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.

With exciting instruments, great vocals and a lively stage presence, Flatland Cavalry charms Ann Arbor with their Texan roots ...

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 ...

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 ...