More Than A Cowboy: Toby Keith’s Enduring Legacy
The country music world was left in mourning in 2024 when one of its most successful — and most controversial — singer-songwriters passed away at the age of just 62. Toby Keith shot to fame in the mid-1990s with a string of cowboy anthems, but he became more renowned in the ‘00s for his outspoken views and fervent patriotism in the wake of 9/11. Whether you were a fan or not, his 20 Hot Country number ones, 40 million sales, and seven Grammy nominations are the stuff of legend.
Cancer diagnosis
Keith first revealed to the world that he had stomach cancer in the summer of 2022 having first been diagnosed in the fall of the previous year. He told his fans on X, then Twitter, “I’ve spent the last six months receiving chemo, radiation, and surgery.”
“So far, so good. I need time to breathe, recover, and relax. I am looking forward to spending this time with my family. But I will see the fans sooner than later. I can’t wait.”
Roller coaster
The “Should’ve Been a Cowboy” singer vowed to fight the disease and continued to play live as he did so. He spoke of his progress to E! News at the 2023 People’s Choice Country Awards, where he performed The Mule soundtrack number “Don’t Let the Old Man In.”
Keith said, “It’s a little bit of a roller coaster. You get good days and, you know, you’re up and down, up and down. It’s always zero to 60 and 60 to zero, but I feel good today.”
Viva Las Vegas
And then just a few months later, Keith headlined three dates in Las Vegas which instantly sold out. Announcing the dates, the star told fans, “Through COVID and cancer, the old Devil’s been at me a little bit.
I’ve got him by the horns right now. So instead of just sitting around and waiting, we’re gonna get the band together.” Sadly, this would be the last time Keith appeared on stage.
Grace and courage
Just two months after his Vegas residency, Keith died while surrounded by his loved ones. A statement released by the family said, “He fought his fight with grace and courage.”
The country icon was survived by his three kids Stelen, Krystal, and Shelley, and wife of more than four decades, Tricia. The “How Do You Like Me Now?” singer also had four grandkids, as he proudly showed in a photo published on his Instagram page during his final Christmas.
Moore farm
Keith was born in 1961 in the Oklahoma city of Clinton and enjoyed a childhood far removed from the bright lights of the showbiz world. He spent most of his early years on a farm in Moore, just outside Oklahoma City.
It was here where he developed his talents as a guitarist. Keith was particularly enamored with his father’s country music collection, which included the likes of Merle Haggard and Bob Wills.
Oil fields
You might not be aware that Keith began his career in Oklahoma working in the state’s oil fields. It was a role which made him rich beyond his wildest dreams, as he told the Associated Press in 1996.
Keith said, “The money to be made was unbelievable. I came out of high school in 1980 and they gave me this job December of 1979, $50,000 a year. I was 18 years old.”
Oklahoma City Drillers
Keith was forced to make his first career pivot with the collapse of the oil field industry. He started playing regularly for the Oklahoma City Drillers as a defensive end.
But after two seasons as a footballer, Keith decided that his talents lay elsewhere: the stage. Yes, by this point, the singer was also busy making a name for himself on the roadhouse scene across Texas and Oklahoma.
Although Keith acknowledged at the time that forging a country music career wasn’t going to be easy, he persevered. And during a trip to Nashville, he impressed Harold Shedd, the boss of Mercury Records, enough to land a record deal.
The singer-songwriter released his self-titled debut in April 1993 and thanks to breakthrough smash “Should’ve Been a Cowboy,” he instantly became one of the new darlings of the country scene.
Sticking to roots
Despite scoring the genre’s most-played hit of the decade, Mercury allegedly tried to push Keith in a different direction, with the unprecedented pop crossover success of Shania Twain reportedly the goal.
But the ex-footballer wasn’t interested in betraying his roots. He told the AP, “They were trying to get me to compromise, and I was living a miserable existence. Everybody was trying to mold me into something I was not.”
ACM Awards
Keith proved he could cross over to the mainstream in his own way at the turn of the century after signing to Dreamworks Records. “How Do You Like Me Now?!” became his first Top 40 hit on the Hot 100.
And then in 2001, Keith picked up both Album and Male Vocalist of the Year at the Academy of Country Music Awards. During his acceptance speech, the proud star said, “I’ve waited a long time for this. Nine years!”
The Angry American
Following the attacks of 9/11, Keith appeared to appoint himself as the voice of America. In 2002, he released Courtesy of the Red, White and Blue (The Angry American) in response to the tragedy.
It wasn’t exactly subtle. Lyrics included “We’ll put a boot in your… [behind] – It’s the American way.” But it struck a chord with certain audiences still trying to make sense of the situation.
Steve Earle
Not everybody appreciated its strong patriotic spirit, though. Producers of a Fourth of July special screened by ABC decided to drop the track over concerns that it expressed a little too much anger for prime-time TV.
It’s fair to say that fellow troubadour Steve Earle wasn’t exactly a fan, either. He described “The Angry American” as “pandering to people’s worst instincts at a time they are hurt and scared.”
