"Should've Been a Cowboy" is a song written and recorded by American country music artist Toby Keith. It was released on February 8, 1993 as his debut single, and was served as the first single released from Keith's self-titled debut studio album, Toby Keith. On June 5, 1993, it reached number one on the US Hot Country Songs chart and the Canadian RPM Country Tracks. 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 was formerly 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.

The lyrics romanticize the cowboy lifestyle through references to old Westerns. The first verse references Gunsmoke, in which cowboy hero Marshall Dillon never settled down with love interest Miss Kitty. The second verse tells of his own adventures if the narrator were a cowboy: having "a sidekick with a funny name" (possibly a reference to sidekicks like Tonto or Festus or Gordito), travelling west to California (including the historical quote "Go West, young man"), hunting down Western outlaw Jesse James, joining up with the Texas Rangers, and so on. The chorus refers to famous singing cowboys Gene Autry and Roy Rogers, and lists common patterns depicted in Westerns such as six shooters (revolvers) and cattle drives.

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