In February of 1993, Toby Keith released his debut single, “Should’ve Been a Cowboy.” Co-produced by Nelson Larkin and Harold Shedd — the pair that co-produced all of Keith’s self-titled debut album — the song is about a man wistful for a different kind of life.
More precisely, the protagonist of “Should’ve Been a Cowboy” feels as if he’d fit in better elsewhere, in a place where he had a little more freedom, both emotionally and spatially: “Go west, young man; haven’t you been told? / California’s full of whiskey, women and gold,” Keith sings. “Sleeping out all night beneath the dessert stars / Dream in my eye and a prayer in my heart.”
In keeping with the song’s freewheeling, restless-cowboy theme, the lyrics of “Should’ve Been a Cowboy” reference Gunsmoke, the Texas Rangers, Jesse James and “Gene and Roy” (that would be Autry and Rogers, respectively). Musically, the song is relatively simple and streamlined — pedal steel and honky-tonk guitar dominate — which makes room for a catchy, buoyant hook and Keith’s twangy vocals.
That “Should’ve Been a Cowboy” resonated meant the world to the then-new act. In 2010, he told CMT he first heard “Should’ve Been a Cowboy” on the radio while on a bus en route to Bowling Green, Ky., with Shania Twain.
“Those are good memories,” Keith says. “We left Nashville as a bunch of greenhorns and went up into Kentucky and flipped the radio on. “Should’ve Been a Cowboy” came on, and it changed my life.”
In that same article, CMT reports that “Should’ve Been a Cowboy” was the most-played country song of the 1990s on the radio, and (at the time) had received more than 3 million spins overall. It’s no surprise, then, that the gold-selling song hit No. 1 on Billboard‘s Hot Country Songs chart (and No. 93 on the all-genre Billboard Hot 100).
“Should’ve Been a Cowboy” has earned a second life in the college football world as well: Keith, a die-hard University of Oklahoma Sooners fan, once described how he heard the tune played during an Oklahoma State University Cowboys game.
“I went up [to Stillwater, Okla.], and watched OU play OSU two or three years ago … and OSU beat the fire out of them,” Keith said in 2009. “And every time they scored, they played it. Then, at the end of the game, as we were leaving the stadium, they had it on a loop.
“I bet it played 20 times in a row, just over and over and over and over,” Keith adds, “and the irony of getting your butt kicked and walking out there and hearing your song play was pretty crazy.”
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