Starting with his 1993 debut single, 'Should've Been a Cowboy,' Keith has scored an enormous string of 19 No. 1 hits. He's most closely identified with his blue collar drinking anthems like 'Red ...

Halfway through his 50-minute set, Jelly Roll was joined by T-Pain for their cover of Toby Keith‘s hit song "Should've Been a ...

During the Nashville's Big Bash New Year's Eve special on Tuesday night (Dec. 31), the singer performed Toby Keith's 1993 debut single, "Should've Been a Cowboy" as part of a five-song set that ...