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Last week, Diddy was arrested in Manhattan after he was indicted on sex-trafficking and racketeering charges. But before the music mogul was facing multiple lawsuits accusing him of sexual abuse, he was known for throwing some of the most extravagant parties in the entertainment industry.
Throughout the early 2000s, Diddy’s annual White Party was the hottest ticket in the Hamptons. Now, with disturbing details emerging about his alleged dayslong “Freak Offs” — prosecutors claim he would provide copious amounts of drugs to female attendees and male sex workers and make them perform sex acts while he watched and masturbated — people are questioning what actually went down at Diddy’s other parties. In a resurfaced clip from his 2002 interview with Conan O’Brien, Diddy laid out his tip for a good party: “A lot of ladies drink water at parties, so if you don’t have what they need, they’re going to leave. Got to keep them there. You need locks on the doors … It’s a little kinky.”
In 2002 Sean “P. Diddy” Combs explained to Conan O’Brien his “Freakouts” – Including seducing women with liquor – Making sure bedroom doors on them were always locked while restricting air conditioning in their rooms while claiming “It depends on the way you look at it”
Creepy pic.twitter.com/4xKX2rycKR
— TaraBull (@TaraBull808) September 20, 2024
Here, what we know about Diddy’s parties over the years.
Who went to Diddy’s parties?
A better question would be, Who didn’t go to a Diddy party? Name someone who was famous in the early aughts and there’s a photo of them partying with Diddy. Leonardo DiCaprio, Sarah Jessica Parker, Martha Stewart, Jamie Foxx, Russell Simmons, Jennifer Lopez, Jay-Z, Vera Wang, Russell Brand, Chevy Chase, Kim Kardashian, Paris Hilton, LL Cool J, Aretha Franklin, Reverend Al Sharpton, and even Regis Philbin have all been photographed at a Diddy party over the years.
Photo: Jon FurnissPhoto: Dimitrios KambourisPhoto: Dimitrios Kambouris/WireImage for Bragman Nyman Cafa
What happened at Diddy’s parties?
From 1998 to 2009, Diddy threw an annual White Party, which was noteworthy not just for its strict white-only dress code but for bringing together the old-money (read: white) denizens of East Hampton and the new generation of hip-hop stars. In a 1999 interview with Entertainment Tonight, Diddy said that his parties were about “breaking down racial barriers, breaking down generation barriers.” His example at the time was that the billionaire businessman Ron Perelman could be seen talking to Jay-Z at one of his parties (this was before Jay-Z had become a business tycoon). In 2001, the Independent quoted Diddy saying, “Have I read The Great Gatsby? I am the Great Gatsby!”
Diddy parties certainly had a flair for the dramatic. At his 2004 White Party, which doubled as a kickoff event for his get-out-the-vote organization Citizen Change, Diddy arrived via helicopter straight from the curtain call of A Raisin in the Sun on Broadway. In his arms was an original copy of the Declaration of Independence, on loan from the prolific television producer Norman Lear.
Photo: Johnny Nunez/WireImage
The parties would start in the daytime and go long into the night. In the early hours, it appears there was more of a family-friendly vibe: There are photos of Diddy and his then-partner, Kim Porter, holding their twin babies at a White Party in 2007. At the same party, Diddy posed with his young sons. At a certain point, it would transition to an adults-only affair. In a video obtained by the Daily Mail, Diddy stands on a balcony to address the crowd at one of his White Parties. “We fed you all. We gave you drinks. Now it’s time to enjoy life,” he said before addressing the children at the event. “Kids have an hour left [because] this thing turns into something that when you get older, this is something y’all gonna want to come to … So let’s just start to get our groove on. Put the kids away. It’s all good.”
Photo: Mat Szwajkos/Getty ImagesPhoto: Bryan Bedder/2007 Getty Images
Over the years, people have alluded to what sort of things happened at Diddy’s parties. In addition to a lot of famous people in attendance, it seems as though there were usually also naked people and drugs. Photos published by the Daily Mail show Diddy pouring Champagne onto topless women. In another photo, two topless women straddle a man in the pool while pouring Champagne into his mouth. Other photos show partygoers like Lopez lounging on what appears to be a large bed. At another 2004 party, this one in Miami, Diddy was photographed eating a chocolate-covered strawberry off a naked woman being used as a serving tray. According to the Daily Mail, which published the photos, several A-listers were in attendance at this party, including Diana Ross, Will Smith, Bruce Willis, and Owen Wilson.
