Over the years, “Should’ve Been a Cowboy” earned more than three million spins on country radio, making it the most-played country song of the 1990s.

But like... what else could it have been? It's iconic. Toby Keith left a legendary mark on country music, and he came out of the gate swinging with his first hit "Should've Been A Cowboy." And on this ...

In country songs, there's nothing quite like a good cowboy anthem. The boots, the dust, the wide open skies—it's all wrapped up in a sound that feels rugged and timeless. At Drummond Ranch, cowboy ...

We love 1990s country music, but we have to ask about these three classics, because they might be played just a little too much.

"Should've Have Been a Cowboy" was first recorded in 1992 and released as a single the following year. It was a solo write ...

In Defense of Drinking finds the South Dakota native singing about bad decisions in Texas and good times in the beer garden ...