Toby Keith

Should’ve Been a Cowboy—This Friday’s Song

This Friday’s song is “Should’ve Been a Cowboy” by Toby Keith. This song was Keith’s debut single in 1993. I have a lot of Toby Keith’s music on my playlists, but this seemed like the right one for this Friday’s song. I was living in Dallas helping to bring a new company to life when this song was released. It was really hard and amazingly fun. The song evoked the brash, risk-taking style you needed to stay focused and overcome the odds. Hope you enjoy!

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