JUST ONE LINE IN A BAR CREATED THE ANTHEM OF AN ENTIRE GENERATION. One quiet night in the early ’90s, Toby Keith lingered with friends after a show in Dodge City, Kansas, the air still thick with dust and laughter. As a cowboy rode off into the dark with a girl on his arm, someone joked, “Man, I should’ve been a cowboy.” The room laughed — but Toby didn’t. He felt the line hit deeper than a punchline. He scribbled it down on a napkin, already hearing boots, horses, and heartbreak in the rhythm. By 1993, that offhand joke had transformed into “Should’ve Been a Cowboy.” It exploded beyond expectations, becoming the most-played country song of the decade. What began as barroom chatter turned into an anthem — and the first thunderclap of a voice that would reshape country music for a generation

Introduction The night it happened wasn’t glamorous. No spotlight. No backstage champagne. Just a worn...