The song is “Should’ve Been a Cowboy,” and the title is the punchline. Toby Keith didn’t make it up. A buddy of his said it in a Kansas saloon, at the expense of a friend who had just been turned down on the dance floor. Keith wrote the song that same night, and it became the most-played country song of the 1990s.
A Night in Dodge City
Before he was a star, Keith went on a pheasant hunting trip with friends to Dodge City, Kansas, the town made famous by Gunsmoke. As he later told the story, they ended up at a saloon he believed was either the Long Branch or Miss Kitty’s, and the old TV western was already on his mind.
One of the group was a highway patrolman named John, around 45 to 50 years old. He walked over and asked a woman of about 25 to dance. She said no. John came back to the table and reported that she didn’t dance.
A little later, a young cowboy came through the door. He asked her, and she danced with him. That was when one of Keith’s friends leaned over and told John he guessed he should’ve been a cowboy.
Twenty Minutes in a Hotel Bathroom
Keith went back to the hotel and wrote the song that night. By his own account, the whole thing took about 20 minutes. One version of the story says he wrote it in the bathroom so he wouldn’t wake his roommate, Freddie Cortez.
He wrote it alone, and he leaned straight into the Gunsmoke fantasy that had been in the air that night. The finished song opens with a nod to Marshal Dillon and Miss Kitty, then imagines the cowboy life the singer missed out on.
A Demo Tape on an Airplane
Keith was still an unknown Oklahoma singer at the time. According to Country Universe, a fan who worked as a flight attendant passed his demo tape to Nashville producer Harold Shedd. Shedd liked what he heard, went to see Keith perform, and signed him to Mercury Records.
Mercury introduced Keith as part of a “Triple Play” campaign that launched three new artists at once. One of the others was a young Canadian named Shania Twain, whose first singles struggled. Keith’s did not.
Straight to No. 1
“Should’ve Been a Cowboy” was released on February 12, 1993, as Keith’s first single. On June 5, 1993, it reached No. 1 on Billboard’s Hot Country Songs chart and stayed there for two weeks. It also went to No. 1 in Canada and even crossed onto the Hot 100.
Keith first heard himself on the radio in Bowling Green, Kentucky, on the way to a show. By the end of the decade, the Songwriters Hall of Fame says, the song had been played on the radio more than three million times, more than any other country song of the 1990s. It was later certified four-times platinum.
The Song He Never Retired
Keith went on to write and sing dozens of hits, but he never left this one out of his show. It was still on the setlist at his final concert, on December 14, 2023.
Toby Keith died of stomach cancer on February 5, 2024. In the weeks after, “Should’ve Been a Cowboy” climbed back onto Billboard’s country chart, reaching No. 12, more than 30 years after it first came out.
Not bad for a song that began with one man getting turned down for a dance, and another making a joke about it.