Behind the Song: Toby Keith, “Should’ve Been a Cowboy”

The early 1990s country charts were ruled by guys named Garth and Vince and a few others, and Toby Keith wasn’t exactly welcomed with open arms when he rode in to Nashville from the oil fields. He wasn’t as young as the industry liked their new artists to be, and nobody really needed another guy from Oklahoma (which the two aforementioned stars were). It wasn’t long, though, before he connected with radio listeners in a way that few would have thought possible.  

Released at the beginning of 1993, the first single from Keith’s eponymous debut album launched a career that continues to be productive, while most of his peers have all but left the building. “Should’ve Been a Cowboy” became the most played country music song of the 1990s, with millions of spins at country radio.

It only took him a few minutes to write it, a textbook example of how the best songs don’t have to be labored over and edited for weeks on end. Name-checking characters from Gunsmoke and legendary singing movie cowboys like Roy Rogers and Gene Autry, and including everything from six-shooters to cattle drives, Keith expertly incorporated and rhymed everything he needed for a hit song. “Should’ve Been a Cowboy” gained him an audience that is still loyal nearly three decades later.

In 2018 Keith told journalist and blogger Brandy McDonnell of The Oklahoman newspaper how he wrote the song while on a hunting trip with some buddies, and how important the song still is.   

“A guy said to another guy, ‘In all honesty, you should’ve been a cowboy,’ when a girl didn’t dance with him in his hunting clothes. And I thought, ‘Man, that sounds like a song idea,’ and it was all over me. I went back and we were all two hunters to a room, and my roommate . . . went to sleep, and I didn’t want to wake him ‘cause he was hateful when you’d wake him up. I went in the bathroom, shut the door, wrote it down and put it in my bag and went hunting the next day. Came home, revisited it, and said ‘I’m gonna record this song.’”

Everybody wants a “career record,” and Keith got his right out of the gate. “It’s the foundation for me of everything,” he said.

His most recent single “That’s Country, Bro” – playfully mocking the “bro-country” trend – didn’t see the chart action of his earlier years, but he used it to continue to pay tribute to his heroes, name-checking everyone from Willie to Waylon to, once again, Gunsmoke characters. But “Should’ve Been a Cowboy” is the song that started it all, and is obviously close to his heart. 

“I’m giving that song its due. … I’ve never played a show that I didn’t play that song. I’ve probably got 15 or 20 number ones I don’t play, and I’ve probably got 20 or 30 top 10s I don’t play. I do a two-hour show every night, and I play a lot of hits and a lot of number ones. But I’ve never not played that song – no matter what. It’s like my pick of the litter as far as how important it was to changing my life – and a lot of people around me.”