David Letterman confronted Howard Stern about his friendship with Paramount Pictures’ Brad Grey in an unearthed interview.

Howard Stern‘s relationship with David Letterman dates back to the earliest days of the legendary radio show host’s profitable career. Stern was a frequent guest on The Late Show, contributing to its success and inadvertently adding to David Letterman’s outrageous net worth. Letterman returned the favor on multiple occasions by being interviewed on SiriusXM’s The Howard Stern Show. But the pair were never more electric than when on the late-night CBS series.

On one particular occasion, Letterman, who was known for causing guests to almost walk out mid-interview, slammed one of Stern’s friends. Stern was noticeably shocked by Letterman’s brutal comments and this was something fans picked up on. This article will reveal what Letterman said about Stern’s friend, the former CEO of Paramount Pictures Brad Grey, and why he hated him so much. Following that, we will reveal the truth about Stern’s relationship with Grey.

Howard Stern Defended His Friendship With Brad Grey After David Letterman Called Him “Evil”

During Howard Stern’s November 22, 2013 appearance on The Late Show with David Letterman, the pair reminded viewers of their excellent repartee. However, things took a turn mid-way through the late-night interview when Letterman’s feud with Jay Leno was mentioned. In fact, Stern was visibly upset when Letterman admitted to taking a call with Leno. This is because Stern was a staunch ally of Letterman’s during his ongoing late-night feud with fellow comedian, Leno. Stern may have been even angrier about the situation than Letterman himself was.

The conversation led to the topic of forgiveness and celebrity friendship. This is when Letterman absolutely slammed someone that Stern spent time with — former Paramount Pictures CEO Brad Grey.

During their conversation, David Letterman and Howard Stern bonded over their shared disinterest in socializing and how they ultimately should have been better friends because of it. Letterman also grilled Stern on what kind of experience his guests have when they come over for dinner with him and his wife, Beth. Letterman was blown away by how many celebrity friends Stern has made, particularly after a career of bashing them. Stern’s friendship with Letterman’s producer Rob Burnett was mentioned, as was his extremely close relationship with Jimmy Kimmel. And then Paramount Pictures CEO Brad Grey’s name was brought up and the interview’s energy shifted dramatically.

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Jimmy Kimmel and Molly McNearney

Jimmy Fallon and Nancy Juvonen

Jon Bon Jovi and Dorthea Hurley

Robert and Susan Downey Jr.

Brooke Shields

Courteney Cox

Jennifer Aniston

Steve Martin

Robin Quivers

Billy Joel and Alexis Roderick

Jerry and Jessica Seinfeld

Mary McCormack

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While Stern explained his friendship with the late great comedian Don Rickles, he brought up Brad Grey’s name which caused Letterman to pretend to choke. As Stern explained that he was invited by the late CEO of Paramount Pictures home, Letterman continued to cough, changing the energy of the interview up dramatically. But Stern continued, stating that Rickles said something ‘disparaging’ —

“About Brad Grey?” A hopeful David Letterman asked.

“No, about me,” Stern replied, trying to continue on past Letterman’s noticeably disgusted reaction. But Letterman clearly had a point to make about Grey, so he continued:

“You see, now I’m a little worried because now we’re talking about Brad Grey. I was with you with Jimmy Kimmel and Don Rickles. These are working guys. These are blue-collar guys. These are guys getting it done. And now we go up into the level of evil, controlling, idiots.”

Stern was noticeably taken aback by Letterman’s comments, causing the audience to verbally react.

“Oh, Wow!” Stern exclaimed. “He’s an idiot?”

“Yeah,” Letterman responded.

“Brad is?”

“Yeah.”

“Wow… I don’t have that experience with him. Wow. What happened to you? ‘Brad Grey is an idiot’? Why don’t you say that about Jay Leno!?”

Letterman claimed that Grey represented a certain type of person that one wouldn’t want to be associated with. Stern, ever the showman, decided to turn things around on Letterman by continuously bashing his attempt at making peace with his former late-night rival. This included Stern telling Letterman that he liked his passion but that it was misplaced on Brad Grey and instead should be focused on ripping up Jay Leno.

The Late Show host continued by calling Stern “a sellout” for making friends with someone he used to work for. Stern claimed that he hasn’t “railed against everybody”, but mentioned a few bosses that he hated, including former NBS boss Grant Tinker. But Letterman praised Tinker for being a good person.

“Oh, that’s your buddy?” Stern asked. “What happened to you, Mr. Sellout?

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“You’re having drinks with Brad Grey!”

“And I will continue to!”

“Oh my god!”

“I made my movie with Paramount Pictures,” Stern said of his 1997 blockbuster, Private Parts. “I like the guy… what did he do to you?”

“It’s not him. It’s showbusiness weasels. You and I are in business to stamp out showbusiness weasels.”

“Your boss, Less Moonves, is he a showbusiness weasel?” Stern asked, alluding to his fiery feud with the then-CBS CEO before the allegations that brought his career down.

“Well… he’s..” Letterman stumbled. “If he wants to be, he can be a showbusiness weasel.”

“What did Brad Grey do to you!?” Stern asked one more time.

“Nothing. I never met the guy,’ Letterman admitted.

“And you hate him!?” He’s a lovely guy.”

David Letterman continued by claiming that Howard Stern had sold out to the people he used to bash. But Stern defended himself by claiming that “nobody” wants him to have any friends. And one powerful person in his life does not make him “a sellout”.

Howard Stern’s Relationship With Former Paramount Pictures CEO Brad Grey

Little is known about the extent of Howard Stern’s relationship with former Paramount Pictures CEO Brad Grey. However, we do know that the pair got to know each other in the mid-1990s when Stern was making his semi-autobiographical film, Private Parts, with the movie studio. We also know that the two spent time together socially. Stern revealed more about their relationship after Grey passed away on May 14th, 2017 following a secret battle with cancer.

“The guy was a huge success, a real nice guy, and I’m sad to see that he’s gone,” Howard Stern said on the Monday show following Grey’s death. Stern claimed he first met Grey when he cameoed on The Larry Sanders Show with Garry Shandling. At the time, Grey was the executive producer as well as Shandling’s manager.

“I ended up being friends with both of them.”

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Stern also claimed that Brad Grey was likely “tickled” by his argument on The Late Show with David Letterman.

“I think Brad was really actually tickled by it … because Brad was a behind-the-scenes kind of guy.”