Toby Keith – “Should’ve Been a Cowboy” (1993)

The anthem that saddled up a superstar.

With the release of his debut single in 1993, Toby Keith didn’t just introduce himself to country music — he planted his flag. “Should’ve Been a Cowboy” became an instant classic, galloping its way to No. 1 on the country charts and eventually becoming the most-played country song of the entire 1990s.

Built on a blend of easygoing charm, wistful nostalgia, and a dash of outlaw spirit, the song struck a chord with listeners across generations. Its lyrics romanticize the rugged freedom of cowboy life — the wide-open plains, the tales of Jesse James, the silver-screen heroics of Gene Autry and Roy Rogers. But beneath the boots-and-saddles imagery lies something deeper: a longing for a simpler, freer life, untouched by modern constraints.

It wasn’t just about six-shooters and Stetsons — it was about choosing the open trail over the beaten path.

“I should’ve been a cowboy, I should’ve learned to rope and ride…” — a line as catchy as it is iconic. Whether you’re in a honky-tonk bar or a high school football game, chances are, you’ve heard (and sung) those words.

For Toby Keith, this wasn’t just a hit — it was the start of a decades-spanning career that would define him as one of country’s boldest voices. And for fans, it’s the kind of song that never grows old — a boots-up anthem for dreamers, rebels, and anyone who ever wished they were born a few decades too late.

“Should’ve Been a Cowboy” is more than just a debut single — it’s a country music cornerstone, still echoing across open highways, rodeo arenas, and karaoke nights more than 30 years later.