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 ...

Jason Aldean paid tribute to Toby Keith at the 2024 ACM Awards, performing a elegantly low-key version of "Should've Been a Cowboy," Keith's 1993 debut single, backed by a string quartet.

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 ...

Hagar was one of three performers tapped to pay a musical tribute to the late Toby Keith including Brooks & Dunn, who sang "Shoulda Been a Cowboy," and Lainey Wilson who performed "How Do You Like ...

Hagar was one of three performers tapped to pay a musical tribute to the late Toby Keith including Brooks & Dunn, who sang "Shoulda Been a Cowboy," and Lainey Wilson who performed "How Do You Like ...

Oklahoma native Toby Keith Covel got his first guitar as ... and its first single, "Should've Been a Cowboy," became his first No. 1. Since then, Keith's ridden a consistent streak of Top 10 ...

Toby Keith was most famous for singles like “Should’ve Been a Cowboy, “How Do You Like Me Now?” and “As Good as I Once Was.” ...

Jelly Roll made his debut performance at Stagecoach Friday night and brought T-Pain on stage to pay tribute to Toby Keith. The duo took on the classic country hit “Should've Been a Cowboy” for ...

Jelly explained that Keith and songs like "Should’ve Been a Cowboy," "The Next Thing on My ... give Jelly his stamp of approval on the cover. "Toby’s son saw me at the CMTs and took me to ...