"Should've Been a Cowboy" is a song written and recorded by 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 #1 on the US Billboard Hot Country Songs and the Canadian RPM Country Tracks charts. It also peaked at #93 on the Billboard Hot 100, making it a minor crossover hit. The song is a staple following sporting events at Oklahoma State University (home of the Cowboys)

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