Dixie Chicks
A year on, Keith made an enemy of another country-music favorite. This time it was the band then known as the Dixie Chicks. The all-female trio had already suffered a major backlash from conservative fans, you may remember.
This started when Natalie Maines told a London crowd that the band were ashamed to hail from the country that had George W. Bush as its president. Keith certainly didn’t concur.
Freedom of speech
Despite previously advocating for freedom of speech, Keith blasted Maines for her comments. And he made his feelings on the matter even clearer when he showed off a Photoshopped image of the Dixie Chicks star alongside Saddam Hussein.
In response, Maine took to the ACM Awards of 2003 sporting a T-shirt with the acronym FUTK. We’re far too polite to spell out what these letters stood for, but you can probably guess.
Entertainer of the Year
This war of words didn’t exactly do Keith’s career any harm, though. At that very same ceremony, he was crowned Entertainer of the Year. The star wasn’t there to pick up the award.
He’d stormed out earlier in the evening, aggrieved on losing in various other categories. The ACM panel didn’t hold a grudge, though: they awarded him the exact same award the following year, too.
Military man
Keith proved he wasn’t all talk when it came to his love of the U.S. military. He regularly performed in front of troops, embarking on no fewer than 18 United Service Organizations tours.
His philanthropic endeavors didn’t end there, either. He was responsible for raising seven-figure sums throughout his career, and even helped build a home for children suffering from cancer in his native Oklahoma.
Creative control
In 2005 Keith took more creative control of his career than ever before when he and Scott Borchetta, a record executive who also founded the Big Machine label, launched their own Show Dog label.
The “You Shouldn’t Kiss Me Like This” singer was fully aware that not everyone was in his corner. He said, “Probably 75 percent of the people in this town think I’ll fail, and the other 25 percent hope I fail.”
Show Dog
But Show Dog proved to be a big success thanks to signings such as Joe Nichols, Clay Walker, and Trace Adkins. Keith himself continued to have hits, too, including “Red Solo Cup” and “She Never Cried in Front of Me.”
And in 2015 he received the honor of an induction into the Songwriters Hall of Fame. Keith later said, “I always felt like that the songwriting was the most important part of this whole industry.”
100% Songwriter
Keith further emphasized his love of penning original material with a 2023 compilation aptly titled 100% Songwriter. This gathered 13 compositions the country star had written without any outside assistance.
Sadly, this turned out to be the final Keith album to hit the shelves in his lifetime. But his music will undoubtedly continue to live on: just watch the 2024 CMT Awards tribute for proof.
CMT Awards
Yes, taking place just a month after Keith’s untimely death, the Country Music Television Awards was understandably keen to pay respect to one of its regular faces. And the organization roped in several other iconic names to help.
Alongside Keith’s regular backing group and mentee Lainey Wilson, longtime pals Sammy Hagar and Brooks & Dunn took to the stage to honor the star. And there wasn’t a dry eye in the house afterward.
Humor and wit
The star-studded performance was introduced by the baseball icon Roger Clemens, who described Keith as “a true friend and patriot.” The former Boston Red Sox pitcher also discussed how his pal had coped during his battle with cancer.
Yes, Clemens noted how the “A Little Less Talk and a Lot More Action” singer had always “kept his sense of humor and his wit.” And then he offered a perfect example as proof.
The Eyes of Texas
Clemens told the audience, “My two boys, who played baseball right here at the University of Texas, they were in Oklahoma playing the Sooners at [University of Oklahoma], Toby's university.”
“Toby told my boys, ‘If you get a home run off our Oklahoma pitcher today, I’ll sit on your dugout and I’ll sing the “The Eyes of Texas” with you.’”
Working on the railroad
“Well, guess what?,” Clemens went on to add. “It happened and, true to form, Toby sat on the dugout and with his funny and wit, sang, ‘I’ve been working on the railroad.’”
“No chance was he going to sing ‘The Eyes of Texas.’" Sadly, neither of these ditties were performed in the musical tribute, but all the same, no one in the CMT Awards crowd was complaining.
Brooks & Dunn
First up were country duo Brooks & Dunn, who chose to throw things back right to the beginning with a cover version of Keith’s 1993 first hit, “Should’ve Been a Cowboy.”
Their rendition instantly set the mood, inspiring everyone in the crowd, including singer Jelly Roll, to sing along in unison. And then it was the turn of the man known as the Red Rocker.
Sammy Hagar
Hagar kept up the energy of Brooks & Dunn with a rousing performance of “I Love This Bar,” the beloved 2003 track which inspired the name of Keith’s restaurant franchise.
The frontman of metal legends Van Halen joked that while it should be impossible to get thrown out of your own establishment, both he and Keith had managed it several times during the course of their friendship.
Forever a Sooner
Hagar explained, “We had this routine. I’d go down early and I’d be on stage with the band and I’d see this big commotion going on at the front door.”
