Toby Keith

Which singer did Toby Keith's "Should've Been a Cowboy" more proud?

The singer marked yet another major milestone in her legendary career.

It's by choice.

Toby's a legend!

The Boot counts down country music's best tailgating tunes.

The Boot is looking back at some of the top headlines from the first half of the year.

On June 5, 1993, Keith earned his first No. 1 song on the Hot Country Songs Billboard chart, "Should've Been a Cowboy."

Thank you for your service.

If Roberts can make it through every country legend name-checked in this song, he just might have what it takes to win it all...

It's hard to believe it's been more than a quarter of a century!