The Sad Facts About Toby Keith’s Life

Forget apple pie and baseball – America’s true cultural icon might just be the humble red Solo cup. And there’s a man intimately connected to this iconic plastic: Toby Keith.

While Keith may have dismissed his hit song “Red Solo Cup” as “stupid”, it resonated deeply with American party culture. After his passing last February 5, 2024, at the age of 62, fans raised their red cups in his memory, solidifying his place as a musical legend.

But Keith was more than just a party anthem. He was a complex figure, as beloved as he was controversial. He rallied support for the military, wrote patriotic anthems, and embodied the “go big or go home” American spirit. Yet, some of his lyrics were riddled with misogyny, pushing boundaries and sparking debates.

Love him or hate him, there’s no denying Keith’s impact. He soundtracked the lives of countless Americans, from college years to backyard barbecues. But behind the public persona, his journey wasn’t always smooth. Get ready to dive deep into the highs and lows of Toby Keith’s life, a story as messy and vibrant as a Solo cup at the end of a long night.

He learned a lesson on job stability the hard way

In 2013, Toby Keith boasted a net worth of $500 million, earning $48 million annually for several years. But this financial security hadn’t always been his reality. Before conquering the music scene, Keith had experienced the harsh realities of a fickle job market.

At 18, he landed a seemingly secure job in the Oklahoma oil fields, earning a then-impressive $50,000 (equivalent to $213,000 in 2023). However, the oil industry’s volatile nature soon came crashing down. As demand plummeted, the sector plunged into a downturn, throwing hundreds of thousands, including Keith, out of work.

Keith confessed to having saved nothing, leaving him in dire straits. “It about broke us,” he reflected later. “So I just learned… I’ve taken care of my money this time.” He emphasized the fear and uncertainty of that period, stating, “The only constant we had was music.” Despite his musical talent, making it in the industry held no guarantees and seemed like a distant dream.

This unexpected job loss proved to be a harsh but valuable lesson for Keith. It instilled in him the importance of financial responsibility and the unpredictable nature of even seemingly stable careers.

He was rejected by labels because he stayed the way he was

After 1993’s smash hit “Should’ve Been a Cowboy”, Toby Keith’s career appeared destined for smooth sailing. However, his “big break” brought unexpected struggles. While country music drifted towards pop influences, Keith refused to compromise his traditional style.

“They were trying to get me to compromise, and I was living a miserable existence,” Keith told the Associated Press. “Everybody was trying to mold me into something I was not.” After his label repeatedly rejected his songs, Keith felt cornered. In a bold move, he bought out his contract for $93,000, freeing himself but facing an uncertain future.

His decision paid off financially when he signed with a new label, DreamWorks. Yet, fate intervened. DreamWorks acquired his old label, putting him back under the same roof as his nemesis, producer Luke Lewis. The animosity remained, with Keith telling Forbes that he thought the producer hated his music.

Keith’s story highlights the harsh reality artists face when navigating creative integrity and industry pressures. His fight for artistic control, while costly, ultimately paved the way for future success.

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He lost his father in a terrible accident

In 2001, a dark cloud descended upon the country icon’s life with the tragic passing of his father, Hubert Covel Jr. A car accident claimed the life of the family patriarch, leaving a void filled with grief and unanswered questions. While no amount of money could truly compensate for such a loss, a wrongful death lawsuit brought a measure of closure and accountability.

The accident occurred on a seemingly ordinary day in March 2001. Covel was driving home from a gathering when his truck inexplicably veered into oncoming traffic, colliding with a tour bus. Sharing his thoughts with The Oklahoman, Keith said, “I think he had a stroke…Something happened to get him over the median.”

However, the cause of the accident remained shrouded in mystery. The Covel family sought answers, and investigations revealed a disturbing truth: the brakes on the tour bus were faulty due to inadequate maintenance. This revelation led to a lawsuit against Rodriguez Transporters of Tulsa, ultimately resulting in a $2.8 million settlement.

While the legal battle brought a degree of justice, it could never replace the life lost. In the aftermath, Keith penned two poignant songs honoring his father – “Courtesy of the Red, White, and Blue (The Angry American)” and “American Soldier” – solidifying his memory and expressing his grief through music.

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His best friend also lost the battle with cancer

Toby Keith’s life wasn’t just shaped by his own experiences, but also by the profound connections he made. One such bond was with former basketball star and aspiring singer, Wayman Tisdale. Their friendship blossomed through a shared passion for music, with Keith even generously offering Tisdale his tour buses.

News of Tisdale’s tragic passing in 2009 left Keith reeling. Diagnosed with bone cancer after a seemingly innocuous leg fracture, Tisdale succumbed at the young age of 44.

