David Letterman ~ $400 Million

David Letterman hosted the Late Night with David Letterman and The Late Show for years. Earning $50 million a year in syndication fees and licensing was an easy thing to do for David Letterman in previous years, but that value has slightly decreased. You could say that Letterman is on par with other iconic television hosts such as Johnny Carson and Jack Paar.

He became popular for being a sharp and frank interviewer, with many fans finding his honesty unusually pleasant. His career started as early as 1982, releasing a total of 6,080 episodes between his two shows. He was ranked by TV Guide as one of the Best TV Stars of all Time. He retired in 2015 with a net worth of $400 million and has several real estate investments. 13.76 million people watched his last show, and it was announced that Stephen Colbert would be the successor of the show.