Richard Simmons

Richard Simmons was a memorable recurring guest on The Howard Stern Show from the late '80s into the 2000s. Known for his over-the-top energy, emotional openness, and wild sense of humor, Simmons often added a unique, unpredictable dynamic to the show. Howard and the team enjoyed playfully teasing him, particularly about his flamboyant personality and iconic workout videos, which led to many laugh-out-loud interactions.

The chemistry between Simmons and Stern created a mix of light-hearted ribbing and genuine friendship. Richard’s sensitivity was often on display, as he sometimes cried or got overly emotional during interviews, which Stern would both poke fun at and appreciate. His catchphrases, unique laugh, and expressions like "I love you, Howard!" became fan favorites. Their interactions highlighted Richard’s joyful personality but also explored the complex layers of his life and struggles, especially as Simmons started to withdraw from the public eye around 2014.