David Letterman (1947), Indiana | $50M

David Letterman is a legendary American TV host, producer, and writer. He is known worldwide for hosting the popular show “The Tonight Show” for 33 years. Letterman has interviewed some of the top-rated gems in the industry globally. He has won awards such as two Daytime Emmy Awards, ten Primetime Emmy Awards, and four American Comedy Awards.

From 2018 to 2019, he started hosting the Netflix interview show “My Next Guest.” He earns a whopping salary of around $50 million annually, with his income accumulating over his working years. In December 2021, Letterman bashed Donald Trump during the first Biden-Era Kennedy Center Honors.