Jackie Mason – 87
Best known as a stand-up comedian and actor, Masons sketches typically involved conversial topics such as politics and religion. Mason ranked number 63 on the 100 greatest stand-up comedians in history, as listed by Comedy Central. A man who did not fear judgment, he wasn’t bothered by other’s perception of his demeanor and sketches. Controversy breeds publicity, and his career has gained him $9 million in net worth. He still pursues his acts today at 86 years old. Mason married his manager, Jyll Rosenfeld, in 1991, and they are still together until today.