I heard him on the radio and was so jarred by his manic voice even without having to see his balding perm and pink unitard that I immediately googled, "Why is Richard Simmons popular". I came back with an interesting dissertation paper
http://www.iath.virginia.edu/pmc/text-only/issue.995/pop-cult.995
The paper proposed the idea that gay men and obese women occupy the same sexual space in our society. Popular society is passively disgusted by their sexuality and, therefore, they relate to and console eachother. While every other exercise show features beautiful women leading other beautiful women in a work out, the obviously homosexual Richard Simmons leads obese women on his program. Say what you want about the guy but he's clearly clever enough to profit from the combination of two of our society's taboos while staying true to himself.
This explains some odd friendship pairings many of us have seen where a gay man in designer jeans will be friends with an obese woman wearing a Winnie the Pooh sweatshirt (or some such combination). Oh well, you gotta find some happiness somewhere in this world.
