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 ...
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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 ...
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Jelly Roll Pays Tribute to Toby Keith on New Year's Eve With Another Emotional ‘Should've Been a Cowboy' CoverDuring 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 ...
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