"Should've Been a Cowboy" is a song written 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.

It has received more than three million spins on country radio, making it the most-played country song of the 1990s.

The song is a staple following sporting events at Oklahoma State University (home of the Cowboys), often played over the venue's PA system several times in succession as fans emptied the stadium or arena.