8. Toby Keith ($360,000,000)
Wouldn’t you know it, there’s another dude here. This one though doesn’t invest into anything. Toby Keith is what you get when you subtract a Y and add an X chromosome to the fetus of Dolly Parton. No, take that literally. They are fabled for the exact same kind of versatility, singing genre and career paths.
The only thing that makes Toby slightly different is the fact that he’s, well, younger. He could not have starred in grainy 70’s YouTube videos because he was only a mere teenager then. Seeing how the world is today, he could’ve been big now if he were born in 2005.