David Letterman holding up his hands on The Late Show with David Letterman

David Letterman was able to accumulate lots of wealth during his run as the host of the Late Show, and that still holds true today. In fact, prior to Elon Musk purchasing Twitter, David Letterman and his team were in the mix, with an offer of their own worth billions.

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Over the course of interviewing celebs, Letterman definitely had his favorites off-camera. According to Richard Simmons, he wasn’t one of them… Simmons was a reoccurring guest on the show, who always managed to entertain the fans. However, off-camera, Simmons struggled to connect with Letterman. In truth, it wasn’t the first time Simmons struggled with a host, the same held true during his time alongside Howard Stern.

We’ll reveal what went on between Letterman and Simmons, particularly when the two would chit-chat during a commercial break.

Richard Simmons Appeared On The Late Show Several Times But Never Got To Meet David Letterman Off-Camera

via YouTube

Richard Simmons appeared on The Late Show multiple times, taking part in some hilarious interviews. There was chemistry between Letterman and Simmons. However, that didn’t hold true behind the scenes. According to Simmons, he never saw Letterman before or after the interview backstage. It was downright in front of the camera, and that was basically it.

Simmons said, “I love David. He’s more complicated than any of them, that David,” Simmons shares. “You know, I’ve never actually met him? . . . You do the show with him, and when they go to commercial, they remove you. You’re just not allowed to talk to him. Or if you are, he’s very standoffish.”

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Simmons’ experience with Letterman got a little more complicated during an incident that took place at the commercial break. According to Simmons, he made an attempt to get to know the host further outside of the show, but it wasn’t meant to be…

Richard Simmons Revealed David Letterman’s Attitude Is Completely Different On And Off Camera

Simmons himself was skeptical about returning to the Late Show, after multiple experiences of being ignored by the host. He said, “Maybe one day, when the time and everything is right. Because I do love him,” Simmons discussed about a potential return.

However, Simmons had a rough incident take place with Letterman, trying to make casual conversation during a commercial break. According to Simmons, he wanted to make an attempt to know Letterman outside of the show, but the host instantly shot it down.

“The last time I was on, we went to commercial and I was like, ‘I’d love to meet your wife!’ He was like, ‘You never will.’ And then I was like, ‘And see your son!’ And he was like, ‘You’ll never see him.’ And then we come back from the commercial and he’s all friendly with me again. You think I’m kidding, but I’m not making this up.”

RELATED – David Letterman Wanted To Skip Over To Commercial After He Almost Got Kicked In The Head By Crispin Glover

Fans might not be too surprised by Simmons’ revelation, given that Letterman had a bit of a history ‘bullying’ certain guests at times. However, on the flip side, he did favorite certain celebs. Although he didn’t visit Simmons prior to the show, he did when it came to other A-listers…

David Letterman Greets His Favorite Guests Before Shows – But He Has More Than A Few Guests That He Didn’t

david letterman and oprah
via YouTube

A particular story from behind the scenes is a classic example of a guest Letterman loves, and one he does not.

Prior to shooting an episode of The Late Show, the host went to visit Meryl Streep’s dressing room. However, upon entry, Letterman was in for a big surprise, as he found another guest going through her purse. It was another guest that appeared multiple times, filmmaker Harmony Korine.

Letterman recalls, “I went upstairs to greet Meryl Streep and welcome her to the show, and I knock on the door … and she was not in there,” he said. “And I looked around, and she was not in there, and I found Harmony going through her purse. True story. And so I said: ‘That’s it, put her things back in her bag and then get out.”

Letterman retold the story with James Franco years later, and it seems as though Korine was banned from the show following the backstage incident.

That was far from the only interview that went off the rails. Crispin Glover nearly knocked Letterman’s head off with a kick during their interview, while Paris Hilton faced uncomfortable questions from the host, like a discussion about her jail time, despite the fact that she clearly did not want to discuss the topic.

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