“One night in the early ’90s, after a show in Dodge City, Kansas, Toby Keith sat with friends swapping stories. As they watched a cowboy ride off with the girl, one buddy laughed, “Man, I should’ve been a cowboy.” The line drew chuckles from the group, but Toby’s songwriter’s ear caught fire. He jotted it down, already hearing the rhythm and the tale it could unfold. By 1993, that casual bit of barroom banter had transformed into “Should’ve Been a Cowboy.” Released as his debut single, it didn’t just launch a career — it became the most-played country song of the decade. The anthem spoke to the yearning for open skies, freedom, romance, and the rugged heart of the West. For Toby Keith, it was proof that the best songs are born not from boardrooms or bright lights, but from everyday truths — the kind you almost laugh past. For country music, it marked the arrival of a voice destined to define a generation.”
Introduction One summer afternoon in 2002, while sitting on his porch in Oklahoma, Toby Keith found himself strumming his guitar and humming…