The Tragedy Of Toby Keith's Real-Life Story

America loves to take credit for inventing things, and the whole "go big or go home" idea definitely applies. Whether or not it's true is a different thing entirely: Apple pie is, after all, English, while baseball? That's complicated, but also, it's very British. But what America does have a rightful claim to is red Solo cups. They got their start in the 1970s, and the Illinois-based company actually had a few colors including peach, yellow, and, of course, red. That brings us to Toby Keith, who was onto something ... even if he didn't quite appreciate it at the time.

Everyone who's ever been to a party in the U.S. — or even in the general vicinity of one — knows what it means when the red Solo cups come out, but in 2014, Keith told The Boot: "It is the stupidest song I ever heard in my life, but it's so stupid it's good." And that's what music should be, right? That's probably why fans across the country raised their red Solo cups after learning about his death in 2024.

Keith was as controversial as he was popular, rallying military support in the wake of 9/11 while at the same time raising questions about how far was too far. There were his party songs and the songs that got attention for leaning a little too far into the misogyny, as well as plenty of unabashed patriotism topped with a ten-gallon hat. It's still undeniable that he was the soundtrack of college years and block parties, but for him, it wasn't an easy road.

In 2013, Forbes got up close and personal with Toby Keith, saying that he was worth somewhere upwards of $500 million, and that he'd spent the previous five years making more than $48 million annually. But Keith also knew what it was like to be on the other side of the income scale, and success hadn't happened overnight.

It had, in fact, come after some devastating setbacks. Before becoming a singer, he was both a semi-pro football player and a worker in the Oklahoma oil fields. He started there at the end of 1979, and became an 18-year-old making a whopping $50,000 a year. (Adjusted for inflation, that's about $213,000 in 2023.) Not bad? It was incredibly short-lived, and when demand for U.S. oil started dropping, the industry started to fail. By the time things stabilized, hundreds of thousands of people were out of jobs ... including Keith. 

Keith later told the Associated Press (via Fortune) that he hadn't saved a penny — and that meant he found himself with next to nothing. "It about broke us. So I just learned. I've taken care of my money this time," he explained, stressing that it was a turbulent, uncertain, and frightening time. "All through this whole thing the only constant we had was music. But it's hard to sit back and say, 'I'm going to make my fortune singing music, or writing music.' I had no contacts."

Once an artist is signed to a label — and has a hit or two under their belt — it's smooth sailing ... right? Not exactly, and Toby Keith has been pretty straightforward about struggling after he had a massive hit with 1993's "Should've Been a Cowboy." Even though it was considered his big break and remained the most popular country song of the decade, he found himself facing something of a crisis.

At the time there was a shift in country music, which was becoming less traditional and more pop-inspired. Keith had no interest in going in that direction, but felt overwhelming pressure from his record label to do exactly that. In an interview with the Associated Press, he explained (via Fortune), "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."

By 1999, his label had continued to reject songs, and Keith felt he had no choice but to spend $93,000 to buy out his contract. He made a fortune when he jumped to another, more accommodating record label, but in between, he said he felt trapped in a nightmarish career that got worse. After leaving Mercury, following a feud with producer Luke Lewis, he switched to DreamWorks ... but when DreamWorks acquired his old label, he found himself working with his old nemesis again. And it was clear how Lewis felt: Keith told Forbes he thought it was clear that Lewis detested his music.

The life of a beloved parent is priceless, but after a tragic 2001 accident took the life of Toby Keith's father, Hubert Covel Jr., the Covel family learned just how much the life of their patriarch was worth: $2.8 million. The verdict was announced after a lawsuit found that Rodriguez Transporters of Tulsa was responsible for the accident, and it's a terrifying thing to have to face.

The incident happened in March 2001, when Covel was driving home from a friend's BBQ. He was pronounced dead on the scene after his truck crossed into oncoming traffic and collided with a tour bus, leaving the family to wonder just what had happened. Keith spoke with The Oklahoman, saying, "I hate to speculate, but I think he had a stroke. It was early part of the afternoon, time for him to cat around." Keith also noted that he'd had major heart surgery a few years prior, adding, "Something happened to get him over the median. He was only going 35 mph. He was too good a driver."

The courts agreed that something wasn't right, and it was discovered that the bus that collided with Covel hadn't been properly serviced, and that the brakes were faulty. The wrongful death suit found in favor of the Covels, but it's safe to say that no amount of money can bring back a beloved father, immortalized in "Courtesy of the Red, White and Blue (The Angry American) and "American Soldier."

Real friends aren't just one in a million, they're worth their weight in gold. For Toby Keith, former basketball star Wayman Tisdale was one of those friends, and when he was diagnosed with bone cancer after breaking his leg, Keith was there for him. Tisdale was transitioning into a singing career and bonded with Keith over it, and the two got to be such good friends that Keith would give him use of his tour buses when he went out on the road.

