As arguably the most legendary radio host ever, Howard Stern went from doing revolting things to being extremely wealthy and respected. As a result of his status, Howard had many celebrity interactions, even though one celebrity held a grudge against him for years and one of his interviews “hurt” a notable star. One famous person that Howard interacted with was the music superstar at the time, Sean “Diddy” Combs.
Even now that people like Joe Rogan are mocking Diddy, there is a lot of interest in his past relationship with Ashton Kutcher and why Cassie Ventura sued him. Despite how interested people still are in the rapper, most observers don’t know that Diddy once made Howard feel awful.
How Sean “Diddy” Combs Made Howard Stern Feel Like He Was A Joke
At one time, it seemed clear that just about every celebrity wanted to be associated with Sean “Diddy” Combs. Easily one of the most powerful people in music at that time, Diddy also branched out in several other ways, including as an actor.
As of 2025, however, it seems very clear that there aren’t any celebrities who want to have anything to do with Diddy. In fact, there are a number of celebrities who’ve tried to distance themselves from the rapper.
Interestingly enough, Howard Stern has spoken out about an experience he once had with Diddy. During an episode of “The Howard Stern Show,” Howard revealed how Diddy once made him feel horrible in a fascinating way.
In April 2024, someone uploaded a clip from “The Howard Stern Show” to their YouTube channel. That clip featured Howard talking about attending one of Diddy’s parties during a conversation with his co-host Robin Quivers.
Howard Stern’s Origin, According to Famous Birthdays | |
|---|---|
Where Was Howard Stern Born? | New York City, New York |
When Was Howard Stern Born? | January 12th, 1954 |
How Old Is Howard Stern As Of January 2025? | 71 Years Old |
During that conversation, Howard was talking about his history with Diddy when Robin brought up the radio host attending one of the rapper’s parties. In response, Howard agreed he did and then stated that it was an awful experience. “I just remember it was kind of a disaster.” According to a different TheThings article, Howard explained that the experience was a disaster because Diddy’s party made him feel worthless.
It ended up being very unimpressive for me because I was treated like an a******.
According to what Howard explained, Diddy made him feel awful because he was treated like a nobody.
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According to Howard, the Diddy party he attended was broken up into two sections. The most famous and beautiful people were allowed inside the house where the main party was. On the other hand, there were people outside the house who weren’t considered good enough to go inside for whatever reason.
According to an October 2020 Screen Rant article, Howard Stern is such a big deal that Sirius XM signed him to a 5-year deal that could have been worth $100 million. With that in mind, it certainly seems like Howard would be on the A-list wherever he goes.
Unfortunately for him, according to the TheThings article, Howard explained that he wasn’t allowed to go inside.
I was out with the shlubs. Only annoying people.
According to TheThings’ article, Howard stated that he was rejected when he tried to go inside the house. “They go, ‘You can’t walk inside.'”
Howard Stern stating that he was rejected from going inside one of Diddy’s party made a mark on other celebrities. During a clip of the “2 Bears, 1 Cave” podcast that can be heard on YouTube, Bert Kreischer spoke about how Howard was treated at Diddy’s party with astonishment. “Howard Stern was saying that they had an outside party and an inside party. The inside party was for celebrities, and the outside party was for celebrities that he didn’t want to show up and weren’t celebrities enough to go inside, and he wouldn’t let them inside. So they’re like, ‘I wanna go in the house.’ And they were like, ‘No.’ And it’s Howard f****** Stern.”
The audio of the radio show host talking that can be heard on YouTube featured the only positive thing Howard said about attending Diddy’s party. “It was kinda cool too because he had girls running around in bathing suits by the pool.”
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Unfortunately, TheThings’ article reveals that Howard went on to complain that he and his wife didn’t even have access to a bathroom while at the party. As a result, Howard stated that he did what he had to do.
“I had to pee so bad, and we’re in the car, and I said to the guy driving, ‘I gotta pee so f****** bad’ and my wife, or girlfriend at the time said, ‘I do too…’ I just peed on their lawn. I had no choice. I peed on their lawn. I tried to do it in a spot that wouldn’t look too bad when it turned brown. And I think Beth had to pull her pants down and pee. I’m not sure.”
Considering that Howard said attending Diddy’s party made him feel so bad, that begs an obvious question. Why did he go? The YouTube video featured Howard saying he couldn’t remember why he went to Diddy’s party.
“I don’t even know what my thought process was in going, but I’m sure it was like, ‘Hey. It might be kind of fun to talk about on the air, and and I think I don’t know if at that point he was with J. Lo or some other famous person. But it was like ‘I’m sure there’ll be a lot of famous people there, and I’ll hobnob, and it’ll be cool, and there’ll be a lot of food, and it might be fun.”
However, as the YouTube video continued, Howard suggested that he might have gone to Diddy’s party to impress his current wife, Beth Ostrosky. “I was kinda just seeing Beth, and maybe I wanted to impress her that I knew Diddy.”
Howard Stern Once Suggested What He Imagined Happened Inside Of Sean “Diddy” Combs’ Parties
According to what Howard Stern said about when he attended a Diddy party, he never got to see what really went on. With that in mind, it is fascinating to learn what Howard thought likely went on at Diddy’s parties.
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In August 2016, Howard spoke to Usher about his time living with Sean “Diddy” Combs when he was in his early teens.
After all the allegations about Diddy surfaced, Usher and Howard’s discussion went viral.
At that time, most people paid attention to what Usher said about living with Diddy. However, a YouTube clip of the interview revealed what Howard thought would go on at Diddy’s parties.
Puffy’s place was, like, just filled with chicks and orgies, like, nonstop. Right?
With that quote in mind, it is interesting that Howard took his current wife to a Diddy party when they had only begun dating.
Howard Stern
- Birthname
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Howard Allan Stern
- Birthdate
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January 12, 1954
- Birthplace
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Jackson Heights, Queens, New York City, New York, USA
- Height
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6′ 5″
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@HowardStern
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@sternshow
- Profession
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Radio Personality
- Net worth
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$650,000,000
- Source of Wealth
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Broadcasting, endorsement deals
- Nationality
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American
