Young Man’s Voice Stuns Viewers In Passionate ‘Should’ve Been A Cowboy’

Young Man’s Voice Stuns Viewers In Passionate ‘Should’ve Been A Cowboy’ | Classic Country Music | Legendary Stories and Songs Videos

MyJasonstewart / YouTube


Jason Stewart took viewers by storm when the unlikely country boy stunned viewers with his incredible southern twang and amazing singing voice.

Sporting a red “Alabama Crimson Tide” t-shirt, the young man strummed his guitar in a small recording room and jumped right into an incredible performance of Toby Keith‘s hit “Should’ve Been A Cowboy.”


Jason’s powerful voice echoed as he sang, “I bet you’ve never heard ole Marshall Dillon say/ Miss Kitty have you ever thought of running away/ Settling down will you marry me/ If I asked you twice and begged you pretty please.”

He began his performance and while it is a little more mellow than Keith’s original, we thoroughly enjoyed his take on the familiar tune.

It seems this song choice wasn’t a success for Stewart alone, as the song landed Keith with a number one spot on the Billboard charts back in the 90s! The song was a smash hit when he released it on his self-titled album.

You can listen to Jason’s fantastic rendition below!

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