Waylon Jennings (Deceased – $7 million)
Best known for making outlaw country music popular, Waylon Jennings used heavy rock influences and gritty notes to electrify his tunes. He used to be in The Highwaymen with other legends like Johnny Cash, Willie Nelson, and Kris Kristofferson. His son said that he was full of joy and creativity, and Kristofferson said that he was rough on the outside but soft on the inside. He passed away in 2001.
Waylon Jennings (Deceased – $7 Million)
Toby Keith ($365 million)
In 1993, Toby Keith released his first album. “How Do You Like Me Now?” was in the 1998 album that he worked on with DreamWorks Records. “Should’ve Been a Cowboy,” on the other hand, was the most-played song in the genre in the ‘90s! He ended up launching a record label of his own called Show Dog Nashville after DreamWorks shut down. In 2009, he renamed it Show Dog-Universal Music.
Toby Keith ($365 Million)
