Toby Keith, Complicated Conservative

Estimated read time 6 min read

Toby Keith, Complicated Conservative

Keith’s unembarrassed patriotism made him a provocative throwback.

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Credit: Getty Images/ Credit: Rick Diamond

Country music lost an icon this week. Toby Keith passed away Monday after a battle with stomach cancer. He was 62. 

The Oklahoma native was a larger-than-life entertainer with a penchant for patriotic anthems that his critics would label jingoistic. The man known as “Big Dog Daddy” was far more nuanced than his over-the-top persona and hit songs would suggest. Keith, born Toby Keith Covel, lived a quintessentially American life. It engendered in him a true love for this country, one marked by a sincerity that is increasingly scarce and scorned.

Before his post-9/11 anthems made him into a cultural flash point, the self-described “oil field trash” and former semi-pro football player was a key figure in the neotraditionalist revival of 1990s Nashville. Keith’s debut single, 1993’s “Should’ve Been a Cowboy,” was a runaway hit, reaching number one on the charts and becoming the most-played song of the decade. The song is filled with references to Western culture that would have been widely familiar to a previous generation of Americans: Marshal Matt Dillon and Miss Kitty of “Gunsmoke”; singing cowboys Gene Autry and Roy Rogers.  

“Should’ve Been a Cowboy” was also a notable hit in that it was written by Keith himself. Unlike many of his contemporaries, Keith established himself as both an accomplished performer and songwriter, penning the majority of his hits. While his discography includes its fair share of shallow party songs (“Get Drunk and Be Somebody,” or “Red Solo Cup”), he was firmly rooted in country music’s storytelling tradition of “three chords and the truth.” His 1995 hit “Who’s That Man,” for example, is a poignant narrative of a tormented divorcé watching another man move in and live his former life with his wife and kids. (Keith, for his part, wasn’t singing from personal experience. He was married to his wife, Tricia, for nearly 40 years.)

Until 2001, Keith seemed destined to continue as a consistent hitmaker within country music’s cultural confines. But after the terrorist attacks of September 11, Keith transcended Nashville. While Alan Jackson’s “Where Were You (When the World Stopped Turning)” captured the fear, confusion, and sadness the country was feeling after 9/11, Keith’s “Courtesy of the Red, White, and Blue” captured the anger. He wrote the song in 20 minutes on the back of a Fantasy Football sheet. It took off like wildfire, hitting number 1 on the country chart, and giving voice to a simmering desire for retribution:

Justice will be served and the battle will rage

This big dog will fight when you rattle his cage

And you’ll be sorry that you messed with

The U.S. of A.

‘Cause we’ll put a boot in your ass

It’s the American way

Keith was transformed into a reluctant culture warrior. He became the foil to the Dixie Chicks, who were increasingly critical of the Bush administration—and of Keith. Natalie Maines, the group’s lead singer, famously called “Courtesy” “ignorant.” Maines later stepped up the feud by wearing a t-shirt emblazoned with “FUTK” to the 2003 ACM Awards, a not-so-subtle jab at Toby Keith’s initials.

With war hawks straining to read “in Iraq” into Keith’s lyric, “A mighty sucker punch came flying in from somewhere in the back,” it’s undeniable that “Courtesy” fueled the war drums of the time. The song’s conflation of righteous anger with an undiscerning desire for revenge (Alan Jackson spoke for many Americans when he sang, “I’m not sure I can tell you the difference in Iraq and Iran”) certainly played a role in boosting public support for the invasion of Iraq. Yet Keith’s own opposition to the Iraq war—he famously said he “never did” support it in a 2007 interview—shows that the singer was more complicated than a mere GOP partisan.

“Courtesy of the Red, White, and Blue” was also written in the wake of the death of Keith’s father in March 2001. Hubert Keith Covel was an Army veteran—and a lifelong Democrat. His son maintained an independent streak politically, first as a self-described “conservative Democrat,” then as a registered Independent who would at times praise both Barack Obama and Donald Trump. 

Keith’s more recent work is instructive to understanding both his own politics and the political trends happening in the country he loved. Between the scores of booze-fueled anthems, a populist and fiercely patriotic message emerges. There’s an affinity for marijuana (“Weed With Willie,” “Wacky Tobaccy,”) along with a tough-on-crime ode to capital punishment (“Beer for My Horses”). 2009’s “American Ride” sounds traditionally conservative notes on illegal immigration and religion in the public square, while 2011’s “Made in America” could double as a blue collar, pro-union case for protective tariffs.

After Donald Trump’s shock election in 2016, the 45th president’s inaugural committee had the unenviable task of organizing an inaugural celebration. The scores of A-listers who had headlined Barack Obama’s “We Are One” celebration eight years earlier weren’t lining up to celebrate the Bad Orange Man. Instead, the “Make America Great Again Welcome Celebration concert” featured rock group 3 Doors Down and country acts Lee Greenwood, The Frontmen of Country (pulling from ‘90s groups Lonestar, Restless Hearts and Little Texas), and—the biggest star of the event—Toby Keith. 

Keith, already pigeonholed as a red state icon, undoubtedly knew that his presence would be taken as further support for Donald Trump. He didn’t care. He put politics aside for the evening, and avoided overt political messaging on stage. Between “American Soldier” and “Made in America,” performed against the backdrop of a flag-draped screen at the Lincoln Memorial, Keith offered his only message of the evening: one of gratitude for service to the country he loved.

“On behalf of my family, my band, and all my fans, I want to salute the Army, Navy, Air Force, Marines, and Coast Guard,” he said, “Thanks to Barack Obama for your service, and thanks for the 45th President of the United States, Donald Trump. I salute you.”

In 2024, such sincerity is easily doubted and mocked. But amidst the countless USO tours and benefit concerts, perhaps Keith’s greatest service to this country is that he reminds us of a time when that wasn’t so. Toby Keith—the man who wrote of the Angry American, the Drunk American, the American soldier, the American ride—sincerely and unapologetically loved this country. May his songs remind us that we should, too.

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