Toby Keith’s First No. 1 Hit, ‘Should’ve Been A Cowboy’, Romanticizes Cowboy Life

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Toby Keith started working his way toward a career in music by playing bars and clubs around his home state as a hobby, but when his aspirations as a football player fell through, he moved to Nashville to pursue music full-time. When he couldn’t gain attention from the record labels, he returned home in poor spirits. 

With a stroke of luck, a flight attendant gave his demo to a passenger who happened to be Mercury Records executive, Harold Shedd. Enjoying what he heard, Shedd went to hear Toby perform live and then issued him a recording contract. 

That very first relationship would prove to be a successful venture for both parties when they released his debut single, “Should’ve Been A Cowboy” in early 1993. The song hit the No. 1 spot on Billboard’s U.S. Hot Country Singles chart and the album it came from was certified platinum by the RIAA. 

The song bring forward dreamy fantasies from a man wishing he had been an old Western cowboy. They reference famed films like Gunsmoke, historical quotes, outlaws like Jessie James, and antiqued guns. Written by Toby Keith himself, the song was a success in more than one way for the newly-minted country star. 

Receiving more than 3 million plays on country radio after its release, it became the most-played country song of the decade! 

Watch Toby Keith’s breakout hit in the video below!