32 years ago was a monumental day for Toby Keith. It was on June 5, 1993, when Keith scored his first of many No. 1 singles, with “Should’ve Been a Cowboy.” “Should’ve Been A Cowboy” was the first song released from Keith’s eponymous freshman album. Keith wrote all but two of the songs on the record, penning “Should’ve Been A Cowboy” by himself.
“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,” Keith previously told The Oklahoman. “And I thought, ‘Man, that sounds like a song idea,’ and it was all over me,”
Once Keith had the idea, it didn’t take long for him to bring it to life.
“I went back, and we were all two hunters to a room,” he remembered. “And my roommate was Freddie Cortez. He’s passed away now, but he used to own Chastain’s and a bunch of country bars in town. Freddie 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.'”
Keith’s instincts were usually correct, but he had no idea how much that one song would change everything for him.
“It’s the foundation for me of everything,” he said.
From that point on, until Keith passed away in early 2024, “Should’ve Been A Cowboy” was a mainstay at his shows.
“I’ve never not played that song, no matter what,” Keith said. “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.”
Keith passed away on February 5, 2024, after a brave battle with stomach cancer.
In October, Keith was posthumously inducted into the Country Music Hall of Fame. Randy Owen had the honor of inducting Keith Keith.
“This is about a man that I dearly loved, and I always felt like he dearly loved me, and he truly cared about me,” Owen said. “When we were filming the CMT Giants, I was doing real good, until I went around and saw his name on a dressing room, knowing that he couldn’t be there. That’s how much I felt like he loved me, and the group, Alabama. So I’ll always be thankful to Toby for caring so much. He was absolutely emphatic that he was going to make that taping, even though his health didn’t allow him to … He loved his country, he loved his family. He proved that over and over again.”
Jason Aldean later released his own version of “Should’ve Been A Cowboy,” in tribute to Keith. All of Keith’s music and upcoming shows can be found at TobyKeith.com.