Keith rose to fame in the 1990s with songs such as Should've Been a Cowboy which topped the country music chart. He announced in June 2022 that he had been diagnosed with stomach cancer ...
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 ...
To honor Keith, who died in February, the singer performed his classic debut single “Should’ve Been a Cowboy.” Jelly Roll opened his New Year’s Eve set in Nashville’s Bicentennial Park ...
31, closing out his set with a cover of the late singer's hit "Should've Been a Cowboy." Keith died at age 62 in February 2024 following a stomach cancer diagnosis, and Jelly has performed "Should ...