“And I would look up and big dog daddy and his posse walking through the door and I would turn to the band and I would say…” The rocker then launched into Keith song “I Love This Bar” before unveiling a shirt which read “Forever a Sooner.” By the way, in case you’re mystified, a “Sooner” is a term for a settler who entered the Unassigned Lands in what is now the state of Oklahoma.
Lukas Nelson
Then two other admirers took to the stage. Firstly, Lukas Nelson, the son of country icon Willie, shared a story about when he had been first introduced to Keith. He told the crowd, “Toby was not a shy guy.”
“He had a big personality. I met him when I was younger when he was working on ‘Beer for My Horses’ with [my dad]. I got lucky I got the opportunity to watch his artistry in person.”
Riley Green
Riley Green then paid his own personal tribute to Keith. The “There Was This Girl” hitmaker said, “That guy could come up with a hook like no other and sing the Hell out of every song that he wrote.”
Green added that he was always impressed at how Keith had been able to make the whole process look so easy. He then wrapped up, “Right now, we have one of our favorite artists to perform one of our favorite Toby songs.”
Lainey Wilson
After Nelson and Green left the stage, Grammy Award winner Wilson brought the tribute to a close with a powerful take on the title track to 1999’s How Do You Like Me Now?
This was the performance that appeared to move Keith’s widow the most. Yes, Tricia Lucas was also in attendance at the annual ceremony with their children Stelen, Krystal, and Shelley.
No-brainer
Wilson had told Fox News earlier on in the night that performing at the ceremony was a no-brainer. She said, “I don't know anybody in this business that doesn't love Toby.”
“He was truly the soundtrack to my childhood.” The “Things A Man Oughta Know” hitmaker then explained to the network exactly how Keith had made an impact on her career.
Going against the grain
Wilson told the reporter, “Seeing all of his stuff and all the visions that he had come to life, it made me feel like there’s nothing wrong with being fearless.”
“There’s nothing wrong with going against the grain and standing up for what you believe in and being unapologetically yourself.” And the rapturous response to Wilson’s performance proved that she’d learned Keith’s lesson well.
Following Wilson’s emotive rendition of “How Do You Like Me Now?” Clemens returned to the stage to raise another toast to Keith. He told the late country star’s children, “Thank you for sharing your dad with all of us. Thank you.”
Clemens, who has won the World Series on two occasions, then addressed Keith’s wife with the heartfelt words, “Trish, we love you. Thank you for sharing your husband with the world, Trish. Thank you.”
Clemens then finished his poignant crowd-pleasing speech by referencing two of Keith’s best-loved and most enduring country songs. The Major League Baseball icon said, “Alright, real quick. Raise ‘em up.”
“Everybody at home, raise your fist if you don't have a Solo cup. Let Toby hear you. Repeat after me, ‘Whiskey for my men,’ and, ‘Beer for my horses.’ Let’s go.”
“Honor to be asked”
Before the ceremony began, Clemens told Us Weekly while walking the red carpet that he had been grateful for the opportunity to pay his respects to Keith in such a public way.
He said, “Hopefully, I don’t get too emotional. We miss him dearly and just an honor to be asked to come and present one of his songs, so I’m looking forward to it.”
“Give it my best”
Clemens went on to add, “Toby did leave us with some great songs. I mean, you know what I’m saying? A lot of great ones, and they’re fun to sing too.”
“Sometimes I can sing ’em pretty good and there’s other ones I can’t sing very well, but I give it my best.” Luckily, the baseball legend left the singing to the professionals on the night.
Tributes on social media
It’s fair to say that the star-studded CMT Awards memoriam went down well with viewers at home. One tweeted, “As a lifelong Toby Keith fan, that tribute was absolutely beautiful.”
“Seeing his babies made it even more special. Thank you for sharing him with us Shelley, Krystal, and Stelen. We miss you Toby.” Another remarked, “That Toby tribute... those red solo cups had me in shambles.”
Special occasion
The CMT Awards had always been a particularly special occasion for Keith. The star picked up no fewer than 30 nods at the ceremony over the years, winning seven times.
He was also a regular performer, taking to its stage on 13 occasions. And Keith even hosted the ceremony twice, firstly in 2003 alongside Pamela Anderson and then nine years later with Kristen Bell.
CMT special
With that in mind, the CMT network also paid further tribute to the late country star with a special aired after its 23rd annual ceremony, CMT Music Awards Celebrate Toby Keith.
The show compiled many of the star’s finest moments on one of the country music world’s biggest nights. The hour-long program also featured appearances from many of the artists who’d just honored his career on stage.
Final recording
And Keith’s output is continuing to resonate with fans. His final studio recording, a cover version of Joe Diffie’s “Ships That Don’t Come In” which also featured Luke Combs, was released on Hardy’s Hixtape album a month after his death.
And Keith’s most recent retrospective is still selling in its thousands as it takes up residency on the Billboard 200. Expect Keith’s music to still be part of the country landscape for many more years to come.