Toby Keith's debut was a self-fulfilling prophecy. Released in 1993, "Should've Been a Cowboy" introduced the world to Keith’s salt-of-the-earth twang and became the most-played country song of that decade, transforming the small-town boy into an all-American icon. Born in 1961 in Oklahoma, Keith earned his workingman’s bona fides long before his big break, sitting in with the band at his grandmother’s nightclub as a kid and toiling in the oil fields as a young adult. After playing the Oklahoma and Texas honky-tonk circuits, he took to Nashville in the early ‘90s, setting himself apart by staying honest and blunt about his values. He pledged allegiance to the flag with the post-9/11 song “Courtesy of the Red, White and Blue (The Angry American),” and sought vigilante justice with Willie Nelson on “Beer for My Horses.” But every cowboy knows how to get loose, too, and Keith’s party jams, like the boozy “Red Solo Cup,” are legion. After battling cancer for nearly two years, Keith died in February 2024 at the age of 62.