Sean “Diddy” Combs, the renowned music mogul, has been the subject of gossip for years due to his notorious parties. However, following his arrest on September 16, authorities unveiled disturbing details about his alleged “freak offs” – multi-day sex parties fueled by drugs and alcohol.
The indictment accuses Diddy of forcing male and female sex workers to engage in acts that he recorded while subjecting victims to physical, emotional, and verbal abuse.Diddy has pleaded not guilty to charges of sex trafficking, racketeering, and prostitution.
Ironically, in a 1999 interview with ‘Entertainment Tonight,’ Diddy predicted that his wild parties might lead to trouble, stating, “They’re going to probably be arresting me, doing all types of crazy things just because we want to have a good time.” It remains unclear how much Hollywood insiders knew about the darker side of Diddy’s “freak offs.”
Several Hollywood celebrities have shared their experiences and opinions about Diddy’s parties over the years.
Ashton Kutcher and Sean ‘Diddy’ Combs formed an unexpected friendship while working for MTV in the early 2000s.
‘Punk’d’ former host recalled their times during a 2019 appearance on ‘Hot Ones.’ He said that their ‘bizarre’ relationship began after Diddy told him he was off-limits for any pranks.
When asked to share a memorable Diddy party story, he said that Diddy’s parties triggered a weird memory lane but refused to disclose further details.
On the 2018 ‘The Late Late Show’ Kutcher provided more insight into their friendship, he praised Diddy for his hosting skills, saying, “If you are a single man, there’s probably no greater human being in the world to hang out with.”
They even co-hosted Diddy’s 2009 white party to raise awareness for Malaria No More.
During a 2014 episode of ‘Keeping Up With the Kardashians’ Khloé Kardashian also talked about the wild nature of Diddy’s parties.
Good American founder said she was with Diddy, Quincy Combs, Justin Bieber, and French Montana and that “half the people were butt-naked” at the party.
Although Khloé shared a few details, she quickly stopped her sister Kourtney from asking more questions.
Ellen DeGeneres frequently interviewed Sean “Diddy” Combs on her daytime talk show, and in 2018, she revealed that they had occasionally partied together.
During one interview, after Combs arrived late to a taping, DeGeneres jokingly asked if he planned to be late to an upcoming party she was hosting.
“Yes, I am — no,” the “Act Bad” rapper admitted. “You know I have to arrive fashionably late.”
However, DeGeneres begged Combs not to arrive “too late,” adding, “Cause, you know, once you get there the party really starts.”
Combs told DeGeneres, “I got you. I promise you I’m not gonna let you down on this big one, for real.”
Actress Jenny Mollen revealed that she almost attended one of Diddy’s infamous ‘freak offs’ after his 2024 arrest.
She recalled being 19 years old in San Diego when a man approached her, saying, “My boss wants to meet you.” Mollen, dressed in jeans and a T-shirt, joked that she wasn’t giving off ‘sex vibes’ but was still invited to Diddy’s hotel room, which she declined.
“Guys, would I have been in a freak-off?” she asked, before bursting out laughing. “Would I have been captured in his room […] and would there be footage of me to this day in sort of a crazy exploitative freak off?”
Usher, who lived with Diddy in the 90s as a teenager shared more uncomfortable and unsettling insights of Diddy’s lifestyle.
In a 2004 Rolling Stone interview ‘My Boo’ singer said that Diddy’s house was filled with women.
“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,” he said.
Over a decade later during an interview with Howard Stern, he claimed that there were “very curious things taking place” at Diddy’s home.
When asked if he’d let his children stay with Diddy, Usher responded, “Hell, no!”
50 Cent has been one of Combs’ biggest critics even before news of his alleged abuse went public.
50 Cent has always been vocal about his discomfort with Diddy’s parties. In a 2024 interview with the Hollywood Reporter, 50 Cent explained how he steered clear of Diddy’s social life, recalling an odd moment when Diddy invited him to go shopping.
He described that shopping experience as “the weirdest s—t in the world” and said he wasn’t comfortable with Diddy’s “weird energy.”
Though they collaborated early in their careers, 50 Cent maintained that their relationship was purely professional.
He also said that other celebrities may be silent about Diddy’s actions because “They don’t know what’s on tape or what’s not on tape.”
In January 2024, comedian Katt Williams predicted Diddy’s downfall after Cassandra “Cassie” Ventura filed a lawsuit against him for rape and abuse.
On the “Club Shay Shay” podcast, Williams revealed he had repeatedly declined invitations to Diddy’s parties, even turning down $50 million to protect his integrity.
Ray J, a longtime friend of Diddy, said he had been to some of Diddy’s parties and found the accusations against him surprising, as he never witnessed anything like that.
Similarly, Kendra Wilkinson, who attended Diddy’s parties in her younger years, shared in a 2024 interview that while the parties weren’t family-friendly, she never saw anything inappropriate or harmful.
She acknowledged others may have had different experiences but said, “Nothing bad ever happened to me.”
“Sex is sex, in my opinion,” she added.