The Lesser-Known Truth Of Toby Keith

Country music fans are mourning the loss of Toby Keith, who died on February 5, 2024, at age 62, after a long battle with stomach cancer. During a music career spanning four decades, the singer-songwriter charted more than 60 singles, ranging from his 1993 breakout, "Should've Been a Cowboy," to classic hits such as "Red Solo Cup," and "As Good As I Once Was." During those years, Keith carved out his own unique niche in country music while also becoming one of the genre's most successful artists; at one point, he amassed a net worth estimated at a cool half-billion dollars. 

Keith was also a top concert draw, an entrepreneur, and a philanthropist, mounting a benefit concert to fund relief efforts after a devastating tornado in his home state of Oklahoma. He also served Oklahomans through his namesake foundation, which launched the OK Kids Corral for children undergoing treatment for cancer. Just months before his death, Keith was asked to identify which aspect of his career he felt most proud of. "My songwriting," he told E! News. "Those years of pounding those songs out there and remembering where you were when each one was conceived and all that, it's amazing."

As fans fondly remember this multitalented artist, we're looking at all the things that may have been forgotten over the years. Keith's rich life didn't just include music, but also sports, politics, business, and strong Oklahoma roots.

Toby Keith spent his formative early years immersed in music. Much of that was due to his grandmother, whom he immortalized in his autobiographical 2005 hit "Honky Tonk U." In the single, he sings about spending a summer working at her nightclub in Fort Smith, Arkansas, recalling how she'd let him "sneak out of the kitchen and sit in with the band."

Interviewed by The Oklahoman in 2011, Keith reminisced about the time he spent in her watering hole, Billy Garner's Supper Club. "It was a supper club, and they don't even really have 'em anymore," he explained. "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," he added. For Keith, watching the club's band perform was a seminal experience, rousing his interest in a music career. "I stayed the whole summer ... and I watched that band play, and I knew that I had to find my way onto that bandstand," he said.

Another of Keith's songs, the 2011 single "Clancy's Tavern," also pays tribute to his grandmother and her club. "The song is true," he told the Columbus Dispatch, "right down to her taking her pistol and the money to the bank." 

Growing up in small-town Oklahoma, Toby Keith's father and grandfather both worked in the state's oil fields. After graduating from high school, Keith continued the family tradition by taking a job in the oil industry. He proved to have a knack for working with oil derricks, and eventually worked his way up to operation manager. 

As Keith recalled in an appearance on "The Big Interview" with Dan Rather, the work was gruelling and unrelenting. "Service companies like we were in were 24/7, and you go out three days, you come back and you sleep when they're filling the mud," he said. "They'll take and fill a casing with mud and that's your 30-minute nap. And you just go, and at 18 years old, it made me a man."

It was while working in the oil fields that Keith met his wife, Tricia Lucas, who was working as a secretary for an oil company. "I was 19 and he was 20," she told People. "He was just one of those larger-than-life guys, full of confidence." Once Keith began focusing on music, which required him to be away from home a lot, there wasn't much of an adjustment for the couple. "When we met, I was already busting my hump, working in the oil fields, so I was gone three or four days a week anyway," Keith told The Palm Beach Post.

While growing up, football had been a passion for Toby Keith. While attending Moore High School, Keith played defensive end for the school football team. While he didn't play college ball — because he never went to college — Keith maintained his gridiron skills over the years, so much so that he embarked on a brief career playing semi-professional football. 

When he found himself out of a job when the oil industry slowed down in the 1980s, the 6-foot-3-inches Keith tried out for a spot on the Oklahoma City Drillers and was hired to play on the team. The Drillers were a semi-pro outfit that served as a sort of unofficial farm team for the Oklahoma Outlaws, part of the short-lived United States Football League (Keith tried out for the Outlaws, but didn't make the cut). Playing football during the day, Keith spent his nights performing music in local honky-tonks, pursuing music and football simultaneously. Keith ended up playing for the Drillers for just one season, in 1982. Later, Keith dedicated himself to writing songs and performing, but it wasn't easy. During those early years as a professional musician, "it was about four years of starving," he told The Birmingham News in 1993.

