Toby Keith, the American country music icon, was valued at $400 million at the time of his death on February 5, 2024, after a battle with stomach cancer. Throughout his career, Keith not only built a vast fortune from music but also diversified his wealth through multiple business ventures, establishing himself as a true mogul in both entertainment and entrepreneurship.
From the early stages of his career, Toby Keith proved he had a unique ability to connect with his audience through storytelling. His debut single, “Should’ve Been a Cowboy,” released in the early 1990s, climbed the charts quickly and became an enduring country classic. This initial success set the foundation for his ongoing dominance in the country music world. Over the years, Keith released a series of hits, including “How Do You Like Me Now?!” and “Beer for My Horses,” the latter being a duet with Willie Nelson. Throughout his career, Keith saw an impressive 60 singles hit the country charts, with 20 of them reaching #1. His talents were also recognized with his induction into the Songwriters Hall of Fame in 2015.
One of the standout features of Toby Keith’s career was his deep sense of patriotism, which resonated strongly with his fans. In the years following the 9/11 attacks, Keith’s music reflected the nation’s collective anger and resolve, particularly in his anthem “Courtesy of the Red, White, and Blue (The Angry American).” While the song stirred some controversy, it highlighted his willingness to use his platform to express his views.
Keith’s entrepreneurial spirit was another key factor in his wealth. He amassed a fortune through various business ventures that earned him more money than his music career ever did. Among his most notable business successes was his chain of “I Love This Bar & Grill” restaurants, which provided a unique combination of good food and country music. Toby’s business interests didn’t stop there; he also invested in Big Machine Records, purchasing a 10% stake in the label for $400,000 in 2004. That decision turned out to be highly profitable as the label went on to sign major acts like Taylor Swift. Keith also maintained a strong philanthropic presence, particularly supporting military veterans through tours and charitable events.
Early Life and Humble Beginnings
Toby Keith Covel was born on July 8, 1961, in Clinton, Oklahoma, the youngest of three children in the Covel family. Raised in Moore, Oklahoma, and Fort Smith, Arkansas, Toby grew up surrounded by music, particularly after spending summers with his grandmother, who owned a supper club. It was there that he first developed an interest in music, and by age 8, he had his first guitar.
Though his childhood was rooted in music, Keith initially focused on football, playing as a defensive end in high school. After graduation, he worked in the oil fields, eventually becoming an operations manager. At 20, Keith formed the Easy Money Band, which played at local bars. Despite his success in the oil industry, he pursued his passion for music, performing regularly with his band. After being laid off from his oil job in 1982, Keith briefly played for the Oklahoma City Drillers, a semi-professional football team, before refocusing on his musical career.
Struggles and Breakthroughs in Music
Keith moved to Nashville in the early 1990s and struggled to get his big break, playing on Music Row and handing out demo tapes to record companies. Despite his efforts, there was no interest in his work, so he returned to Oklahoma. Fate intervened when a flight attendant, a fan of the Easy Money Band, gave his demo to a Mercury Records executive, leading to Keith’s eventual signing.
In 1993, Keith’s career took off with the release of his debut single, “Should’ve Been a Cowboy.” It quickly climbed to number one on the country charts and cracked the top 100 on the pop charts. By the end of the decade, the song had been played more than three million times on the radio, becoming the most-played country song of the 1990s. Toby’s early success set the stage for a series of chart-topping hits and sold-out concerts.
Over the next few years, Keith released several successful albums under Mercury Records, including Toby Keith (1993), Boomtown (1994), Blue Moon (1996), and Dream Walkin’ (1997). In 1998, Keith left Mercury and signed with DreamWorks Nashville, where he released his breakthrough single, “How Do You Like Me Now?!,” which dominated the charts and was the top country song of 2000. His subsequent albums, such as Pull My Chain and Unleashed, all produced multiple number-one hits and achieved multi-platinum certification.
Keith’s work ethic and strong negotiation skills led to several lucrative deals. When DreamWorks rejected several songs from his 1999 album How Do You Like Me Now?!, Keith bought the rights to the album for $93,000 and then flipped them for $200,000. The album went on to sell over 3 million copies, further cementing his status as a country music star.
Concert Earnings and Business Ventures
Toby Keith’s early concert earnings were impressive, earning $20,000 for his first record contract and making $5,000 to $10,000 per night during his 1993 tour. As his music gained traction, his concert fees skyrocketed, and by the middle of the tour, venues were paying him $20,000 per performance. Keith continued to earn substantial money through his tours, further enhancing his financial success.
Keith’s business ventures expanded with his investment in Big Machine Records, which turned out to be a brilliant move. The label went on to sign major artists like Tim McGraw and Taylor Swift. Additionally, Keith opened his “I Love This Bar & Grill” chain, which became one of the top 50 grossing restaurants in the United States by the end of 2004. He also ventured into the alcohol industry, launching Wild Shot Mezcal in 2011, which became the top premium mezcal in the U.S.
Toby Keith married Tricia Lucus on March 24, 1984, and the couple had three children: Shelley, Krystal, and Steven. The couple’s life together was marked by both triumph and tragedy. In 2001, Keith’s father tragically passed away in a car accident, a loss that prompted the writing of his controversial song “Courtesy of the Red, White, and Blue.” On a more philanthropic note, Keith supported various causes, including Little Kids Rock and Ally’s House, a nonprofit organization dedicated to helping children with cancer.
Toby Keith also owned a 300-acre estate, Dream Walkin’ Farms, in Norman, Oklahoma. The estate included a 10,000-square-foot mansion and a professional-level Thoroughbred horse breeding operation. Keith’s ranch also raised livestock, including beef, pork, and turkey, which was sold online.
In 2022, Keith revealed that he had been diagnosed with stomach cancer. After a courageous battle, Toby Keith passed away on February 5, 2024, at the age of 62. His legacy, both as an artist and an entrepreneur, will continue to influence future generations.
