David Letterman – $400 Million

While speaking of someone who has been around as David Letterman has, his $400-million fortune shouldn’t be surprising to anyone! After all, he got to host the Late Night with David Letterman show for just over three decades, before concluding it in 2015. Even though his show’s finished, that doesn’t mean that he’s retired.

David has since started the show called My Next Guest Needs No Introduction, which is about to begin its third season. He’s been married to Regina Lasko since 2009, even though they’ve been dating since the ‘80s. They live together on a 108-acre estate in North Salem.