On this day in 1993, Toby Keith scored his very first #1 song with “Should’ve Been A Cowboy.” The first of his twenty number one  hits, “Should’ve Been A Cowboy” was the lead-off single from Keith’s self-titled debut album Toby Keith. The song would become Certified Gold and with over three million spins on country radio, is the most played country song of the 1990s.