David Letterman – $47 million
David Letterman is a true “pull yourself up by your bootstraps” kind of guy. After his attempt at an NBC morning show failed, he had to start once more at the bottom. In 1982, he switched to CBS and christened Late Night with David Letterman. The show was soon an enormous success. A recent retiree, Letterman is still raking in millions from owning his own show and production company. Reruns of The Late Late Show with Craig Ferguson, The King of Queens, and Everybody Loves Raymond keep Letterman swimming in the moolah. This guy is the definition of determination.