There Was Never a Funnier Howard Stern Guest Than Richard Simmons

‘One of the greatest all-time nuts I’ve ever encountered’
There Was Never a Funnier Howard Stern Guest Than Richard Simmons

Heaven gained a Weight Saint this weekend when Richard Simmons, 76, passed away from undisclosed causes. Simmons was a well-known fitness champion thanks to infomercials and a series of best-selling videotapes, but he truly gained fame thanks to his goofy appearances on talk and comedy shows. Simmons was a Late Night With David Letterman Hall of FamerWhose Line Is It Anyway’s funniest improviser and a slam-dunk go-to guest on Howard Stern’s radio show for decades. 

Stern devoted a section of his memoir Private Parts to “one of the greatest all-time nuts I’ve ever encountered.” That’s thanks to bits like Simmons showing up during one of Robin Quivers’ news segments dressed “in full nurse regalia, with fake nails, earrings, a beehive hairdo, the works. He then spent the rest of the show denying he was dressed like that. He did the same thing a few months later when he showed up on Ash Wednesday dressed like a nun.”

After years of staying out of the public spotlight, Simmons had taken to Twitter in recent months to reminisce about his life, including his Stern appearances. The shock jock shared one of those memories last month. 

“Richard one time was coming on the show, I didn’t know he was coming in,” Stern said. “He dressed up as what he would call a biker or a real man. He put on a wig and a mustache, and he put on a muscle shirt. He came in and started roughing me up and started telling was going to kick my ass, and I was scared shitless. I didn’t know it was Richard Simmons.”

While Simmons’ outrageous behavior made him a fan favorite among Stern listeners, “he was a bit hard on me,” Simmons tweeted in February. Stern would admit it — a lot of the weight loss guru’s appearances involved frat-boy insinuations about his sexuality. Stern wasn’t exactly subtle either. “Hey Richard, what do you like to eat?” he asked during one early guest spot. “You like hot dogs? Sausage? Carrots? Zucchinis? Bratwurst? How about a giant cucumber for dinner?”

In fact, Simmons left his last Stern appearance in tears after Stern refused to relent. For years, Simmons would laugh and deflect rather than answer Stern’s questions, but not this time. Referencing the show when the leather-clad Simmons showed up “dressed like a man,” Stern told Quivers that Simmons "embraces both sexes. You’re sometimes very womanly, you appeal to both sexes.” That was finally enough for Simmons, who left the studio in tears.

Simmons and Stern had a friendly relationship outside the show, including dinners at Stern’s home and Simmons coming up with the name for Stern’s daughter Ashley. Earlier this year, producer Gary Dell’Abate revealed that he’d been in contact with Simmons as a friend, not as a potential guest. “He did some really nice things for my family,” said Dell’Abate, aka Baba Booey. “He visited my brother in the hospital. He bought my mother a dress for my wedding. He was just super nice to us.” 

“I don’t want people to be sad about my brother,” wrote Richard’s brother Lenny Simmons after the unexpected news. “I want them to remember him for the genuine joy and love he brought to people’s lives. He truly cared about people. He called, wrote and emailed thousands of people throughout his career to offer help. So don’t be sad. Celebrate his life.”

Or as Stern put it in Private Parts, “He’s a warm and generous person, and I love him.”

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