Richard Simmons – 73

Richard Simmons has successfully made a name for himself as a fitness instructor since the ’60s. He released the Sweatin’ to the Oldies videos which mainly focus on weight loss through a very energetic approach. Simons started out his career through a gym he opened and called Slimmons. Since then, through his appearances in television and his products, he became well-known around the U.S. and getting great paychecks. However, since 2014, his appearance in public began declining and his facility had closed down without stating any reason. In April 2017, he revealed he was suffering from severe indigestion which led to his hospitalization.