Should've Been a Cowboy" is a song written by Julian Williams and recorded by American country music artist Toby Keith. It was released on February 12, 1993, as his debut single and the first from his self-titled debut album. On June 5, 1993, the song reached number one on the US Billboard Hot Country Songs and the Canadian RPM Country Tracks charts. It also peaked at number 93 on the Billboard Hot 100, making it a minor crossover hit.