Partying with Sean Combs: Old stories gain new life

In 2005, when Sean Combs — also known as Diddy and Puff Daddy — hosted the MTV Video Music Awards, the network advertised the broadcast with a playful star-studded spoof called “Diddy Parties,” in which the events he hosted were referred to as “hedonistic romps.”

It’s one of many examples that illustrate how the powerful music mogul’s reputation for hard-partying was an accepted part of the pop culture discourse. But since Combs’ recent arrest on charges of racketeering conspiracy and sex trafficking, the lifestyle at the center of the criminal case has taken on a different light.

Those who attended his events — whether his glitzy, A-list “white parties” or the “freak-offs” described in the indictment against him — have largely refrained from discussing their experiences in recent weeks. That hasn’t always been the case. In years past, celebrities have openly talked about his public-facing bashes and his general party habits.

Here is some of what Combs and other stars have said about his party orbit.

In his words

In a 1999 interview with Entertainment Tonight, in response to an interviewer who said, “Your parties are the hottest ticket around,” Combs said, “They won’t even give me a permit for the parties no more.”

“They don’t want me to throw the parties no more, but we ain’t going to stop, we going to keep on having fun, bringing people together from all walks of life,” he added. “You’re going to hear about my parties, they’re going to be shutting them down, they going to probably be arresting me, doing all types of crazy things just because we want to have a good time. Whenever you bring up a different element into people’s environment, things that broaden people’s horizons, people get intimidated.”

In 2002, Combs joined late-night host Conan O’Brien, who asked what the ingredients were for “an amazing, killer party.” Combs offered a lengthy response, starting with: “This is what you need to do. Women. Beautiful women, of course. Beautiful men for the ladies, of course.”

“You have to give the ladies what they need, too, you have to take care of your women,” he added.

“You need alcohols, you need some water,” Combs continued. “I don’t know if guys have noticed this, but a lot of ladies drink water at parties, so if you don’t have what they need, they’re going to leave. Gotta keep them there. Need locks on the doors.”

“This is sounding kind of dangerous now,” O’Brien said.

“It’s a little kinky,” Combs said, adding: “You need a lot of heat. Don’t have no air-conditioning. Heat affects the alcohol. Everybody also gets a little more comfortable and loose, builds up a nice little sweat.”

“That just sounds disgusting,” O’Brien quipped.

A teenage Justin Bieber posted a YouTube video in 2009 titled Justin Bieber’s 48 Hrs With Diddy!!

In it, Bieber appears to be on Combs’ property, where they look at one of Combs’ cars.

“Where we’re hanging out and what we’re doing, we can’t really disclose, but it’s definitely a 15-year-old’s dream,” Combs says to the camera. “I have been given custody of him. He’s signed to Usher. I had legal guardianship of Usher when he did his first album. I did Usher’s first album. I don’t have legal guardianship of him, but for the next 48 hours, he’s with me. And we going to go full, buck-full crazy.”

“Forty-eight hours,” Bieber said in the video. “Let’s go, um, let’s just go get some girls. Let’s go hang with some girls.”

“Man after my heart,” Combs said. “That’s what I’m talking about.”

In a video captured by an attendee at one of Combs’ parties (the year it was filmed is unclear) and posted last week by The Daily Mail, he addresses the crowd from a balcony.

“To all the kids, the kids have like an hour left, so get extra comfortable, kids, because after that, you all got to go,” Combs said in the video. “It’s a wrap for you all. Because this thing turns into something that when you all get older, y’all are going to want to come to. OK? So, you know, let’s just start to get our groove on a little bit and in an hour, we put the kids away. It’s all good.”

What celebrities have said

In a 2004 interview with Rolling Stone, R&B singer Usher Raymond discussed living with Combs in New York for a year in the early 1990s, when Raymond was 13 years old and building his fledgling career. He was sent there by music executive Antonio Reid, known as LA Reid, to create an album with Combs, who was then in his early 20s.

Raymond told Rolling Stone that Combs had introduced him to a different set of experiences — “sex, specifically,” he said. “There was always girls around,” he added. “You’d open a door and see somebody doing it, or several people in a room having an orgy. You never knew what was going to happen.”

On an episode of The Howard Stern Show in 2016, Raymond was again asked about that year living with Combs.

“In the ’90s! Do you understand what that’s like?” Raymond said.

When Stern asked if Combs’ house “was like just filled with chicks and orgy-ing like nonstop,” Raymond said: “Nah, not really, but hey, it was curious. I got a chance to see some things.”

“I went there to see the lifestyle, and I saw it,” he added. “But I don’t know if I could indulge and understand what I was even looking at. It was pretty wild. It was crazy.”

“Would you ever send your kid to Puffy camp?” Stern asked.

“Hell no,” Raymond said.

In 2009, rapper Xzibit said he once accompanied Combs to a club after a New Year’s Eve party in Miami. Xzibit mentioned seeing nude people engaging in sexual activity at the club.

“We take off,” Xzibit said. “We leave the club directly. I didn’t say peace to nobody. It was suspect.”

Khloe Kardashian discussed partying with Combs in Las Vegas during a 2014 episode of Keeping Up With the Kardashians.

Her sister Kourtney guessed which celebrity friends were in attendance, naming Bieber and French Montana, among others. “So far, so good,” Kardashian replied, confirming the guesses.

Later in the episode, Kardashian described the party in more detail. “I haven’t been to bed yet. I got on a plane at 5:30 a.m. for this party,” she shared, adding, “I think half the people there were butt-naked.”

In a 2018 interview on The Late Show With Stephen Colbert, actor Jamie Foxx discussed partying with Combs.

“Puff showed up with the SUVs, the FBI,” Foxx said about a particular gathering. “Puff was always sort of dangerous. So, he had all kinds of people following him.”

Ashton Kutcher briefly discussed Combs in a 2019 episode of Hot Ones, before deciding not to veer too deeply into the topic.

Asked by the host, Sean Evans, if he had any “Diddy party stories,” Kutcher said, “I’ve got a lot I can’t tell.”

“Can’t tell that one either,” Kutcher said, mentioning that he was “actually cycling through them.”

“Diddy party stories, man, that was some weird memory lane thing,” he added later in the episode, shaking his head. “Ugh.”

In a 2021 post to his Instagram Story, rapper Fabolous, discussing how he often ducked out of celebrity-filled events, said he left a party while Combs was still going at 7 a.m.

“I told Diddy I was going to the bathroom and slid once,” he said. Combs, Fabolous added, “was still turnt!”