On June 5, 1993, Toby Keith earned his first No. 1 song on the Hot Country Songs Billboard chart, "Should've Been a Cowboy." Keith wrote the song himself; it was his debut single.

Co-produced by Nelson Larkin and Harold Shedd -- the pair that also co-produced all of Keith's self-titled 1993 debut album – "Should've Been a Cowboy" features lyrics that are based on a true story: Keith wrote the tune in a hotel bathroom, after a bar experience where a woman chose a cowboy over one of his friends. Accordingly, "Should've Been a Cowboy" is about a man wistful for a different kind of life; in fact, the protagonist 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.

In the end, "Should've Been a Cowboy" didn't just hit No. 1 on the charts: It also ended up being the most-played country song of the 1990s on the radio, having received well over 3 million spins overall as of 2010. Keith has gone on to earn 19 more No. 1 songs, making him one of the most successful modern country artists; as such, he was inducted into the Songwriters Hall of Fame in 2015.

Keith commemorated the success of his debut single throughout 2018 with the Should've Been a Cowboy Tour XXV; naturally, he played the titular song on the trek. "Should've Been a Cowboy" has also earned a second life in the college football world: 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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