Toby Keith’s ‘Should’ve Been a Cowboy’: Story Behind the Country Legend’s Breakout Hit Song

by Emily Morgan

In 1993, Toby Keith dropped his single, “Should’ve Been a Cowboy,” which became the most-played country song of the era.

In the 90s, country stars such as Garth Brooks and Randy Travis dominated the charts. For Keith, he faced a different kind of adversity. When the Oklahoma native moved to Nashville in hopes of making it, he was met with a long road to stardom. 

After dredging through the trenches of various labels, he connected with listeners in a way that few would accomplish. In 1993, he released his first single that would change it all.

While it only took him a few minutes to write it, Keith proved that the best songs don’t have to be labored over if they have a timeless message. 

His ability to incorporate everything he needed for a hit song is clear as day when you listen. Because of the track, Keith gained a following still loyal nearly three decades later.

Toby Keith’s Story Behind The Single

Keith sat down with The Oklahoman to discuss how he wrote the song while on a hunting trip.

“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.’”

“Should’ve Been a Cowboy” is the song that started it all for Toby Keith. The song stayed close to his heart even after so many years.

“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.”