In a June YouTube video, content creator Tom Swoope told a story about attending one of Diddy’s White Parties in the early aughts. He claimed that the party was “tiered off” and that there was the “general admission” area and more private VIP areas as you made your way through the house. In the video, he claimed that there were lots of drugs (namely ecstasy and cocaine) and people engaging in sexual activity.
The New York Post interviewed a drug dealer who claimed to have sold Diddy cocaine at his Hamptons home during a party. The dealer said that Diddy opened the door wearing nothing but a robe and led him back to a bedroom — again, it seems like most of the illicit activity happened away from any main area. “Weird shit was starting to happen. Celebrity guys fucking each other. There were back bedrooms, and it was like the inner sanctum,” he explained to the Post. The dealer also claimed there were sex workers at the party and that many attendees were using ketamine and GHB.
In the TMZ documentary The Downfall of Diddy: The Indictment, former publicity director for Bad Boy Entertainment LaJoyce Brookshire was asked if she ever felt that Diddy’s parties could take a turn for the nefarious.
“My spidey senses were always on high alert. And I know that there’s no safety after a certain hour when you’ve got drinks flowing and people behind your back doing drugs in bathrooms, and two or three people walking out of a bathroom together … so could there potentially be? Absolutely. Did I see it? No. I never stayed at the party late enough to see.”
What have people said about Diddy parties?
People did not usually go on the record about Diddy’s parties, but over the years we’ve gotten a few quotes about what they were like. In his 2019 episode of Hot Ones, Ashton Kutcher — who co-hosted the White Party in 2009 to raise awareness for a malaria-fighting charity — was asked if he had any Diddy-party stories he could share. “I’ve got a lot I can’t tell,” he told host Sean Evans before putting on a show of going through his mental rolodex. “Can’t tell that one, either. I’m actually cycling through them.”
Photo: Michael Tran/FilmMagic
In July, 50 Cent told The Hollywood Reporter that he had avoided Diddy’s social circle. “I’ve been very vocal about not going to Puffy parties and doing shit like that,” he said. “I’ve been staying out of that shit for years. It’s just an uncomfortable energy connected to it.”
Khloé Kardashian talked about partying with Diddy in a 2014 episode of Keeping Up With the Kardashians. The reality star said that Justin Bieber (then 20) and French Montana were also there and that “half the people there were butt naked.”
Usher, a protégé of Diddy’s, lived with the mogul in New York for a year in 1994, when he was 13 and Diddy was 24. In a 2004 Rolling Stone interview, Usher said, “Puff introduced me to a totally different set of shit — sex, specifically … There was always girls around. 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.” However, he changed his tune in a 2016 interview with Howard Stern, when he denied that Diddy’s home was “filled with chicks and orgy-ing,” as Stern had said, but did admit that it was a “curious” environment. When asked by Stern if he would let his own children have a similar experience, Usher said emphatically, “Hell no.”
Are the parties connected to Diddy’s alleged “Freak Offs”?
It seems that while there might have been sexual activity at Diddy’s parties, the Freak Offs that are mentioned in both his federal indictment and the complaint filed against him by his ex-girlfriend Casandra “Cassie” Ventura were their own, separate thing.
In the indictment, prosecutors describe Freak Offs as “elaborate and produced sex performances that Combs arranged, directed, masturbated during, and often electronically recorded.” Ventura’s complaint explained that Freak Offs usually took place in luxury hotels, not Diddy’s home. They allegedly could last for days at a time, and participants would require IV fluids afterward owing to physical exertion and drug use.
When asked by the Daily Mail about DiCaprio’s attendance at Diddy’s parties, a source close to the actor stressed that the parties were not Freak Offs. “[DiCaprio] attended a few of [Diddy’s] parties back in the early 2000s — but literally everyone did … They were not Freak Offs,” the source explained. “They were big house parties.”
As for Diddy, he has repeatedly denied the allegations against him and pleaded not guilty to charges of sex trafficking and racketeering. We have reached out to representatives for Diddy and will update this post when we hear back.
This post has been updated.
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