The Untold Truth Of Toby Keith

In June 2022, country music star Toby Keith announced via his Instagram that he was battling stomach cancer, and had been for six months. Keith remained active after his diagnosis, appearing at his induction into the Nashville Songwriters Hall of Fame, performing at the Daytona International Speedway, and enjoying three sold-out shows in Las Vegas in December 2023. Sadly on February 5, 2024, Keith passed away from the disease. He was 62.

It was a rare and reluctant slowdown for the Oklahoma native. Born Toby Keith Covel in 1961 (per AllMusic), Keith broke onto the country music scene in 1993 with the hit single "Should've Been a Cowboy" and hasn't left since. Mainstream recognition — and controversy — came in the 2000s with "Courtesy of the Red, White and Blue (The Angry American)" and Keith's unapologetic perspective on post-9/11 America. By his own admission (via AXS TV), Keith spent most of these years laser-focused on his work, never sure that his success would hold without constant dedication, and it was only after 20 years, numerous hits, and a sprawling number of business ventures outside of music that he began to slow down and enjoy the fruits of his labor. And he's still maintained a steady workload, with regular tours and album releases, at least until his medically necessary slowdown.

All that hard work over that span of time has led Keith to some interesting places in his life and career. Here are a few you may not have heard about.

He took a liking to music in his grandmother's club

Toby Keith was born in the small town of Clinton, Oklahoma, but he spent most of his childhood on a farm outside Oklahoma City (per AllMusic). In between homes in the Sooner State, his family spent time in Fort Smith, Arkansas, where Keith's grandmother lived. She also owned Billy Garner's Supper Club. "They don't even really have 'em anymore," Keith told the Oklahoman of his grandmother's type of establishment. "It was a tavern up front, and it only served beer. And you could pay cover from 6 o'clock on that night and go on into the back, and they had fine dining and a band and a dance floor." Grandma picked up the nickname Clancy, and her place became known as Clancy's Tavern.

After Keith and his family returned to Oklahoma, they made regular visits back to his grandma's place in Arkansas, visits the young Keith always looked forward to, according to the Herald (via Rob Adams). He spent a summer helping out at Clancy's when he was 12, and watching bands play for the nightclub was what first made him want to become a musician. Keith would draw on his memories of Clancy's for his 2005 single "Honkytonk U," and he named his 15th album after the tavern. But the chance never came to take the stage at the place that first inspired Keith; his grandmother sold Clancy's only a few years after the summer Keith spent working there.

Toby Keith, oil man

Despite his youthful enthusiasm for music, it wasn't the career path Toby Keith initially planned on. According to an interview Keith gave to Dan Rather (via AXS TV), his father and grandfather shared two vocations: military service and work in the oil fields of Oklahoma, and while the absence of a draft meant Keith had no compulsion to follow in their footsteps in the former career, he did take an interest in the latter. His original plans for after high school were to go to college for petroleum engineering (per Forbes). He ended up going out into the fields as a derrick hand straight out of high school when the price of oil shot up at the end of the 1970s. Keith's musical itch was scratched in those days by the Easy Money Band he played in with friends, though a page from his day job could take him out of commission even midway through a set (per 2 News Oklahoma).

Keith graduated from derrick hand to operation manager, and he looked back on his time in the fields as a positive experience in developing a strong work ethic. But after the oil industry experienced a bust in the early '80s, Keith's father opted to retire from the business. Keith felt lost on his own, and he was soon unemployed. Work as a bricklayer and a semi-pro football player kept him going, but Keith ultimately decided to pursue his ambitions in music.

His first hit song came out of a friend's embarrassment

Toby Keith's first album, named for himself, hit the stands in 1993, and it brought him immediate recognition. His first single off the album, "Should've Been a Cowboy," reached No. 1 on the country song charts according to The Boot. One wonders if Keith's success with the number took the sting out of the real life incident that inspired it.

As Keith remembered it for The Boot, he and a group of 20 were coming back from a pheasant hunt when they stopped at a steakhouse in Dodge City, Kansas. The restaurant, and the hunt, put the TV show "Gunsmoke" into Keith's mind. Then the highway patrolman he'd met on the trip — Keith calls him "John" — approached a young woman in cowboy clothes about a dance. She turned him down, but in less than 15 minutes, she took to the floor with a young man with a similar taste in wardrobe. The patrolman took a ribbing from Keith's group over the rejection. At one point, someone in the group — who were all clad in hunting gear — remarked, "John, you should've been a cowboy."

