Country music fans know Toby Keith for his patriotic anthems, love songs, and borderline comedic redneck songs, but he was also a formidable businessman and entrepreneur, earning him Forbes notoriety as a “500 Million Dollar Man.”

The “I Wanna Talk About Me” singer invested in and started many businesses, including a bait and tackle shop called Luck E Strike. Luck E Strike appeared to be brought back to life by Keith’s investment in 2023. The singer took his love for singing about the country to his pocketbook with this investment, according to Fox Business.

His “I Love This Bar” song took on a new meaning with a bar sporting the song name. His bar currently has two locations and is a big draw to his bar-hopping fans.

Keith’s love for horses really showed through his investment in Dream Walkin’ Farms, which trained racehorses. The farm’s horses brought in 850 wins, according to Equibase. He was known for his love for horses and sang about it in his hit song, “Beer for My Horses.”

Another business venture that Keith took part in was Big Dog Cannabis. The “How Do You Like Me Now” singer started this business from the ground up. It licensed cannabis flowers, edibles, and pre rolls according to Fox Business.

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The “Red Solo Cup” singer also had a Mezcal alcohol business called Wild Shot.

Those business investments added to his fortune, but his music was still an important part of his overall financial picture. According to the Songwriters Hall of Fame, Keith has brought in over $40 million in song sales.

Keith also owned Show Dog Records, which had a relationship tie to Big Machine Label Group. It recently disbanded according to Music Row.