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.

We have the story behind the first single Toby Keith released, "Should've Been A Cowboy", which also became his first No. 1 hit.

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 ...

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.

Toby Keith’s “Should’ve Been A Cowboy Tour XXV presented by Ford F-Series” will stop at the Seneca Allegany Casino at 8 p.m. Friday, Aug. 24, with special guest Trace Adkins. Submitted photo SALAMANCA ...

Add Yahoo as a preferred source to see more of our stories on Google. Country music legend Toby Keith, who died in February 2024 at age 62 after a two-year battle with stomach cancer, has been honored ...

This marked the start of a lifelong friendship with the “On the Road Again” star, as Floyd and his sister Jill spent the next ...

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 ...