The Lesser-Known Truth Of Toby Keith

Country music fans are reeling from the loss of Toby Keith, who passed away on February 5, 2024, at the age of 62, after a prolonged struggle with stomach cancer. His music career, which spanned over four decades, was marked by more than 60 charted singles, showcasing hits like "Should've Been a Cowboy," "Red Solo Cup," and "As Good As I Once Was." Not only did Keith create a distinctive niche in country music, but he also became one of the genre's most prosperous artists, with a net worth estimated at around half a billion dollars.

Beyond being a top-charting artist, Keith was a dynamic concert performer, a savvy entrepreneur, and a philanthropist who organized benefit concerts for tornado relief in Oklahoma. His namesake foundation, which opened the OK Kids Corral for children battling cancer, showcased his dedication to giving back. When asked what he was most proud of in his career, Keith expressed, "My songwriting. Those years of pounding those songs out there and remembering where you were when each one was conceived, it’s amazing."

As we celebrate the life of this multifaceted artist, we reflect on the many aspects of his journey that may not be widely known—his deep ties to music, sports, politics, and business, all rooted in his strong Oklahoma upbringing.

Table of Contents

• Biography of Toby Keith
• His Grandmother's Supper Club Led to His Love of Music
• Toby Keith Worked in the Oklahoma Oil Fields
• He Was a Semi-Professional Football Player
• An Early Gig Playing a Wedding Inspired the Name of His Easy Money Band
• The Death of His Father and a Terrorist Attack Combined to Inspire a Beloved Patriotic Hit
• Toby Keith Feuded with The Chicks' Natalie Maines
• He Won Millions in a Lawsuit Involving His Father's Death in a Car Accident
• Toby Keith Dabbled in Acting (and Pro Wrestling)
• Toby Keith Was Instrumental in Taylor Swift's Big Break
• Toby Keith's Restaurant Chain Brought Him Grief — and Lawsuits
• He Launched His Own Clothing Line
• His Political Views Were More Nuanced Than They Appeared
• He Shocked Fans When He Revealed His Cancer Diagnosis
• His Final Concerts Were Pure Triumph

Biography of Toby Keith

His Grandmother's Supper Club Led to His Love of Music

Toby Keith's musical journey began in his early years, significantly influenced by his grandmother. He often reminisced about spending summers at her nightclub in Fort Smith, Arkansas. In his autobiographical song "Honky Tonk U," Keith reflects on how she allowed him to "sneak out of the kitchen and sit in with the band," igniting his passion for music.

In a 2011 interview, Keith described the supper club as a unique establishment—a tavern serving beer in the front and fine dining with live music in the back. This experience was pivotal for him, as he stated, "I stayed the whole summer... and I watched that band play, and I knew that I had to find my way onto that bandstand."

Toby Keith Worked in the Oklahoma Oil Fields

Growing up in a small town, Toby Keith was steeped in the oil industry, following in the footsteps of his father and grandfather. After high school, he took a job in the oil fields and quickly advanced to an operation manager role. He described the grueling nature of the work, revealing that the experience significantly shaped his character as a young man.

Keith's time in the oil fields also led him to meet his future wife, Tricia Lucas. Their relationship began amidst the challenges of the oil industry, which prepared them for the transitions that would come as Keith moved towards a career in music.

He Was a Semi-Professional Football Player

Before his rise in the music industry, football was a significant passion for Toby Keith. He played defensive end in high school but didn't continue in college. However, as the oil industry waned in the 1980s, he pursued semi-professional football by joining the Oklahoma City Drillers.

During his time with the Drillers, Keith balanced his day job with performing music at local honky-tonks, showcasing his determination to succeed in both fields. Despite playing only one season, his experience in football laid the groundwork for his disciplined work ethic as a musician.

An Early Gig Playing a Wedding Inspired the Name of His Easy Money Band

The Easy Money Band, which backed Toby Keith during his early career, got its name from a memorable gig. After a successful wedding performance where they received a $1,000 payment, Keith remarked, "That's where the band came up with the name 'Easy Money.'" This early success was a promising start for the group, but it wasn't always easy sailing.

Although the band would eventually earn significantly more per gig, the struggles of early performances were real, as Keith often shared stories of the lean years where they earned just $35 a night plus drinks. However, this experience taught him the value of hard work and persistence in the music industry.

The Death of His Father and a Terrorist Attack Combined to Inspire a Beloved Patriotic Hit

The tragic death of Toby Keith's father in 2001, coupled with the 9/11 terrorist attacks, became the backdrop for one of his most famous songs, "Courtesy of the Red, White and Blue (The Angry American)." The song was inspired by his father's patriotism and the anger Keith felt in response to the attacks.

Keith described how he believed his father would have reacted angrily to the events of that day, which fueled his songwriting process. He debuted the song to an enthusiastic audience of Marines at the Pentagon, knowing that its bold message would stir controversy but feeling compelled to share it nonetheless.

Toby Keith Feuded with The Chicks' Natalie Maines

His song "Courtesy of the Red, White and Blue" ignited a public feud with Natalie Maines of The Chicks, who criticized the song for its aggressive tone. Keith responded by asserting his identity as a songwriter, indicating that Maines' opinions did not define his artistic expression.

This conflict was heightened by Maines' own controversial comments about then-President George W. Bush, leading to a backlash against her and the band. Over time, Keith reflected on the feud, recognizing that he had let himself become too embroiled in the conflict and ultimately sought to mend fences.

He Won Millions in a Lawsuit Involving His Father's Death in a Car Accident

Following the tragic death of his father, Toby Keith and his family pursued a wrongful death lawsuit against the bus company involved in the accident. They argued that the bus's malfunctioning brakes were a direct cause of the fatal incident, ultimately winning $2.8 million in damages after a lengthy trial.

The case highlighted the importance of accountability in such incidents, as Keith's family sought justice for their loss. The outcome not only brought financial relief but also served