The line stuck in Keith's mind, alongside the memories of "Gunsmoke" the trip had brought out. "I betcha never heard Marshal Dillon say he had any woman problems," he remembered thinking. From that starting point came images of Western legends and film stars to flesh out the resulting song.

He bought his way out of a contract

According to Forbes, Toby Keith's way into the country music scene was through a stewardess who passed his demo tape on to Harold Shedd, head of Mercury Records in the early 1990s. Shedd and Keith struck a $20,000 record deal, and they later left together when Shedd opened the Nashville division of Polydor. But corporate mergers eventually saw Keith back under Mercury and Shedd's successor, Luke Lewis. The new chief did not have the same passion for Keith's music as the old one. When Keith delivered a rough cut of his album "How Do You Like Me Now?" in 1999, he was told that there wasn't a single hit among its tracks.

Lewis' antagonism toward his work didn't deter Keith. He decided that he'd rather walk and take his album with him. For $93,000, he got the rights back for "How Do You Like Me Now?" and quickly took it over to the then-fledgling DreamWorks Records. They remained his label until 2004, when DreamWorks' acquisition by Universal's Interscope was followed by a merger with Mercury. This would put Keith back under Lewis, an arrangement so off-putting that he was prepared to retire over it.

Instead, Keith burnt through the remainder of his contract, then set up shop for himself with Show Dog. "People asked me, 'what makes you think you can run a label?'" he told Reuters in 2011. But Keith was confident he had learned the ropes sufficiently to manage.

One of his hits only took 20 minutes

If "Should've Been a Cowboy" brought Toby Keith to the attention of country music fans, "Courtesy of the Red, White and Blue (The Angry American)" made his name known to the public at large, according to AllMusic. Released in 2002, the unapologetically angry response to 9/11 drew a divisive reaction from listeners. While some embraced its patriotism, others considered the song reactionary and jingoist. The controversy was enough to cost Keith a spot on the guest list for ABC's Fourth of July celebrations.

Speaking at a media event (courtesy of The Boot), Keith admitted that "Courtesy of the Red, White and Blue" came from a place of anger. While working out, he became so offended by news coverage on the proper way to respond to 9/11 that he wrote out the lyrics on the back of a Fantasy Football sheet within 20 minutes. He first performed the number for a group of Marines, but only after their commander told him that he should release it as a single did Keith decide to do so.

The song wasn't wholly about 9/11. Keith's father, H.K. Covel, was a veteran, a "Yellow Dog Democrat" in Keith's description, and an outspoken opponent of what he perceived as thin-skinned softness in modern America. His death in a car accident in March 2001 (per CBS News) affected Keith deeply and moved him to become more supportive of active troops through USO tours.

He has an extensive business empire

In 2013, Forbes declared Toby Keith "Country's $500 Million Man." His musical success brought him the cash needed to invest in other ventures, and a name that attracted partners — partners like Don Marrandino, the casino executive who first approached Keith about starting his own restaurant. This wasn't just a case of renting out his name for Keith; he took an active hand in developing the menu and contributed the name, I Love This Bar & Grill (modified from the title of one of his songs). The restaurant grew into a chain, though Keith's involvement and ownership varied from location to location. According to Arizona Central, the chain became marred by abrupt closures and business controversies around 2015, and the official website lists only two remaining locations in Oklahoma.

Keith has had more lasting success with his record label, Show Dog, and its one-time partnership with Scott Borchetta's Big Machine. He has his own liquor label too, Wild Shot mezcal. The income from all these ventures is good enough that Keith's been able to afford the occasional gamble. According to the Herald (via Rob Adams), when a clothing factory near his home in Oklahoma was forced to close, he tried to bring it back in a sustainable way, with no need for himself to turn a profit. Unfortunately, no matter how the numbers were crunched, there was no way for a pair of jeans made in that factory to compete with the price of the imported competition.

He isn't as right-wing as he's made out to be

While speaking to Forbes in 2013, Toby Keith lamented: "Years ago politics branded me as a cat that was an extreme right-wing guy." The nature of many of his lyrics, "Courtesy of the Red, White and Blue (The Angry American)" being only the most well-known, has contributed to his image as a conservative. But Keith has never claimed that label for himself. "I've never been a registered Republican," he told the Chicago Tribune in 2016. In fact, he was a Democrat for most of his life, and his family have been reliable Yellow Dog Democrats except for a preacher brother and, since 2008, Keith himself (per The Boot). Even after he left the Democratic party, Keith registered as an Independent.

