Remember When Toby Keith Released His Debut Single?

Toby Keith came out of the gate swinging with his 1993 debut single, “Should’ve Been a Cowboy,” a story song that spent two weeks atop the Billboard Hot Country Songs chart and ultimately claimed its place as a ’90s country classic.

“Should’ve Been a Cowboy” was released on Feb. 12, 1993 as the leading single from Keith’s self-tilted debut album, which dropped about two months later.

Right off the bat, it established what fans would quickly learn were hallmarks of Keith’s career and musical identity. Strong songwriting, throwback values and old-school country traditionalism abound here, with a wistful narrator who wishes he was a little more like the rugged cowboys in his favorite Western films.

Keith wrote the song solo, and sure enough, he was inspired by an old Western aesthetic: Specifically, he told the Boot in 2019, he had the television show Gunsmoke on his mind. After a hunting trip in Kansas, the singer and about 20 of his hunting buddies rolled into a bar/restaurant combo for a bite to eat, and one man from Keith’s party decided to ask a girl in the restaurant if she wanted to dance.

“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,” Keith recounted. “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.”

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

“Should’ve Been a Cowboy” became the first in a long list of successful country hits for Keith, who sent 20 singles to the No. 1 spot at country radio over the course of his career.

This year, 2025, marks 32 years since “Should’ve Been a Cowboy” came out, and this anniversary is bittersweet. It falls just one week after the one-year anniversary of the singer’s death on Feb. 5, 2024, after a bout with stomach cancer that lasted more than two years.

How Did Toby Keith Die?

Keith died on Feb. 5, 2024, at the age of 62.

He had been battling stomach cancer for over two years, a diagnosis he announced to fans in summer 2022. Though he took time off to undergo treatment and rest, he vowed to return to the stage whenever possible. He kept that promise with a series of pop-up shows in Oklahoma, a televised performance of “Don’t Let the Old Man In” at the People’s Choice Country Awards and three sold-out shows in Las Vegas in December.

Keith is survived by Tricia Lucus, his wife of almost 40 years, and their three children, Shelley, Krystal and Stelen. He is also survived by multiple grandchildren and extended family.