Since his breakout days in country music, Toby Keith has been backed by the Easy Money Band. The origins of the band's name go back a long way, dating to when he was a recent high school graduate. At the time, Keith and his band landed a big gig that offered a hefty paycheck. "We played a wedding and somebody gave us $1,000," Keith told Billboard, "and that's where the band came up with the name 'Easy Money.'"

While Keith and the band would eventually end up earning a lot more than a thousand dollars a gig, there were some lean years at the start. In fact, $1,000 may have seemed like an astronomical sum during the years that Keith worked on oil derricks and peformed in honky tonks in his spare time. "After we went to the taverns, it was $35 a man a night, plus your beer," Keith recalled. 

Everything changed for Keith and the Easy Money Band when a flight attendant named Lori Hardin — who'd become a big fan of the group — played one of Keith's CDs for an influential music executive. Intrigued and excited by what he heard, the exec tracked down Keith and signed him to a record deal. That led to the release of his debut single, "Should've Been a Cowboy," which rocketed to No. 1, establishing him as a rising star in the country music scene.

In 2001, Toby Keith's father, Hubert "H.K." Covel Jr., was killed in a tragic car accident. Later that same year, Keith watched in horror as hijacked airplanes struck the World Trade Center's twin towers. Those two events, though unconnected, combined to provide Keith with inspiration for a new song, his 2002 hit "Courtesy of the Red, White and Blue (The Angry American)."

As Keith recalled during a media event, as reported by The Boot, his father was a veteran who'd lost an eye while serving his country. "And I thought, man, when those buildings came down, he would be really angry," Keith said of his late father. "[My dad] was a true patriot: He never complained about his eye. He never complained about the time he served or how they treated him after. He just went back to work. He was just a good, old, solid cat."

He debuted the song while performing for some Marines at the Pentagon, and the response he received was through the roof — but at the same time, he knew the angry tone would drum up controversy. "And so I prayed about it and discussed it with everybody for a long time, because I knew it was going to cause a storm," he said. "But at the end of the day, I was like, 'If it means that much to those guys, then I don't care. I'll do it.'"

As predicted, "Courtesy of the Red, White and Blue" was controversial, expressing Toby Keith's desire to retaliate for the 9/11 terror attacks with lyrics like, "We'll put a boot in your ass, it's the American way." Natalie Maines, lead singer of The Chicks (then known as Dixie Chicks) was particularly critical. "I hate it," she told the Los Angeles Daily News (via CMT). "It's ignorant, and it makes country music sound ignorant." Keith subsequently offered a dismissive retort. "I'm a songwriter. She's not," Keith told CMT. "She can say my song is ignorant, then it's ignorant for her to say that because she's not a songwriter."

Maines and The Chicks were later hit by backlash over some disparaging comments she made about then-president George W. Bush, with country radio banning their music for what was perceived as Maines' lack of patriotism. The situation only fuelled public speculation about the Maines-Keith dustup. 

Keith eventually buried the hatchet. "I'm embarrassed about the way I let myself get sucked into all of that. I disappointed myself," he told reporters, as reported by CMT. Admitting he'd gone too far by putting images of Maines alongside Saddam Hussein on video screens during his shows, he added, "I just said, 'You know what? She's getting kicked enough without me piling on.' She would have the same thing she got without me even saying a word. I'll know better. I'll learn something next time... Maybe."

When Toby Keith's father, Hubert "H.K." Covel Jr., was killed in a 2001 car wreck — his vehicle jumping the median and then getting hit head-on by a bus — Keith initially suspected a heart attack was behind the accident. However, an investigation subsequently revealed that another motorist had struck Covel's truck, which may have caused it to go over the median. The woman who was behind the wheel pleaded guilty to leaving the scene of an accident and received a one-year deferred sentence. Further investigation revealed that the bus that struck Covel's vehicle was not mechanically sound, and was sorely in need of significant work on its brakes.

Keith and his family sued the company that owned the bus, Rodriguez Transportes. The wrongful death lawsuit alleged that Covel wouldn't have been killed had the air brakes on the bus been functioning as they should have. Several years later, the case went to trial. When it was all over in 2007, the jury found the company at fault for Covel's death. Keith and his family were awarded damages of $2.8 million. The company appealed but to no avail. Several years later, in 2012, the Oklahoma Supreme Court affirmed the original verdict.

