5. Johnny Mathis ($400,000,00)
Hey look at that, there’s an actual male in the top 5. Surprisingly enough, this is also the first person on this list that decided to do something with their money instead of just maintain the routine. Mathis is an expert investor, as he owns a chain of restaurants and an actual football team.
He’s also well-versed in fashion and has released a line of his own, while staying true to his investing nature as a stockholder. Of course, a guy never made $400,000,000 by singing (well, aside from Michael Jackson).