Even in the early 2000s, when Keith's lyrics and public statements regarding the war in Afghanistan helped earn him a reputation as conservative, he showed a more independent spirit. He was opposed to the Iraq War, according to the Atlantic, and he voiced no opposition to gay marriage or abortion. In recent years, while he accepted an offer to perform at Donald Trump's preinaugural festivities, he framed the decision as one supporting the office, not the individual, and called Trump (and Hilary Clinton) "media whores" during the 2016 election (via Newsweek). His friend and collaborator Bobby Pinson told the Washington Post that the best political terms to describe Keith were "Toby-crat" and "Toby-can."

He and the Chicks (almost) made up over climate change

"Courtesy of the Red, White and Blue (The Angry American)" brought Toby Keith to a new level of public notoriety. It gave him another hit while also costing him performing opportunities. It also set off a feud between Keith and Natalie Maines of the Chicks, known back in the early 2000s as the Dixie Chicks. Maines not only found the lyrics of "The Angry American" objectionable, but the sort of thing that cast all country music in a bad light, according to the Los Angeles Daily News (via the Top 40 Charts). Keith responded with an unflattering doctored photo of Maines with Saddam Hussein displayed at his concerts, which brought on a riposte from Maines in the form of an insulting t-shirt at the Academy of Country Music Awards, according to Wide Open Country.

For his part, Keith considered the feud over after seeing a friend lose a child to cancer. "It seemed so insignificant," he told the World Entertainment News Network (via Contact Music). "I said, 'Enough is enough.'" Keith and the Chicks would have a chance to publicly make peace in 2008. According to the Mercury News, Al Gore asked them to appear together in a TV spot to raise awareness of global warming. All parties agreed, but when it came time for filming, the Chicks were unavailable when Keith was open, and the idea fizzled out.

He's pals with Stephen Colbert

It's easy to imagine Stephen Colbert, the well-meaning but inept conservative blowhard of "The Colbert Report," listening to country music. But it might not be so easy at first glance to imagine Stephen Colbert, the real-life comedian and Democrat who wears his love for Broadway musicals and J. R. R. Tolkien on his sleeve, having the same appreciation for the genre, let alone Toby Keith's lyrics. But not only is Colbert a fan, he and Keith have formed an unlikely friendship over the years.

According to The Oklahoman, Keith was one of the first musical acts to appear on "The Colbert Report." "I didn't know what to make of the 'boot up your a**' guy," Colbert recalled, "but something down deep told me, 'Just relax, listen to what this man was gonna say and sing, and I just might have a good time.'" After his first appearance on the show, Keith told Colbert, "Hey man, you do a great job, whatever ... it is you do." Colbert loved the remark so much that, for Christmas, his producer gave him a pillow with Keith's words stitched on. Keith went on to make numerous appearances on the "Report" and has since performed on "The Late Show with Stephen Colbert."

For his part, Keith has expressed appreciation that Colbert looked past his media reputation as a right-winger to "get" his music. In 2015, Colbert inducted Keith into the Songwriters Hall of Fame (via Billboard).

His support for cancer organizations

In 2003, according to the Oklahoman, 2-year-old Allison Webb died of kidney cancer. She was the daughter of Scott Webb, a longtime friend and guitar player for Toby Keith. Watching his friend's ordeal, Keith was struck by the stories they had to share of the support and kindness shown them by St. Jude's Children's Research Hospital in Tennessee. "Oklahoma City doesn't have any of these things," said Keith, according to The Boot. That started his charity work helping Oklahoman families struggling with childhood cancer. He helped found the nonprofit Ally's House, named for Webb's daughter, in 2004, and turned his annual Toby Keith and Friends Golf Classic into a fundraiser.

In 2006, Keith established the Toby Keith Foundation to help develop cost-free housing for pediatric cancer patients, and in 2014, the foundation opened the OK Kids Korral. The $20 million facility is situated near The Children's Hospital at Oklahoma University Medical Center and provides lodging for patients and their families. Keith has chosen to narrow the focus of his charitable endeavors to the fight against cancer. "It's nice to have something you're married to, that's your calling," he told The Boot. "Instead of just having your foundation be scattered's like, 'Mine goes over here, to OK Kids Korral."