Country Bands | Legendary & Modern Country Music Bands | Wild Country Radio

Toby Keith: Songs, Legacy & Biography

October 29, 2026 2

Big voice, bigger personality. Toby Keith wrote and sang some of the most-played country songs of the ’90s and 2000s, and he never apologized for who he was. He died on February 5, 2024, at 62, after a battle with stomach cancer. Part of our guide to country music artists.

Toby Keith at a glance

Born	July 8, 1961, Clinton, Oklahoma
Died	February 5, 2024
Debut single	“Should’ve Been a Cowboy” (1993), a No. 1
Songwriter	Inducted into the Songwriters Hall of Fame (2015)
Service	Performed on 11 USO tours for U.S. troops
Honors	National Medal of Arts (2021)

The Oklahoma songwriter

Keith worked in the oil fields and played semi-pro football before music took over. His first single, “Should’ve Been a Cowboy”, went to No. 1 and became one of the most-played country songs of the decade.

The hit machine

In the 2000s he wrote and released a steady run of hits, many of them loud, funny and proudly patriotic. He also launched his own label, Show Dog.

Off the stage

Keith played 11 USO tours for troops serving overseas and built OK Kids Korral, a home in Oklahoma City for children with cancer and their families, through the Toby Keith Foundation.

Toby Keith's best songs

“Should’ve Been a Cowboy” – The debut and a standard.
“How Do You Like Me Now?!” – Revenge on a high-school crush.
“I Wanna Talk About Me” – Comedy with a beat.
“Courtesy of the Red, White and Blue (The Angry American)” – Written after September 11.
“Beer for My Horses” (with Willie Nelson) – An outlaw duet.
“I Love This Bar” – A tribute to every regular.
“As Good as I Once Was” – Aging with a grin.
“Red Solo Cup” – Pure party.
“Don’t Let the Old Man In” – A late-career masterpiece.

His place in country history

Keith was one of the defining voices of post-’90s mainstream country. Read more in our history of country music.

If you like Toby Keith

Try Blake Shelton, a fellow Oklahoman, and The Highwaymen, whose outlaw spirit Keith admired.

Toby Keith FAQs

When did Toby Keith die?

February 5, 2024, at age 62, after a battle with stomach cancer.

What was Toby Keith's first hit?

“Should’ve Been a Cowboy” (1993), a No. 1 country single.

Where was Toby Keith from?

Clinton, Oklahoma.

Sources

Toby Keith official site · Songwriters Hall of Fame · Toby Keith Foundation [VERIFY: URL]

How we report: Facts on this page come from the sources listed above and are checked by a second editor. Read our editorial standards. Spot an error? Tell us.