Witnessing a man rejected by a woman right on the dancefloor, inspired Toby Keith to write his first hit “Should’ve Been a Cowboy.” At the time it was written, Keith was on a pheasant hunting trip with friends in Dodge City, Kansas, and had the 1950s to mid-’70s Western TV series Gunsmoke on his mind.
“The town had a few things in there that played off that [the show],” said Keith. “And I think we were actually at a place called the Long Branch or Miss Kitty’s Saloon—something to do with ‘Gunsmoke.’ It was a steakhouse and combo, five o’clock kind of thing. We’re all in hunting clothes, there’s 20 guys, and they’re feeding us.”
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A Dancefloor Diss
Keith went on to explain the scene that played out and inspired “Should’ve Been a Cowboy,” which was written later that night. “This highway patrolman who I’d met on this trip, his name was John, he jumps up, and he was probably 45 or 50 back then,” said Keith. “And he runs over by a 25-year-old cowgirl, and he says he was gonna show how he can bust a move. She turns him down, and then a few minutes later, he comes back and says ‘She don’t dance,’ So they’re giving him a bunch of steam over it.”
Around 15 minutes later, Keith said a younger cowboy walked in, and off cowgirl went on the dancefloor with him. “Everybody’s making fun of him [patrolman], and somebody says, ‘John, I guess you should’ve been a cowboy,” remembered Keith. “I thought I oughta write ‘Should’ve Been a Cowboy.’ I didn’t know what to do with it. So I thought, ‘I betcha never heard Marshall Dillon say he had any woman problems, ’cause Miss Kitty was always knocking his back door down.’”
He added, “I started writing it, and it grew into Jesse James and riding shotgun and Gene [Autry] and Roy [Rogers]. It all happened in about 20 minutes.”
After heading back to his hotel room, Keith wrote what would become his first single and first No. 1 hit. Released on Feb. 12, 1993, on Keith’s eponymous 1993 debut, “Should’ve Been a Cowboy” topped the Billboard Hot Country Songs chart and also went to No. 1 in Canada.
[RELATED: 3 Songs You Didn’t Know Toby Keith Wrote for Other Artists]
Western Woes
Throughout the song, Keith is writing from the perspective of a man who regrets not learning the ways of a cowboy, of singing campfire songs, learning to rope and ride, going after outlaw Jesse James, and sweeping women off their feet like Roy Rodgers and Gene Autry.
I bet you’ve never heard ol’ Marshal Dillon say
Miss Kitty, have you ever thought of runnin’ away?
Settlin’ down, would you marry me
If I asked you twice and begged you, pretty please?
She’d have said, “Yes”, in a New York minute
They never tied the knot, his heart wasn’t in it
He just stole a kiss as he rode away
He never hung his hat up at Kitty’s place
I should’ve been a cowboy
I should’ve learned to rope and ride
Wearin’ my six-shooter, ridin’ my pony on a cattle drive
Stealin’ the young girls’ hearts
Just like Gene and Roy
Singin’ those campfire songs
Woah, I should’ve been a cowboy
I might of had a sidekick with a funny name
Runnin’ wild through the hills chasin’ Jesse James
Ending up on the brink of danger
Ridin’ shotgun for the Texas Rangers
Go west young man, haven’t you been told?
California’s full of whiskey, women and gold
Sleepin’ out all night beneath the desert stars
With a dream in my eye and a prayer in my heart
“Should’ve Been a Cowboy” was one of the most-played country songs in the ’90s. Along with Keith’s other 31 chart-toppers, “Should’ve Been a Cowboy” was the first to help the country star get inducted into the Songwriters Hall of Fame in 2015.
Along with his other hits like “Red Solo Cup,” “I Love This Bar,” “A Little Too Late,” “As Good As I Once Was,” “How Do You Like Me Now?,” “Beer for My Horses,” “Who’s Your Daddy?,” and more, Keith always had “Should’ve Been a Cowboy” on his live setlists through his final concert on December 14, 2023, nearly two months before his death on February 5, 20224 at 62.
Kentucky Radio
The song was pivotal and a special one for Keith, who always remembered the first time he ever heard it on the radio. While traveling from Nashville, Tennessee to another show in Louisville, Kentucky, when the band arrived in the city of Bowling Green, they heard the song come on.
“Everyone just shut up and when it came on, we cranked it up,” remembered Keith during the 25th anniversary of the song and his debut album in 2018. “It’s such an important piece of the puzzle that I don’t think I’ve ever done or will ever do a show without playing it.”
Photo: Matt Winkelmeyer/Getty Images for iHeartMedia
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