The pain of losing his close friend was further amplified by the circumstances. Tisdale had requested a tour bus, but after days of failed attempts to reach him, Keith learned the heartbreaking truth about his passing.

Grief welled within Keith, prompting him to pen the song “Cryin’ for Me” as a tribute. Unable to sing it at the funeral overcome with emotion, he eventually recorded it, preserving their bond in music. Keith described Tisdale as “the closest thing to Jesus I’ve ever met”, highlighting the profound impact Tisdale had on his life.

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His hometown was struck by a tornado that almost killed his son-in-law

In 2013, tragedy struck Toby Keith’s hometown of Moore, Oklahoma, when a monstrous tornado, packing winds exceeding 200 mph, ripped through the city. Though initially absent, Keith soon returned to survey the devastation alongside Matt Lauer, witnessing the heartbreaking toll it took on his beloved community.

“It was devastating to see,” he expressed on Today, “but it was even worse flying in because I know all these streets… You just look at the devastation.” The storm nearly touched his family personally, as his son-in-law bravely joined the rescue efforts, narrowly escaping death on multiple occasions.

Keith, in an interview with WENN, held immense pride for his son-in-law’s courage amidst the chaos. Despite his truck flipping and suffering electrocution, “[he] ran a nail through his boot,” Keith described.

“He rescues a woman and a kid from a pile of rubble… Then he gets trapped in a flooding tunnel at a schoolhouse, where six kids died.” Despite these harrowing experiences, his son-in-law kept pushing, “trying to help people and trying to dig people out.”

His band tragically lost two key members

Toby Keith’s Easy Money Band has been his musical backbone since his early days. The name itself was born from a lighthearted moment after a $1,000 payday for a high school wedding gig – “easy money”, as he chuckled, and the rest was history.

However, this journey wasn’t without its share of heartbreak. Tragedy struck the band twice, taking away beloved members under unforeseen circumstances. In 2013, the band lost bassist and songwriter Chuck Goff Jr. to a car accident. Still under investigation at the time, an emotional Keith released a statement through The Oklahoman, calling Goff “a close friend for over 25 years” and expressing his deep condolences to the family.

Three years later, the band faced another loss. Guitarist Joey Floyd succumbed to cancer in 2016. In a Facebook post, he acknowledged the void: “There will be a hole on stage and a hole in the hearts of all that loved him.”

Losing both Goff and Floyd undoubtedly left a permanent mark on the band and their fans. While their music continues to bring joy and memories, these tragedies are a stark reminder of the strong bonds forged through music and the lasting impact of those who leave us too soon. 

He was diagnosed with cancer in 2022

In June 2022, Toby Keith stunned fans with a deeply personal message: he had been diagnosed with stomach cancer. His honesty, shared on X, resonated deeply as he revealed six months of treatment and his determination to fight. “So far, so good,” he wrote, expressing his need for recovery and time to heal.

Keith’s openness continued throughout his journey. In September 2023, he spoke with E! News, acknowledging the ups and downs of treatment but emphasizing optimism. “I feel pretty good,” he shared, “a little bit of a roller coaster,” yet he focused on the positive: “I feel good today.”

Early 2024 brought him to The Bobby Bones Show, where he dived deep into his experience. The impact of both COVID and cancer had resulted in a three-year hiatus from performing, and he didn’t shy away from the challenges. Surgery had affected his diaphragm and, consequently, his singing ability. Yet, his spirit remained unbroken.

Keith’s journey serves as a powerful testament to facing adversity with courage and candor. By sharing his struggles openly, he offered strength and inspiration to others battling similar challenges, reminding us that even in the face of hardship, hope and resilience can prevail.

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He shared a hopeful message on Instagram before his death

While Keith had openly shared his cancer battle, his recent performances and upbeat social media presence gave little indication of the impending tragedy. On his final Instagram post, a picture of him holding a guitar to a cheering crowd, he captioned, “And that’s a wrap on the weekend, y’all. Back to it.”

His final television performance, the 2023 People’s Choice Country Awards, showcased his unwavering spirit. He thanked God for strength and even took the stage for a live performance. He continued to perform throughout his final months, headlining a Las Vegas residency and offering words of wisdom to aspiring artists. In a video message, he simply advised, “Just toil away, every day.”

“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.”

Toby Keith’s final stand was a performance in itself. He faced his illness with courage and continued to share his music until the very end. His legacy lives on not just in his iconic songs, but also in the inspiration he offered and the impact he had on countless lives. He truly lived his motto: “And that’s a wrap on the weekend, y’all. Back to it.” And while his music has gone silent, his spirit continues to resonate, forever etched in the hearts of millions.