Toby Keith performs Dallas Cowboys version of 'Should've Been a Cowboy' on MNF

Alexis Simmerman, El Paso Times
·2 min read
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Toby Keith died peacefully last night at age 62 after battling stomach cancer, according to his website and a tweet. Keith was diagnosed in the fall of 2021 and disclosed to the public in June 2022.

As Good as I Once Was: Toby Keith's roots

Before launching his career in music, Keith worked as a roughneck in the oil fields of Oklahoma and played semi-pro football. Keith told the Associated Press in a 2001 interview that he learned good lessons in the booming oil fields, which toughened him up, but also showed him the value of money. When the domestic oil field industry collapsed, Keith had not saved.

“It about broke us,” he said. “So I just learned. I’ve taken care of my money this time.”

He spent a couple of seasons as a defensive end for the Oklahoma City Drillers, a farm team for the now-defunct United States Football League. But he found consistent money playing music with his band throughout the red dirt roadhouse circuit in Oklahoma and Texas.

He eventually made his way to Nashville and was signed by Mercury Records head Harold Shedd, who was a big producer at the time for the hit group Alabama. Under Mercery, Keith released his debut record "Toby Keith," in 1993.

Watch: 'Should've Been a Cowboy' (Dallas Cowboys version)

Although the "Red Solo Cup" singer hailed from Clinton, OK, he was a favorite of the NFL's Dallas Cowboys.

As Keith gained popularity in the 1990s, his favorite football team had won three of four Super Bowls, XXVII, XXVIII and XXX. For the team's 1992 appearance on "Monday Night Football," he took to the field to record a music video for "Should've Been a Cowboy."

The hit song was played 3 million times on radio stations, making it the most-played country song of the 1990s.

Keith's love for the Dallas Cowboys didn't stop when the players left the field. Sports Illustrated reports he became close friends with Cowboys players like fellow native Oklahoman Troy Aikman, and team owner Jerry Jones has cited his “Don’t Let The Old Man In” as a personal inspiration.

This article originally appeared on Austin American-Statesman: Toby Keith performs 'Should've Been a Cowboy' with 90s Dallas Cowboys