DAVID LETTERMAN – $400 MILLION

David Letterman left a mark in Hollywood as one of the best comedians there is and a former late-night talk show host. Despite retiring from his hosting job on the Late Show in 2015, the 73-year-old star still has a net worth of $400 million. In the past, David can earn $50 million a year without a sweat through licensing and syndication fees, but those years are gone.

His last episode on the Late Show on May 20, 2015, was watched by the many. It was a grand and star-studded affair that showed the degree of his impact in the industry and was watched by 13.76 million viewers. Letterman kept a low profile for most of his retirement, devoting his attention and money to causes and charities he cared about. Dave used his bundle to become a real estate mogul. In addition, he co-owns Rahal Letterman Racing, an Indy Racing league team.