Songfacts®:

• Toby Keith was never a cowboy, but he was cowboy adjacent, working for a rodeo company before launching his music career. He was born and raised in Oklahoma, where there are lots of cowboys of one sort or another, and also some country singers, most famously Merle Haggard.
  
  In "Should've Been A Cowboy," Keith draws from the Old West cowboys of the previous century, the ones sleeping under the stars with their six-shooters nearby.
• "Should've Been A Cowboy" was Toby Keith's first single, released in February 1993 when he was 31. He spent much of his 20s playing semipro football and working the oil fields in Oklahoma. When he finally landed a record deal, he had plenty of material because he had been writing songs, but he wasn't sure they would land.
  
  He was happily surprised when "Should've Been A Cowboy" rose up the charts, all the way to #1 on the Country tally. He played as many shows as he could, trying to put some money away because he thought it might be his last hit. He could rest a little easier when "Who's That Man," the lead single from his next album, also topped the chart. He went on to have 20 #1 Country hits, most of which he wrote or co-wrote.
• The first verse is a reference to the TV series Gunsmoke, which ran 1955–1975. Marshal Dillon and Miss Kitty are characters in the show who had a complicated relationship. There was clearly an attraction, but rarely the opportunity.
• Marc Ball directed the music video, which is drenched in sepia to evoke the Old West. Toby Keith had an affable look and great acting chops, making him a good fit for music videos.
• As Keith's catalog of hits grew, he had to cycle some out of his setlist to make room for the new ones. "Should've Been A Cowboy," though, he performed at most of his shows throughout his career.