Richard Simmons, 74 – $20 Million

Richard Simmons was a very big deal back in the day when he had people sweatin’ to the oldies in a series of his best-selling exercise videos. Designed to help you get in shape in a fun way, Simmons’ videos reportedly sold a record 20 million copies.

During his early teens, Simmons weighed in at 268 pounds before getting the inspiration to lose more than 100 pounds. This led to his multi-million dollar fitness empire, making him an overnight celebrity. It is reported that his classic training videos will be available for free very soon on Fuse Sweat, a free streaming channel on VIZIO SmartCast.