Toby Keith Celebrates Debut Single “Should’ve Been A Cowboy” 25 Years After Release

Toby Keith Should've Been a cowboy 25 years
Photos by Tammie Arroyo/

It’s hard to believe it’s been 25 years since Toby Keith hit the country music scene with his debut single “Should’ve Been a Cowboy.” But sure enough, the platinum selling singer was celebrated on Wednesday (Dec. 5) at BMI in Nashville for that milestone anniversary.

Toby was surrounded by his family and friends, former Pittsburgh Steelers quarterback Terry Bradshaw, producer/executive Harold Shedd, his wife Trisha and daughters Shelley and Krystal with their families, to receive a special citation of appreciation.

The citation was in recognition of Toby’s outstanding contributions to the world of country music and 25 years of success of his No. 1 single “Should’ve Been a Cowboy.”

The Oklahoma native burst onto the country music scene in 1993 with a song that had a 32-year-old Toby singing about wishing he had been a cowboy just like Gene Autry and Roy Rogers.

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,” he sang in the chorus.

The hit song was featured on his self-titled debut album, which included future hits such as, A Little Less Talk and A Lot More Action,” “He Ain’t Worth Missing” and “Wish I Didn’t Know Now.”

Twenty five years later, the 57-year-old singer has accumulated numerous awards including AMA, CMA and ACM awards as well as Billboard’s Artist of the Decade. Toby branched out into the acting world with several television appearances and film roles including, Beer for My Horses and Broken Bridges.

Congratulations Toby! Here’s to 25 more!

Toby Keith Milestone Should've been a cowboy
Photos by Tammie Arroyo/

Toby Keith Milestone Should've been a cowboy

Toby Keith Milestone Should've been a cowboy