Waylon Jennings (Deceased – $7 million)
Best known for making outlaw country music popular, Waylon Jennings added heavy rock influences and gritty notes to his songs. He used to be in a country music group called the Highwaymen with Willie Nelson, Kris Kristofferson, and Johnny Cash. According to his son, he was full of joy and creativity. Kristofferson, on the other hand, said that he was tough on the outside but soft on the inside. He died from diabetes complications in 2002. The year before that, he entered the Country Music Hall of Fame.
Waylon Jennings (Deceased – $7 Million)
Toby Keith ($365 million)
Are you aware that Toby Keith is one of the wealthiest people in the country music scene? In 1993, he released his first album that he followed up with three more. The “How Do You Like Me Now?” singer was also the man behind the most-played ‘90s country hit: “Should’ve Been a Cowboy.” After DreamWorks Records shut down, he founded a record label under the name Show Dog Nashville. In 2009, it was renamed to Show Dog-Universal Music and has since signed many big names in the genre.
Toby Keith ($365 Million)