Toby Keith Should’ve Been A CowboyWatch at the source

Should've Been a Cowboy is the debut single by American country artist Toby Keith, released on February 12, 1993, as part of his self-titled debut album. The song nostalgically reflects on the romanticism of the cowboy lifestyle, referencing iconic figures like Gene Autry and Roy Rogers. The accompanying music video, directed by Marc Ball, features Keith performing in various Western settings, emphasizing the song's homage to cowboy culture. The track achieved significant success, reaching number one on the US Billboard Hot Country Songs chart and becoming the most-played country song of the 1990s with over three million spins.