That ended up being how he found out about his passing. On a video for his Facebook page, Keith shared the sad story: Tisdale had asked if he could use the bus, and given him considerable notice. The requested weekend neared, Keith couldn't get in touch with him, and after days of trying, he found out that he had passed away. "I didn't believe it," Keith said. "I called his phone back, and I got his voice message. And it always said, 'Have a nice day. Have a blessed day.'"

"Cryin' for Me" was written for Tisdale's funeral, but Keith said he just couldn't bring himself to sing it — he tried while his wife was driving him to the service, but could never finish the song. He ended up recording it, and later told The Boot: "He was a great guy with a charismatic smile, and the closest thing to Jesus I've ever met." Tisdale was 44 years old at the time of his 2009 death.

In 2013, a massive tornado tore through the center of Moore, Oklahoma. "Massive" is in no way an understatement: It was the worst-case scenario, with winds over 200 mph. Toby Keith wasn't there to see the tornado tear through his hometown, but soon after, he and Matt Lauer walked through what remained of the areas hardest hit.

"It was devastating to see, but it was even worse flying in because I know all these streets," he told Today. "... There's a lot of places it could have come across, and this is where it came across. You just look at the devastation." Keith also said that he very nearly lost a member of his own family: His son-in-law was part of the rescue efforts, and suffered through a few potentially deadly incidents, including electrocution.

In an interview with WENN (via the Winnipeg Sun), Keith spoke about just how proud he was that his son-in-law had headed out to brave the deadly storm to help anyone he could. Even after his truck flipped over and the electrocution incident, Keith said, "[he] ran a nail through his boot. He rescues a woman and a kid from a pile of rubble. Then he gets trapped in a tunnel that was flooding with water at a schoolhouse, where six kids died." He then nearly got crushed by an ambulance, but Keith was proud to say that he kept "trying to help people and trying to dig people out."

Toby Keith's Easy Money Band has been with him since the start of his music career. He explained to Rolling Stone that the name came to him after he — right out of high school — was given $1,000 for playing at a wedding. Easy money, he thought, and the rest is history. Over the years, he's had to say goodbye to two band members under tragic circumstances.

In 2013, bassist and songwriter Chuck Goff Jr. was killed in a car accident. It was being investigated at the time of the announcement, and in a statement via The Oklahoman, Keith said, "He was a close friend for over 25 years, the band leader and bass player. Our hearts and prayers go out to his family."

Then in 2016, Keith posted a Facebook video tribute to another bandmate, Joey Floyd. The video of the on-stage performance was accompanied by, "Our brother Joey has passed away. He is now free of all pain. He will be missed forever. Rest in peace little buddy." In another post, Keith wrote, "There will be a hole on stage and a hole in the hearts of all that loved him." The official cause of death was cancer.

On June 12, 2022, Toby Keith posted a very personal message on X (formerly known as Twitter): He revealed that he had been diagnosed with stomach cancer, and had been going through treatment for the previous six months. "So far, so good," he wrote. "I need time to breathe, recover and relax." Stomach cancer is relatively rare, and the American Cancer Society says that only about 1.5% of new cases of cancer diagnosed in the U.S. annually are stomach (or gastric) cancer.

Keith remained candid but optimistic, and in September of 2023, he spoke with E! News about the announcement that he was the People's Choice Country Awards recipient of the Country Icon Award. His cancer was responding to treatment, and he said, "I feel pretty good. 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."

Then, in early 2024, he appeared on the Bobby Bones Show to talk a little about everything — including his diagnosis, treatment, and the long-lasting impacts he experienced. Keith revealed that between Covid and cancer, he went about three years without performing and said that, yes, it was difficult. He had undergone stomach surgery that also impacted his diaphragm and, by extension, his ability to sing. Still, he remained hopeful.

When Toby Keith passed away on February 5, 2024, it's safe to say that it was a shock. Although he had been candid about his health issues, his cancer diagnosis, and his treatment, he had also been performing before sold-out audiences in the months leading up to his death. In fact, his final Instagram post came on the same day as his death: In it, Keith faced away from the camera and held up his guitar to a cheering concert crowd. It was captioned with a now-eerie message: "And that's a wrap on the weekend, y'all. Back to it."

Keith's final television performance was at the People's Choice Country Awards in September 2023, when he thanked God for the strength he'd found during his treatments. He also performed live in December that year, where he headed a series of three Las Vegas shows. Also in his final months, he shared some advice for aspiring singers and songwriters, posting a video message on X (formerly known as Twitter) saying, "Just toil away, every day."

Tributes poured in after his passing, and were perhaps best summed up by Old Dominion. They wrote on X, "Toby Keith was a true trail blazer. Authentic and heartfelt but always with a wink 'til the end. He was larger than life in so many ways and his much will live on forever! Raising our red solos tonight — you will be missed by so many. Peace."