TOBY KEITH’S REAL COWBOY DAYS: MORE THAN JUST A SONG TITLE Here’s the hook: when Toby Keith sang “Should’ve Been a Cowboy,” he wasn’t just dreaming — he had actually lived part of that life as a teenager. Long before he became a country music superstar, young Toby worked as a rodeo hand on an Oklahoma farm during his high school years. He told the Tulsa World, “We fed, watered and attended to all the stock the owner had, and a couple of times a week he’d bring back a bunch of bulls from the bull sales. He’d put ’em in an arena, and we’d all jump in there to see whether they’d buck or not. We’d ride ’em for five or six days, and whichever one kept bucking, he’d take it and try it in a rodeo.” Keith was humble about this experience, describing himself as “basically just a farm boy, a country boy who had some experience with cowboys and rodeos as a teenager.” He believed being a cowboy was once a skilled trade, but had become mostly “dress-up” in modern times. This authentic background gave his cowboy songs genuine weight that audiences could feel. What’s even more surprising is the unexpected path he took next — one that almost led him away from music entirely.
Toby Keith’s Real Cowboy Days: More Than Just a Song Title When Toby Keith sang “Should’ve Been a Cowboy,” millions…