<Table> <Tr> <Td> </Td> <Td> "Should've Been a Cowboy" (1993) </Td> <Td> "He Ain't Worth Missing" (1993) </Td> </Tr> </Table> <Tr> <Td> </Td> <Td> "Should've Been a Cowboy" (1993) </Td> <Td> "He Ain't Worth Missing" (1993) </Td> </Tr> <P> "Should've Been a Cowboy" is a song written and recorded by American country music artist Toby Keith . It was released on February 8, 1993 as his debut single and the first from his self - titled debut album . On June 5, 1993, the song reached number one on the US Billboard Hot Country Songs and the Canadian RPM Country Tracks charts . It also peaked at number 93 on the Billboard Hot 100, making it a minor crossover hit . </P> <P> It has received more than three million spins on country radio, making it the most - played country song of the 1990s . </P>

Who sang i should have been a cowboy