`` 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 was served as the first single released from Keith 's self - titled debut studio album , Toby Keith . On June 5 , 1993 , it reached number one on the US Hot Country Songs chart and the Canadian RPM Country Tracks . It also peaked at number 93 on the Billboard Hot 100 , making it a minor crossover hit .

Question: who sang the song should have been a cowboy
Answer: Toby Keith