The lawsuit filed Monday is seeking unspecified damages as well as an apology and retraction for stories published in June 2016 and March 2017 in the Enquirer and its website, RadarOnline.
The lawsuit against American Media, Inc., states the stories rely on a man who has tried to blackmail the former fitness guru for years, and included a 2013 photo of Simmons dressed in drag.
WATCH: Missing Richard Simmons’ Podcast
It states Simmons often dressed as a woman as part of his public persona.
Simmons retreated from public life in 2014, sparking rampant speculation about his health and wellbeing.
The Enquirer wrote in a statement that it is standing by its reporting on Simmons.