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.

The "Need a Favor" singer, 39, performed at the Indio, California, country music festival on Friday and delivered a rendition of Keith's "Should've Been a Cowboy" with a surprise guest appearance ...