While Richard Simmons is fondly remembered for his Sweatin’ to the Oldies aerobics videos and The Richard Simmons Show, he also leaves behind an iconic late-night legacy. The fitness instructor and actor—who died on Saturday, July 13 at age 76—made numerous appearances on late-night talk shows over the years.
Although he appeared on many programs, Simmons’ guest stints on Late Show with David Letterman were especially memorable. He and David Letterman would bicker, pull pranks on each other, and get up to all kinds of shenanigans.
Just a month before his death, Simmons took to social media to reminisce about his many Late Show appearances. In a lengthy Facebook post, he revealed that he’d never actually watched Letterman’s show prior to guesting on it. “To be honest, I never saw his show,” he wrote. “I don’t stay up late at night.”
Simmons and Letterman had quite the dynamic. While the host pulled plenty of pranks on him, the teasing certainly wasn’t one-sided. “For some reason, I enjoyed aggravating David,” Simmons admitted in his post.
Simmons arrived at the studio for his inaugural Late Show appearance carrying a “bronze-colored metal Halliburton briefcase,” the contents of which he refused to reveal.
“They said David doesn’t like surprises. I said to myself, ‘Who cares?’” Simmons wrote. “They advised me not to bring it on the set. Well, you know what I did? I walked on the set and put it right on [Letterman’s] desk.”
The contents of the mysterious briefcase turned out to be $10,000, laid out in the form of $100 bills. Simmons proposed that Letterman appear in his next Sweatin’ to the Oldies video, an offer the host promptly refused. “He began to chuckle and told me to put the money away,” Simmons wrote.
Of course, that was just the beginning of the fitness guru’s long affair with the Late Show. “On my next visit, they cut two holes in my tank top and fitted me with a halter that was attached to a thick piece of rope,” Simmons wrote. “Two stagehands lifted me up so the audience couldn’t see me. Then David came out and said, ‘Where is my next guest?’ And like Tinkerbell, I came flying down.”
One of the most iconic, and most infamous, moments between the duo occurred in a November 2000 episode when Simmons came onto the stage dressed as a giant turkey. “I was covered with bright yellow feathers and a head piece that was yellow and orange,” he recalled. “David looked at me and said, ‘Take off your head.’ And I looked at him and said, ‘Take off your head.’”
The antics didn’t stop there. Simmons ran around the stage in costume, putting on a grand show for the crowd. Then, when he grabbed Letterman’s shoulder and seemingly attempted to give him a kiss or a hug, the host hosed him with a fire extinguisher.
“He reached behind his desk and took out a fire extinguisher… then sprayed me from head to toe,” Simmons wrote. “I had an asthma attack and the ambulance came and got me.”
After the fire extinguisher incident, Simmons didn’t appear on the Late Show for six years. When he returned in 2006, Letterman welcomed him back with open arms… and yet another prank. This time, an exploding vegetable steamer sent Simmons running for the hills.
In the end, despite all the pranks and banter, there was also clearly a lot of love between Letterman and Simmons.
“I have to admit, I think I was one of David’s favorite guests,” Simmons wrote. “The show told me that my appearances got very good ratings.”
Indeed, just hours after the news of Simmons’ passing was announced, Letterman’s YouTube channel posted a fond remembrance of the frequent guest.
