Toby Keith Wrote “Should’ve Been A Cowboy” In 20 Minutes After A Hunting Buddy Was Rejected At A Bar

Toby Keith country music
Toby Keith

The backstory to one of the most iconic country music songs.

“Should’ve Been A Cowboy,” written and recorded by Toby Keith in 1993, appeared on his self-titled album and is arguably one of the most well-known songs out of his catalog. With the song charting on the American and Canadian country charts and the all-genre charts, “Should’ve Been A Cowboy” was a significant crossover hit.

Aside from the chart success of the single, it also dominated the radio in the ’90s with over three million spins.

The song lyrics are catchy and pose the story of a man who wishes he could have lived out his dreams of living in the Wild West as a cowpoke, but they never come true. And while some songs just come out of the imagination, Toby Keith opened up about what led him to write the single as part of his 100% Songwriter promotion.

The Moore, Oklahoma native shares the story of how he and 20 of his buddies were on a hunting trip, and the events of that trip inspired the lyrics we all know and love today.

“I was still trying to finish up my first album, and I went on a pheasant hunting trip to Dodge City, Kansas, with about 20 knuckleheads. We got up there, and the town was staged for the old ‘Gunsmoke’ series, so it was intriguing to know that we were in a historic old west town. So I thought of ‘Gunsmoke’… that was on my mind. 

Then, there was a guy that got up at our table and tried to dance with this girl in this steak house bar we were eating in… we were in hunting clothes. His name was John. He jumped up in his hunting clothes and ran over to grab this cowgirl to dance, and she turned him down. And on this way back to the table, we were laughing, and one of the guys hollers, “John, you should’ve been a cowboy.”  

So I thought, I’m going to write that. I took my guitar, sat on the side of the motel tub, and shut the door so no one could hear me. I didn’t want to wake anyone up because we had an early hunt, and I wrote it in about 20 minutes.”

It’s always funny to me how some of country music’s biggest hits are often songs inspired by a funny backstory and take less than an hour for the writer to crank out.

Thank goodness for Keith’s hunting friend getting turned down at that steakhouse in the old western town because it led to one of the best songs from Toby Keith.

Turn this classic all the way up.

A beer bottle on a dock

STAY ENTERTAINED

A RIFF ON WHAT COUNTRY IS REALLY ABOUT

A beer bottle on a dock