About the Song
In the spring of 1993, an unknown Oklahoma singer named Toby Keith released a debut single that would forever alter the course of his life and the sound of 1990s country music. That song was “Should’ve Been a Cowboy,” and with it, a country legend was born.
Written by Toby himself, “Should’ve Been a Cowboy” was released as the lead single from his self-titled debut album. At the time, Keith was just a former oil-field roughneck and semi-pro football player with big dreams and a handful of original songs. But when country radio stations picked up the track, it exploded with a force no one could have predicted.
“I bet you’ve never heard ole Marshall Dillon say / Miss Kitty, have you ever thought of runnin’ away?”
Those opening lyrics, nostalgic and clever, captured the imagination of listeners who longed for the romanticism of the Old West. But it was more than just a cowboy fantasy—it was a declaration of identity from a man who would go on to blend traditional country storytelling with rugged independence and modern swagger.
By the end of 1993, “Should’ve Been a Cowboy” had reached No. 1 on the Billboard Hot Country Songs chart and would become the most-played country song of the entire decade—racking up over 3 million spins on radio. It wasn’t just a hit—it was a phenomenon, instantly turning Toby Keith into a household name.
For Toby, that song wasn’t just a breakout single. It was the spark that lit a career defined by grit, patriotism, humor, and unapologetic authenticity. It paved the way for a string of hits like “How Do You Like Me Now?,” “Courtesy of the Red, White and Blue,” and “American Soldier,” cementing him as one of the most influential country artists of his generation.
“I remember hearing it on the radio for the first time,” Toby would later recall. “That’s the moment I knew everything had changed.”
And it had. From rodeos to arenas, from small-town bars to national headlines, Toby Keith’s journey began with just one song—a cowboy’s wish, a catchy hook, and a bold new voice that country music couldn’t ignore.
More than 30 years later, “Should’ve Been a Cowboy” still rides high—proof that legends aren’t always born… sometimes, they’re written one verse at a time.