Alongside his successful career in country music, Toby Keith also dipped his toe into the world of acting. Keith made his movie debut with a starring role in the 2006 drama "Broken Bridges," playing a washed-up country singer who returns to his hometown, where he reunites with his high school sweetheart and meets his teenage daughter for the first time.

He then starred in the 2008 comedy crime caper "Beer for My Horses," the title loosely inspired by his hit song of the same name, co-starring with comedian Rodney Carrington. Described as "an abysmal 2008 vanity project" by The Atlantic, "Beer for My Horses" managed the rare feat of earning a zero percent score on Rotten Tomatoes. After that, Keith stepped away from movies and returned his focus to music. 

In addition to acting, Keith also had a brief flirtation with professional wrestling. In 2002, Keith performed "Courtesy of the Red, White and Blue" during a TNA pay-per-view event — only to have his song rudely cut short by wrestler Jeff Jarrett. Keith returned the favor later that evening when he barged in on Jarrett's match and proceeded to execute a suplex on him.

Any Swifties worth their salt know that Taylor Swift's big break came when she was signed to Scott Borchetta's record label Big Machine back in 2005. What they might not be aware of, however, is that Big Machine was initially the result of a joint venture Borchetta entered with Toby Keith, who was reportedly instrumental in signing Swift. Keith eventually broke away from Big Machine in 2006 but maintained equity in the company. 

Early on in Swift's career, shortly after signing with Big Machine, she discussed her admiration of Keith. "You're in the room with him and you can feel it. There's a power there, and you're just like 'Oh my God,'" Swift told Nashville's WSMV. "I don't think I'll ever get to a point where I won't see him and be like, 'Oh my God, that's Toby Keith!'" 

When Keith was inducted into the Songwriters Hall of Fame, it was Swift who introduced him. "Hey Toby! It's Taylor! Remember me?" she said in a video recorded for the occasion. "Last time you saw me I was like 15, had crazy curly long hair. Wore cowboy boots and like prom dresses everywhere. A lot has changed in the last 10 years, but you introduced me at the Country Radio Seminar back in 2005, and I wanted to say thank you for doing that."

In 2005, Toby Keith got into the restaurant business when he opened Toby Keith's I Love This Bar & Grill in Oklahoma City, the eatery's moniker taken from his 2003 single "I Love This Bar." More locations followed in cities throughout the U.S. and at its peak, the chain boasted 20 locations. As of 2024, however, there were just two restaurants left: one in Oklahoma City, and another in Keith's hometown of Moore, Oklahoma.

So what happened? As AZ Central reported in 2015, 17 of the 20 restaurant locations went under in 2014 and 2015, and plans for restaurants in 19 other cities were scuttled. In addition, the chain was hit with lawsuits, judgments, and various liens in 24 different cities, to the tune of $28.6 million.

The problem had nothing to do with Keith — who'd merely leased the use of his name to the venture — but with the company that ran the restaurant chain, Boomtown Entertainment. Boomtown was accused of accepting millions of dollars from malls and developers to open new restaurants and then walking away with the cash. To make matters worse, the company was accused of not paying its suppliers or its sales tax. It was later revealed that Boomtown was owned by Frank Capri, an alleged mobster, while the company's vice president and legal counsel, Gregory McClure, was charged with embezzling and money laundering. 

Toby Keith's now-defunct restaurant in Las Vegas was the launch site of another business venture when, in 2009, Keith unveiled his own clothing line, TK Steelman. The casual fashion brand included t-shirts (including long-sleeved and sleeveless varieties, the latter reflecting Keith's tendency to rip the sleeves off his own shirts), sweatshirts, polo shirts, jeans, boots, baseball caps, belts, bandanas, and other items.

