One night in the early ’90s, Toby Keith sat with friends after a show in Dodge City, Kansas. A buddy, watching a cowboy ride away with the girl, laughed and said, “Man, I should’ve been a cowboy.” The room chuckled, but Toby’s songwriter instincts didn’t let it pass. He scribbled the phrase down, hearing already the rhythm and the story it could tell. By 1993, that small moment of barroom banter had grown into “Should’ve Been a Cowboy.” Released as Toby’s debut single, it became the most-played country song of the entire decade, an anthem that captured the longing for freedom, romance, and the rugged spirit of the West. For Toby Keith, it was proof that great songs are born not in boardrooms or bright lights, but in the ordinary moments of life — when a single line of truth sparks into music. And for country music, it was the beginning of a voice that would define a generation.
Introduction If there’s one song that introduced Toby Keith to the world with a wink, a swagger, and a whole lot of charm, it’s “Should’ve Been a Cowboy.” Released in…