Toby Keith Reflects on the 25th Anniversary of His Breakthrough Hit, 'Should've Been a Cowboy'

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Toby Keith performs onstage at day 1 of the 2013 Stagecoach California's Country Music Festival at The Empire Polo Field on April 26, 2013 in Indio, Calif.

Toby Keith found himself in Dodge City, Kans., one evening in the early '90s before he hit the big time, and the artist had Gunsmoke — the classic CBS western set in that city — on his mind.

“I think we were actually at the Long Branch Saloon or Miss Kitty’s Saloon — it was something to do with Gunsmoke,” Keith recalls. “This highway patrolman who I had met on the trip, his name was John, he jumps up. He was probably 45 or 50 back then, and he runs over to this 25-year-old cowgirl. He was going to show that he could bust a move. She turns him down. He comes over, and said, ‘She says she doesn’t dance.’ About 15 minutes later, a young cowboy comes in — and off they go on the dance floor. Everybody was making fun of him, and one of the guys said, ‘John, I guess you should have been a cowboy.' ” 

The wheels began to turn in Keith's head and "Should've Been a Cowboy" was born. “I thought, ‘I betcha never heard Marshal Dillon have any woman problems because Miss Kitty was always knocking his back door down.' I just started writing it, and it grew into Jesse James riding shotgun, and Gene and Roy. It all happened in about 20 minutes.”

"Should've Been a Cowboy" became Keith's first single for Mercury Records in the winter of 1993, and eventually topped what was then Billboard's Top Country Songs chart for two weeks in June. This Wednesday (Dec. 5), the singer celebrated the 25th anniversary of the song that broke his career wide open with a party at BMI's Nashville office. 

Looking back, he recalls the moment he knew he was on to something. He was working with producer Harold Shedd, who'd signed him to the label. "When they put that western baritone guitar on there, that’s when magic happened in the studio," Keith says. "The session guys in the studio were going, ‘This song is a big hit.’ That’s what you want for your first one. I knew the second they put that guitar part on that it was going to be a single, but after a couple days, I was getting feedback from everyone that it was going to be a big hit.”

The song kicked off a career that has seen Keith's songs appear 75 times on Billboard's country singles chart over the years — including 20 chart toppers. The majority of those songs feature his name as a songwriter, a designation in whichtakes great pride.

Songwriting, he says, has been the most important part of his career. "Even when I was playing in bar bands, during the day we'd be laying around the motel, we'd be in a town for four or five days. I'd be sitting around and writing songs all the time. I wanted to be better at it and I wanted to write the best songs I could write. So if I wouldn't have gotten a recording contract and had some success, I would have still been pitching songs. God forbid, if something ever happened to you and you couldn't sing no more or perform, you could still write songs.”

One of his most recent writing credits is for a song, “Don’t Let The Old Man In,” that appears in the new Clint Eastwood film The Mule, which opens Dec. 14. Keith admits to being a little starstruck upon meeting the box-office legend. 

“I couldn’t not quit working on it. It was one of my favorite things I've done in my life,” Keith says. “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 wanted to deliver him the best thing I could," he says. “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.”

The stark performance on “Don’t Let the Old Man In” stands in contrast to some of Keith’s radio fare over the years. Though he no longer tries to sway the gatekeepers at country radio at this point in his career, that wasn’t always the case.

“Those first four or five albums, the label said, ‘You can't cut this song because radio's not going to play it. We only want stuff that radio's going to play,' " he says. "So you're kind of at their discretion on what you get to do. And then you box out of that shell and figure out for yourself what works. Harold Shedd said it best. He said, ‘Nobody knows your audience better than the audience. I trusted that I knew it and that's when I got fearless. I went after them.”

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