The Stunning Impact & Surprising Complexity of Toby Keith

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Toby Keith was a country music star, and one of the most important and successful to ever do it. In the first decade of the 2000’s, there was no country music artist that was more commercially successful than Toby Keith, both as an entertainer, and as a businessman. Keith put 20 #1 singles on the charts during an eight year run, and had another seven #2’s during this same period. Toby Keith was mainstream country music in the aughts.

Toby Keith was an American, and perhaps one of the most outspoken, supportive, and high profile champions of the American ideal and those who were sworn to protect it in flesh and blood than anyone else in public life. Like so many Americans enraged about the sucker punch of September 11th, 2001, Keith put those emotions into song in ways that embodied the very emotions people felt, and in paramount and unprecedented ways, pushing the envelope of acceptable parlance.

But most importantly, Toby Keith was a human. This was brought into stark contrast recently after years of slowly fading away from the country spotlight like so often happens with aging country stars, while also slowly deteriorating due to the ravages of stomach Cancer. The illness took a man who was once a tower of a person to just a frail, hollowed-out version of his previous boisterous self, putting Toby Keith’s humanness on full display for both his supporters and detractors to see in ways that drew sincere concern and empathy across cultural and political divides.

Now Toby Keith is gone, and all that is left is a range of emotions that for many might be as strong as the ones people may feel for a close friend or family member, while for others they will be as complex as the man’s legacy itself. But like Toby Keith did throughout his career, his death will make you feel something, and strongly. Because that’s what Toby Keith did. He took the emotions we all feel in the deepest moments of passion, and brought them to the surface.

“Should’ve Been a Cowboy” was the first single from the Oklahoma native in 1993, and it was a massive one. Now a country music standard that’s Certified Triple Platinum, it announced what would be a career that will eventually land in the Country Music Hall of Fame, and it did with with a traditional country song that helped define the ’90s country era.

More hits would come in the next eight years for Mercury Nashville, but the fact that the label put out a Greatest Hits compilation on Keith in 1998 tells you a lot. At that time, they thought Toby Keith was done. As we would see in the coming years, he was just beginning.

2002’s “Courtesy of the Red, White and Blue (The Angry American)” written in direct response to 9/11 is what would go on to define the career of Toby Keith, as well as popular country music for the next decade. The stark language in the song drew its opponents, but that polarization only lent to the song’s popularity. “Beer For My Horses” with Willie Nelson in 2003 not only put a country legend back on the charts, it continued the type of sabre rattling songs that would become Toby Keith’s signature.

2003 saw Toby Keith’s album Shock’n Y’all, whose title exploited the fact that Toby Keith’s stark Americanism drew the ire of many. But unabated, Keith redirected the criticism into a point of pride.

Though Keith would be considered the seat of American jingoism for many in the post 9/11 world, his actual political legacy was significantly more nuanced. At the time “Courtesy of the Red, White and Blue (The Angry American)” was released, Toby Keith was a registered Democrat. Though Keith will be criticized for performing for Donald Trump, he also performed for multiple Democrat Presidents as well.

Above political party or personal beliefs, Toby Keith was an American, and one whose support for American troops was well beyond pro forma, with his USO commitments and charity work verifying Keith’s sincerity as country music became a bastion for sometimes symbolic and even exploitative “support the troops” sentiments in Toby Keith’s wake.

Many remembrances will list Toby Keith’s accomplishments. But two things are in danger of being overlooked in their proper context.

First, Toby Keith was a songwriter. Dissimilar to many country music stars of the present—and on a unprecedented scale in the modern context—Toby Keith wrote most all of his own songs, including, if not especially his hits. Brushing aside Toby Keith the performer, Toby Keith the songwriter is one of the most successful of the era, and one of the most successful to ever do it in country music.

Speaking of success, another significant element of Toby Keith’s career was his role as a label owner and entrepreneur.

When Big Machine Records CEO Scott Borchetta was forming the label in 2005, Toby Keith, who at the time had a license to print money from all his chart success, wisely invested in a label that was initially supposed to be a joint partnership with Borchetta. However the partnership didn’t last long, and by 2006 Borchetta had spun off what became Big Machine, and Toby Keith became the owner of a label called Show Dog. Show Dog merged with Universal South in 2009, and became known as Show Dog-Universal.

Through his ownership of both Show Dog-Universal and his minority stake in Big Machine, Toby Keith regularly appeared or topped the Forbes list of highest paid country entertainers for a given year, even well after his chart success started to subside.

The fading of Toby Keith’s popular music career happened rather quickly once it commenced, perhaps fueled in part by the polarizing nature of his music and persona, which the country music industry was ready to distance from after the cancellation of The [Dixie] Chicks, who were one of Keith’s biggest opponents. Toby Keith would become a favorite whipping boy of certain politically-motivated characters, including Dixie Chicks front woman Natalie Maines, who wore a shirt emblazoned with “F.U.T.K” at the 2003 ACM Awards.

Actor Ethan Hawke once penned an embellished story for Rolling Stone about a confrontation between Keith and Kris Kristofferson that both men denied, with Keith supposedly saying to Kristofferson, “None of that lefty shit out there tonight, Kris.” Keith didn’t do himself any favors by trying to hold onto his radio relevancy and releasing his final major song, the Triple Platinum and silly “Red Solo Cup” that even Keith admitted later on was a stupid song.

But before Toby Keith would ride off in the sunset “Just like Gene and Roy,” he’d have a resurgence, and reconciliation with a lot of listeners.

Two days before Clint Eastwood was to start filming on his movie The Mule—which incidentally was two days before his 88th birthday—Eastwood was golfing with Toby Keith in a charity golf tournament at Pebble Beach. Keith marveled that the elder Eastwood was still able to get about, let alone work. Eastwood said to Keith, “I just get up every morning and go out. And I don’t let the old man in.” Toby Keith knew immediately he had to write a song with that line.

The song ended up being used in Eastwood’s 2018 movie, but went mostly ignored by the country industry at large. But on an otherwise mediocre People’s Choice Country Awards in September of 2023, the then 62-year-old Toby Keith performed the song in the midst of his effort to come back from stomach Cancer and being honored during the presentation. He floored the crowd both in attendance and watching on television, and “Don’t Let The Old Man In” went viral, giving Keith one last hurrah in his legendary career.

Toby Keith lived a complex life that saw both adulation on a scale rarely if ever seen for a country star, along with villainization that in the passing of a person always seems petty and silly, at least to those with a conscience.

Toby Keith will go down as a towering figure in the realm of country music, American culture, and life in the post 9/11 world. How people feel about that legacy will be as complex and diverse as the man and his legacy itself.

But what will be inarguable is the incredible, crater-like impact Toby Keith had in ways that unalterably influenced culture, and that will continue to resonate past his lifetime, and likely, the lifetimes of us all.

© 2025 Saving Country Music

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