The clothing line came about through an existing partnership between Keith and Royal Merchandising Group, which produced an array of merch for the restaurant chain. The TK Steelman line was targeted at males aged 25 to 54, and sold at various U.S. retail outlets, including Walmart, Macy's, and Target, in addition to being sold at Toby Keith's I Love This Bar & Grill. "The look mixes the influences Keith brings to his own wardrobe — part rocker and part biker with a 'country sexy' aesthetic punctuated by oilfield imagery in the brand's logos and font selections," declared a press release, via Fibre2Fashion.

One of Keith's biggest priorities with TK Steelman was to design jeans that offered both comfort and style. "I have to be comfortable in my jeans," he told The Oklahoman. "They have to fit just right, not too baggy, so I worked the designers hard on that, and they did a great job, I think, on the jeans. I love them."

Toby Keith was often branded as a right-wing conservative, in large part due to the controversy garnered by his 2002 track "Courtesy of the Red, White and Blue (The Angry American)." In truth, however, his political views were not nearly so cut-and-dry. As The New York Times recalled, he'd told Playboy he was once a registered Democrat — albeit "a very conservative Democrat" — before registering as an independent. Still, Keith didn't give too much credence to how his politics tended to be depicted in the media. "Most people think I'm a redneck patriot," he told Time in 2004. "I'm okay with that."

During a 2009 interview with CNN, Keith was asked to pinpoint the most prevalent misconception that people have about him. "That I'm a lifetime Republican, right-wing Nazi guy. If that's their perception of me, that's fine," he said. Noting the political polarization that had taken hold within American politics, he sarcastically added, "But you can't support the troops and be for national health care; that's illegal in this country. You're either right or you're left, buddy."

In 2017, he addressed the backlash he'd received for performing at Donald Trump's presidential inauguration. "I don't apologize for performing for our country or military," he said in a statement to Entertainment Weekly. "I performed at events for previous presidents [George W.] Bush and [Barack] Obama and over 200 shows in Iraq and Afghanistan for the USO."

Toby Keith had grim news for fans in a June 2022 Instagram post. "Last fall I was diagnosed with stomach cancer," Keith wrote, noting that he'd undergone surgery and was being treated with radiation and chemotherapy. "So far, so good," he wrote of the progress of that treatment.

Keith laid low for the next year or so, but broke his silence in a June 2023 interview with The Oklahoman to offer an update. "I'm feeling pretty good. ... Basically, everything is in a real positive trend. You never know with cancer, so you have to prepare," he said. He also revealed that his progress had been significant enough that he was considering returning to the stage, albeit on an experimental basis, once he'd regained enough strength to perform. "But my goal is, I feel better; I've got more wind," he told the newspaper. "And I'm thinking about bringing the band in and setting up, playing two or three days somewhere just to see if I can get through two hours."

He later spoke with CMT Hot 20 Countdown about his potential comeback but admitted the treatment he'd received had taken a toll on him. "It's pretty debilitating to have to go through all that ..." he conceded, but also expressed confidence he'd return to the stage soon. "I'm thinking about getting back in fighting shape," he said. "I need a little time to just rest up and heal up."

In the middle of 2023, Toby Keith tested the waters when he took to the stage at Hollywood Corners — a small music venue he owned in Norman, Oklahoma — for a pair of secret pop-up shows. He followed that up a few months later in October 2023, when he made a surprise appearance at Jason Aldean's show in Oklahoma City, with the two performing a duet of Keith's "Should've Been a Cowboy."

Those onstage jaunts went well enough that, the following October, he announced he'd be performing some bona fide concerts in Las Vegas that December. "It'll be my first two shows," he said in a video he posted on YouTube. "They're kind of rehab shows — get the band back in sync, get me rolling again," he added. Those two shows sold out within minutes, and a third was added, all taking place at Dolby Live at Park MGM. 

During one show, he addressed the audience. "You think I'm dying, don't you?" he said, as reported by Music Mayhem. "Me and the Almighty got this, we're good, y'all!" After the first show, Keith shared his thoughts via Instagram. "It was a triumphant return," he wrote. "One hell of a night in Vegas." In a subsequent Instagram post, Keith reflected on what would, sadly, be his final concerts before succumbing to cancer less than two months later. "[Three] sold-out shows in Vegas was a damn good way to end the year," Keith wrote.