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.

"Should've Been a Cowboy": This breakout hit became a defining anthem for the '90s generation, showcasing his storytelling prowess. "Courtesy of the Red, White and Blue (The Angry American)": Released ...

At the Ryman Auditorium in Nashville, often called the "Mother Church of Country Music”, ERNESTlit up the stage in a moment designed to bridge past and present country vibes. Decked out with a guitar ...

Toby Keith ruled the country music airwaves in the ’90s, starting with his 1993 debut single “Should’ve Been a Cowboy.” Throughout his three-decade career, the “Big Dog Daddy” sent 65 of 70 singles to ...

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 ...

The beloved country singer died at age 62 on Feb. 5, 2024.

The larger-than-life country music singer Toby Keith, known for his patriotic swagger, died on Monday at the age of 62. The “Beer For My Horses” singer-songwriter had been battling stomach cancer ...

Two years ago today, the country music world lost a larger-than-life superstar who got his start with a string of '90s hits.

On February 5, 2026, country music fans around the world are pausing to remember the legendary Toby Keith, who passed away at the age of 62 following a courageous two-year battle with stomach cancer.

Jackson Dean stopped by Taste of Country Nights to share some special Toby Keith memories that nearly brought us to tears. Host Evan Paul asked Dean what it was like opening shows for Keith before he ...