On February 12, 1993, Toby Keith released “Should’ve Been a Cowboy” as his debut single and the first from his self-titled debut album. A few months later, the song already reached the summit of Billboard’s Hot Country Songs chart and the Canadian RPM Country Tracks chart. It even had a minor crossover success, peaking at No. 93 on Billboard Hot 100.
But even more impressive is how “Should’ve Been a Cowboy” rocked the airwaves on country radio. It actually received over three million spins and earned the title of the most-played country song throughout the 1990s.
This song has also become a staple at Oklahoma State University after sporting events. It’s a regular on the PA system, blasting several times as fans stream out of the stadium or arena.
Meaning Behind The Song
Written by Toby Keith, “Should’ve Been a Cowboy” paints a dreamy picture of cowboy life. The man in the song draws inspiration from classic Western movies and their iconic themes. That includes the American radio and television Western drama series Gunsmoke, where the legendary Marshal Dillon never quite found his way to settling down with Miss Kitty, his love interest.
In the catchy chorus, the song tips its hat to the legendary singing cowboys Gene Autry and Roy Rogers. It also mentions classic Western themes like six-shooters (those iconic revolvers) and the thrilling cattle drives you often see in cowboy movies.
All these references are presented as the man spins a tale of his own cowboy escapades. He dreams of having a quirky sidekick similar to iconic characters like Tonto or Gordito, journeying westward to California – echoing the famous phrase “Go West, young man.” He dreams of tracking down notorious outlaw Jesse James, riding alongside the Texas Rangers, and living out all those classic Wild West adventures.
Well, get ready for a wild ride through the cowboy life! Hit play below and dive into Toby Keith’s “Should’ve Been a Cowboy” – the ultimate anthem for that adventurous spirit!”