Toby Keith, the late country music superstar, will be represented in the 2025 Kentucky Derby by longshot Render Judgment.

Always willing to support the military, Toby Keith once had to pause his concert with the USO due to a mortar attack.

Toby Keith is a legendary country music artist ... His breakout single, Should’ve Been a Cowboy, launched a career that has since produced numerous chart-topping hits and multi-platinum albums.

Whether it’s a mid-afternoon Coachella set or a final party after a Stagecoach headliner, T-Pain proved that he can fit into ...

Jelly Roll covered one of Toby Keith’s greatest hits in ... star included a rendition of Keith’s “Should’ve Been A Cowboy” during his live performance in Nashville.

“He’s got the vibe.” “He is a cowboy,” hitting coach Chad Mottola concluded. Toby Keith’s classic, “Should’ve Been a Cowboy,” is a fitting soundtrack, but as Misner steps to the ...

Toby Keith’s legacy is ... cover of Keith’s iconic song "Should’ve Been a Cowboy," assisted by T-Pain, released on Amazon Music Originals and performed live at the Stagecoach music festival.

Some of country music's top stars will join forces July 29 at Nashville's Bridgestone Arena for the live charity concert event "Toby Keith ... of hits like “Should’ve Been A Cowboy ...

Toby Keith's life and legacy were celebrated ... guitarists performed an emotional rendition of Keith's 1993 single "Should've Been a Cowboy," that flooded the theater with emotion.