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And then, he will burst into a chorus of Captain & Tennille in that inimitable tenor — “Do that to me one more time. ” — just to remind us that, after all, he is Richard Simmons. ” Today is one of the 200 days each year Richard Simmons is on the road, giving motivational speeches, posing for fan pictures or promoting whatever new product he has out. ) Richard Simmons travels everywhere dressed like Richard Simmons.