Dissecting "Should've Been a Cowboy" by Toby Keith - 1993 episode artwork

EPISODE · Jul 20, 2026 · 20 MIN

Dissecting "Should've Been a Cowboy" by Toby Keith - 1993

from Nashville Anthems: Dissecting 80s & 90s Country Music

We return to a country music icon by taking on his debut single and (at least for the 90s) his signature song: Toby Keith's "Should've Been a Cowboy". Keith struck a chord in 1993 with the mid-20th-century western nostalgia that permeates the lyrics, but how does his specific take on this theme depart from some others we've covered that trod similar ground? And how does that take bring some needed nuance to our understanding of Toby Keith the man and persona, before "How Do You Like Me Now"?

Episode metadata supplied by the publisher feed · Published Jul 20, 2026

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Dissecting "Should've Been a Cowboy" by Toby Keith - 1993

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