On this day in 1993, Toby Keith received his first #1 on the Billboard US Hot Country Songs chart with “Should’ve Been A Cowboy”. The track was released as his debut single and was served as the first single released from Keith’s self-titled debut studio album.

The song has since been Certified Gold by the RIAA and has been spun over three million times on country radio, making it the most-played country song of the 1990s.