Toby Keith (July 8, 1961 – February 5, 2024) was a country music legend, a true patriot, and an American icon. My favorite song of his was “Should’ve Been A Cowboy” from the 1993 album. It would debut as number one on the US Billboard Hot Country Songs and ninety-three on the Billboard Hot 100, making it a crossover hit. If you have not heard it, get out from underneath that rock.

Since its release, it has been a staple on the radio airwaves and at sporting events sealing it as a work of American culture. Because of this, many other artists have done their own version of the song. Here are my top 5 favorite covers of “Should’ve Been A Cowboy.”

American Aquarian

“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…”

Walker McGuire

“Stealin’ the young girls’ hearts. Just like Gene and Roy. Singin’ those campfire songs. Woah, I should’ve been a cowboy”

Brett Westgrove

“I might of had a sidekick with a funny name. Runnin’ wild through the hills chasin’ Jesse James. Ending up on the brink of danger. Ridin’ shotgun for the Texas Rangers.”

Bryce Mauldin

“Go west young man, haven’t you been told? California’s full of whiskey, women and gold.”

Kitchen Dwellers and Daniel Donato

“Woah, I should’ve been a Cowboy.”

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