David Letterman
With a net worth of $400 million, this retired late-night talk show host earned a salary of $50 million for his work. Letterman presented on the series for 33 years between 1982, when Late Night with David Letterman debuted on NBC, and 2015 when Late Show with David Letterman wrapped on CBS. Letterman surpassed his friend and mentor Johnny Carson as the longest-serving late-night talk show host in American TV history.
Also, a TV and film producer, Letterman's company produced a number of shows and prime-time comedies, such as Everybody Loves Raymond. Conan O'Brien, Letterman's successor on The Late Show, cites Letterman as one of his biggest influences—along with Jimmy Fallon, Jimmy Kimmel, John Oliver, and Seth Meyers. Letterman now hosts My Next Guest Needs No Introduction with David Letterman on Netflix.