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Toby Keith launched his legendary career with his breakout single, “Should’ve Been A Cowboy,” which appeared on the Oklahoma-born country star’s self-titled debut studio album in 1993. The song remains one of Keith’s biggest hits today.
“Before it was a hit (and the most played country song of the 90s), it was just a song Toby shared with his friend [former NFL quarterback Troy Aikman],” reads the caption on the throwback clip that was shared to Keith’s social media accounts on Thursday (October 30).
“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”
Keith “passed peacefully…surrounded by family,” on February 5, 2024, following a battle with stomach cancer that he fought “with grace and courage,” per a statement released when the singer-songwriter died. He was 62. He is survived by his wife, Tricia Covel, daughters Shelley Covel Rowland and Krystal Keith, son Stelen Keith Covel, and grandchildren. On February 5, 2025, a tribute read, in part, “today we hope you will celebrate and listen to his music with us, where we know he is smiling down and raising his cup. A toast to a life well lived.”
Watch Keith’s rendition of “Should’ve Ben A Cowboy” before it was a hit here: