track is penned independently by Keith and paints a picture of his dreams of being a cowboy. The wistful song laments on how Keith wishes he would have simply been a cowboy instead of living his seemingly boring life with the chorus singing,
“I should’ve been a cowboy
I should’ve learned to rope and ride
Wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy”
The midtempo track is filled with allusions to famous Westerns, outlaws and actors. Marshall Dillon from Gunsmoke, Jesse James, Gene Autry and Roy Rogers are all featured throughout the song’s lyrics.
Should’ve Been a Cowboy has left a lasting legacy on the world of country music. The smash hit has racked up over three million spins on country radio, making it the most-played song on country radio in the 1990s.
Listen to it here: