The Humiliating Barroom Rejection That Birthed Toby Keith’s “Should’ve Been A Cowboy”

Shoulda learned to rope and ride…

Everybody knows one of Toby Keith‘s biggest hits, his debut single “Should’ve Been A Cowboy.” But did you know it was inspired by a real-life experience of watching one of his friends get rejected at a bar?

The song glamorizing the western lifestyle pays tribute to the many heroes of the wild west, both real and fictional, from Gunsmoke characters Miss Kitty and Marshal Matt Dillon to notorious outlaw Jesse James, and of course singing cowboys and actors Gene Autry and Roy Rogers.

It was released as Toby’s debut single from his self-titled debut album on February 12, 1993, and Toby said in a 2018 interview with Billboard that even in the studio he knew it was going to be a hit:

“When they put that western baritone guitar on there, that’s when magic happened in the studio,” Keith says. “The session guys in the studio were going, ‘This song is a big hit.’ That’s what you want for your first one. I knew the second they put that guitar part on that it was going to be a single, but after a couple days, I was getting feedback from everyone that it was going to be a big hit.”

He was right: The song would go on to become Toby’s first #1 hit on June 5, 1993, and has since been certified 3x platinum by the RIAA (meaning it’s sold over 3 million units).

It’s become one of those classic ’90s song, maybe THE classic ’90s country song at this point, one that’s still covered by other artists and a favorite of pretty much every country music fan. After Toby’s death on February 5, 2024, “Should’ve Been A Cowboy” even re-entered the charts and peaked at #12, over 30 years after it was released.

And according to Toby, it was all inspired by watching his buddy get rejected at a bar.

As Toby recalls it, he was in Dodge City, Kansas – the setting for Gunsmoke – and he witnessed a scene that was straight out a western:

“I think we were actually at the Long Branch Saloon or Miss Kitty’s Saloon — it was something to do with Gunsmoke. This highway patrolman who I had met on the trip, his name was John, he jumps up. He was probably 45 or 50 back then, and he runs over to this 25-year-old cowgirl. He was going to show that he could bust a move. She turns him down.

He comes over, and said, ‘She says she doesn’t dance.’

About 15 minutes later, a young cowboy comes in — and off they go on the dance floor. Everybody was making fun of him, and one of the guys said, ‘John, I guess you should have been a cowboy.’”

Tough scene for John.

But the rejection – and the line from his friend – got the wheels turning, and Toby got to writing what would become his signature song. And as it turns out, once he started writing, it didn’t take long to get the whole song done:

“I thought, ‘I betcha never heard Marshal Dillon have any woman problems because Miss Kitty was always knocking his back door down.’ I just started writing it, and it grew into Jesse James riding shotgun, and Gene and Roy. It all happened in about 20 minutes.”

I’m sure John’s ego was a little bruised after getting turned down, but there’s no doubt that Toby ended up being thankful for his friend getting rejected, because it ended up leading to his biggest hit.