90s Country: This Toby Keith Song Was the Most Played Country Song of the Decade

by Josh Lanier

A chance remark about why a girl turned down a dance invite led Toby Keith to write the most played song of the 1990s. In fact, it launched his career.

You’d likely expect the song with the most spins on country radio in the 1990s would be from Garth Brooks, Travis Tritt, or Vince Gill. Instead, it’s actually “You Should Have Been a Cowboy” from Keith’s 1993 eponymous debut album. Keith said he got the inspiration for the song after he saw a woman reject a guy at a bar.

“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,” Keith told a reporter in 2018. “… 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.’”

He said he had fleshed out the concept and had the majority of the song written in 20 minutes. But Keith told Billboard he became obsessed with getting it just right.

“I couldn’t quit working on it. It was one of my favorite things I’ve done in my life,” Keith said. “It wasn’t a challenge as much as it was I knew who I was writing it for, and who had inspired me to write it. … I was a zombie for about two days. The second I wrote it, it was like I jumped about 500 feet in the air. I knew I had accomplished what I wanted to accomplish.”

Toby Keith Still Plays the Song at Every Concert

Toby Keith went on to have one of the biggest careers in country music history. But, he still makes sure to dance with the one who brought him, in a matter of speaking. He said he still performs “You Should Have Been a Cowboy” at every show. Even though there are other songs in his arsenal that have gained relevancy since, it’s a mainstay.

“I’m giving that song its due,” he told the Oklahoman. “… 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.”