Toby Keith's Massive Fortune Didn't Just Come From Music

Country music legend Toby Keith died on Monday, February 5, at age 62, reports The Associated Press. The announcement comes about 18 months after the singer made public that he was suffering from stomach cancer. A consummate entertainer to the end, Keith continued to perform while ill, most recently appearing live in Las Vegas for three performances in December 2023.

Hailing from Oklahoma, Toby Keith initially found instant success in 1993 with his debut single "Should've Been a Cowboy" — a song that was reportedly written in a Dodge City, Kansas, motel bathroom. The singer followed up his debut hit with a total of 61 hits on Billboard's Hot Country Songs chart over the course of 19 studio albums that sold more than 40 million copies.

However, Keith proved to be as savvy in business as he was on the stage, accumulating a fortune worth approximately $400 million. Beyond his music, contributing to Keith's impressive net worth was a restaurant franchise, a clothing line, a liquor called Wild Shot, and yes, a record label.

Keith had a penchant for food and drink

One of Toby Keith's most notable endeavors outside of the music industry was his chain of I Love This Bar and Grill restaurants, named after one of his most popular songs, "I Love This Bar." Known for their Southern fare and sprawling guitar-shaped bars, the first I Love This Bar and Grill opened in Keith's home state of Oklahoma in 2005, which was soon followed by one in Las Vegas, Nevada. At the chain's peak of popularity about a decade ago, there were some 20 locations total, although that's since dwindled down to just a few. Though Keith's name and likeness was ever-present inside the eateries, the singer didn't actually own the restaurants. Rather, a franchise model was utilized, with Keith receiving revenue from the naming rights.

Besides the beer served up in mason jars at I Love This Bar and Grill, Keith also was known to have a penchant for mezcal, an agave-derived alcoholic beverage that's a close cousin of tequila. True to Mexican tradition, each bottle of Keith's Wild Shot contains an agave worm (yes, a real insect). Per the product's label, "... the worm is not there for the look, it is there to be eaten. It is believed that the worm will bring a special experience and every individual will feel something different." What Toby Keith feels is rich, because the Wild Shot brand became the bestselling premium mezcal in the U.S. following its 2011 inception and by some accounts, earns approximately $100 million annually.

[Featured image by David Shane via Wikimedia Commons | Cropped and scaled | CC BY 2.0]

A piece of Taylor Swift's success

Not content to limit his success and impressive net worth to the food and beverage industry, Toby Keith also got into the fashion business, launching the clothing line TK Steelman in 2009. Though stylish and inspired by Keith's own wardrobe, it was also important that TK Steelman's garments were affordable enough for the everyman. Finally — and more in line with Keith's area of expertise — much of the country artist's wealth can be attributed to his record label, Show Dog (later Show Dog International). While Show Dog had some modicum of success with artists, such as Trace Adkins, Keith's real coup de grâce was owning a piece of another record label, called Big Machine.

Perhaps more than any of the country star's other entrepreneurial endeavors, Toby Keith's income from his investment in Big Machine had paid off handsomely. How so? The label's roster of artists includes such names as Rascal Flatts, Florida Georgia Line, and at one time, a then-up-and-coming teenage singer-songwriter named Taylor Swift. That's right, every time Taylor Swift sells a record produced during the Big Machine era (until 2018), Toby Keith would receive a small cut.

Considering how he built his fortune through music and beyond, it's no wonder that Forbes once referred to Toby Keith as both a "Cowboy Capitalist" and "Country's $500 Million Man." Not bad for a former roughneck from the oil fields.