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 ...

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 ...