On This Day: Toby Keith Releases Debut Single ‘Should’ve Been a Cowboy’ in 1993

by Katie Maloney

Twenty-eight years ago today Toby Keith clinched his first number one hit song with “Should’ve Been A Cowboy.”

The song is about a man reflecting on his life (and lack of success with women) and concluding that he should’ve been a cowboy instead. During the song, Toby sings, “I should’ve been a cowboy. I should’ve learned to rope and ride. Wearin’ my six-shooter, ridin’ my pony on a cattle drive. Stealin’ the young girls’ hearts just like Gene and Roy. Singin’ those campfire songs. Woah, I should’ve been a cowboy.”

“Should’ve Been A Cowboy” spent 32 weeks on the Hot 100 chart and peaked in the number one spot making it Toby’s first number one hit song. Since then, Toby has released 20 studio albums and seven compilation albums. He’s been nominated for seven Grammys, won three CMAs, and won four AMAs. He was even inducted into the Songwriters Hall of Fame in 2015. Undoubtedly, Toby Keith has made a name for himself in country music. And it all started with “Should’ve Been A Cowboy.” So, what’s the story behind the song?

Toby Keith Wrote The Song After Watching His Friend Get Rejected

Who hasn’t been rejected on the dance floor of a steakhouse? Well, Toby Keith’s friend certainly has. According to Toby, he was inspired to write “Should’ve Been a Cowboy” after watching the whole thing go down. During an interview, Toby revealed the details. It all started when he and a group of friends went to dinner after a day of hunting.

“This highway patrolman who I’d met on this trip, his name was John … He jumps up, and he was probably 45 or 50 back then. And he runs over by a 25-year-old cowgirl, and he says he was gonna show how he can bust a move. She turns him down, and then a few minutes later, he comes back and says she don’t dance. So they’re giving him a bunch of steam over it,” said Toby.

A while later, the group spotted the same girl dancing with a young cowboy.

“So that was not quite 15 minutes later, a young cowboy comes in, and off they go on the dance floor. Everybody’s making fun of him. And somebody says, ‘John, I guess you should’ve been a cowboy,'” said Toby.

Toby said that he wrote the song in about 20 minutes.

“I didn’t know what to do with it. So I thought, ‘I betcha never heard Marshall Dillon say he had any woman problems, ’cause Miss Kitty was always knocking his back door down.’ I started writing it, and it grew into Jesse James and riding shotgun and Gene [Autry] and Roy [Rogers]. It all happened in about 20 minutes,” he said.