Some Parting Thoughts on Toby Keith

Toby Keith as he appeared at his debut,
with that signature icky 1990s mullet

When Toby Keith’s debut single, “Should’ve Been a Cowboy,” raced to #1 on the Billboard country charts in 1993, I still listened to country radio. I hadn’t grown jaded on the peppy country-pop hybrid that would overtake mainstream country music in the 1990s, an overtaking that Keith helped facilitate. Therefore, I heard it go into regular rotation, as country disc jockeys praised Keith’s tapping into the key country music zeitgeist.

“Should’ve Been a Cowboy” dropped when Keith was 31 years old. That’s older than most aspiring musicians get before they quit, disgusted with dead-end opportunities and industry gatekeepers. It’s also remarkably old to debut in country music. Despite its middle-aged conservatism, since the 1990s, country music has notably disdained artists past forty. America teems with musicians every bit as competent and inventive as Johnny Cash who quit because they needed groceries.

Despite being only nineteen myself, I recognized the sentiment dominating “Should’ve Been a Cowboy.” Keith’s surface-level themes aren’t exactly concealed: his life lacks spark that would’ve been present had he lived in another time and place. I appreciated the sentiment as, in 1993, I struggled with meaningless jobs while living in a Western Nebraska town that celebrated its cattle drive-era heyday. It’s impossible to ignore the past’s alluring appeal.

However, I also recognized something below Keith’s surface-level themes. Despite longing to be a “cowboy,” his song never mentions the workaday tedium of cowpunching. Instead, he cites Gunsmoke, The Lone Ranger, and the classic “Singing Cowboys,” Gene Autry and Roy Rogers. He wants to romance women, chase outlaws, and sing around the campfire. He presents a cowboy mythology completely devoid of actual cattle work.

In 1993, I lacked the vocabulary to explain something that I innately understood, but would only verbalize years later: the legendary Wild West didn’t exist. American culture celebrated cowboys only after they were dead, inventing fine-sounding fables about heroism, hard work, and gun-barrel justice. Owen Wister’s The Virginian, the novel which defined the Western genre, begins with a prelude lamenting that cowboys, like chivalric knights, now remain only in memory.

So in extolling cowboy goodness, Toby Keith yearned to time-travel to a time that existed only in paperback novels and Hollywood fantasies. He wanted a life with the dreary bits removed, with moral ambiguity excised, with heroes and villains clearly demarcated by the color of their Stetson hats. I don’t say this unsympathetically: Keith, a former oil derrick worker, understood intimately how modern labor strips life of meaning.

Toby Keith as he appeared in 2023, thinned
by the cancer that eventually killed him

Yet the yearning for moral clarity and escapism in “Should’ve Been a Cowboy,” eventually overtook Keith’s work. Through the 1990s, Keith released middle-of-the-road Nashville fare like “How Do You Like Me Now?” and “I Wanna Talk About Me,” songs that were okay and did well on the charts. But he struggled to find his unique voice. This matters especially since, unlike other controversial Nashville artists, Keith wrote his own material.

He finally found his metier after September 11, 2001. That’s when he released the songs likely to define his legacy: “Courtesy of the Red, White, and Blue (The Angry American)” and “Beer For My Horses.” The former, known colloquially as “the Boot in the Ass song,” became an anthem of pro-war Americans during Bush’s War on Terror. The latter is a cartoonish pro-lynching song extolling cowboy myths of civilian justice.

That’s when the cosplay cowboy ethos behind Keith’s breakout single finally consumed him. No longer satisfied yearning for a past that never existed, Keith dropped himself narratively into America’s moral conflicts. Backed by Nashville’s multi-million-dollar publicity machine, he pretended to be a sandbox soldier and civilian justice-bringer. He traveled the lucrative arena circuit whipping audiences to think likewise.

Keith’s musical persona embraced absolutes. He favored “this country that I love” and inveighed “against evil forces.” He never explained exactly how he identified evil forces, except that they didn’t love America like him. In Keith’s world, apparently, evil is as evil does. Morality equated to conformity, pro-Americanism, and buying into the official state narrative. His cosplay righteousness wasn’t in the past anymore, it was merely silenced in the present.

But the shine eventually wore off the War on Terror. As America abandoned absolutism and relearned that difficult situations deserved more nuanced treatment, Keith stopped making hits. His songs remain popular with the flag-waving crowd, but he last creased country’s Billboard top twenty in 2012. His final years were characterized by silliness like “Red Solo Cup.” Country music moved on, leaving his absolutism behind. So, I hope, did the country.