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 ...

To honor Keith, who died in February, the singer performed his classic debut single “Should’ve Been a Cowboy.” Jelly Roll opened his New Year’s Eve set in Nashville’s Bicentennial Park ...

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 ...

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 ...

The 40-year-old country star helped ring in the new year with a five-song performance during Nashville’s Big Bash at the Tennessee capitol's Bicentennial Park on Dec. 31, closing out his set with a ...