Inside Disgraced Diddy's Star-Studded Parties: Photos Surface From Rapper's Hamptons Bash After Depraved 'Freak-Offs' Alleged in Indictment

Sean "Diddy" Combs was once viewed as a "modern-day Gatsby" whose extravagant A-list parties were hailed as legendary. But these get-togethers emerged in a new light after the hip hop producer was slapped with a federal sex trafficking indictment detailing the depraved "freak-offs" he's been accused of orchestrating.

RadarOnline.com obtained photos from one of Diddy's star-studded soirees, showing the likes of Leonardo Dicaprio, Chevy Chase and Regis Philbin schmoozing at his swanky beachfront mansion in the Hamptons in 1999.

A photojournalist also claimed to have spotted Diddy and his ex, Jennifer Lopez, getting cozy at the bash around the time they began dating.

Between 1998 and 2009 – long before Diddy's steep fall from grace – the Bad Boy Records producer held lavish annual Labor Day "white parties" where guests were required to dress in all white or be denied entrance.

Some regulars on the guest list reportedly included members of the Kardashian family, the Hilton sisters, Jay-Z, Beyoncé, Mariah Carey, Mary J. Blige, Al Sharpton and Martha Stewart.

Paris Hilton recalled being at the first bash in 1998, telling The Hollywood Reporter 10 years later: "It was iconic and everyone was there."

But Combs, now 54, also noted he "had the craziest mix" of guests, telling Oprah Winfrey in 2006 that he brought "some of my boys from Harlem" and "relatives from down south" together with "socialites" because he "wanted to strip away everyone's image and put us all in the same color, and on the same level”.

He said of his first-ever white party: "There were 200 people sitting out here, just having a down-home cookout," adding this included "Leonardo DiCaprio, after he'd just finished Titanic".

In photos from his second white party on September 4, 1999, a smiling 24-year-old Dicaprio could be seen holding something resembling a cigarette as he lounged around with Diddy, then 29, and A Tribe Called Quest's Jarobi White. who each appeared to be holding champagne bottles. In another photo, the Titanic actor, now 49, took a sip from a glass as Diddy, with a woman in his lap, gestured toward the camera.

Photojournalist Selma Fonseca told The Sun in 2021 she was at the event, and recalled: "There were celebrities like Regis Philbin, Vera Wang and Chevy Chase in the crowd."

Snaps from the gathering showed the Vacation star, now 80, and Who Wants to Be A Millionaire host, who died at age 88 in July 2020, in white garb at the packed party.

The photojournalist also described a moment she witnessed between Diddy and J Lo, who was 30 at the time.

Fonseca recalled: "I saw him coming out of a balcony off the master bedroom suite and J Lo was with him. She made the first move.

"She put her arm on his shoulder and she kissed him and there they were, making out a little bit and then he lit a cigar and they came downstairs.

“He was holding her hand and a Cuban band was playing and they started dancing."

The pair broke up in 2001.

In subsequent years, Diddy moved the parties to other luxurious venues in places like Beverly Hills, California and Saint-Tropez, France. The opulence and notoriety surrounding the parties continued, as the media branded the host a "modern-day Gatsby".

At his 2004 party in the Hamptons, Diddy reportedly made a grand entrance, descending into the event via helicopter.

In a clip that resurfaced in the wake of the criminal charges against Combs, Ashton Kutcher joked about the wild get-togethers. When the host said: "Diddy party stories, they're our favorite genre of anecdote if you have one", Kutcher laughed and replied: "I've got a lot I can't tell".

The actor's remarks hit differently in the wake of the indictment accusing Diddy of subjecting women and male prostitutes to drug-fueled "extended sexual performances" he allegedly called "freak-offs" that sometimes lasted for days.

One commenter noted the clip of Kutcher "aged horribly", while another expressed concern about the "things he can't talk about when partying with Diddy", noting "the recent news that came out about things that went on at Diddy parties."

The three-count indictment against Combs was unsealed following his arrest this week, revealing allegations that he "planned and controlled" these "freak-offs" and "often electronically recorded them."

Prosecutors said these sessions "involved multiple commercial sex workers, and often involved a variety of narcotics such as ketamine, ecstasy and GHB, which Combs distributed to the sex workers to keep them obedient and compliant."

The indictment further alleged "when Combs didn't get his way, he was violent and subjected victims to physical, emotional and verbal abuse so that they would participate in the freak-offs" and claimed he "hit, kicked, threw objects at, and dragged victims, at times by their hair." The alleged incidents date back to at least 2008, according to prosecutors.

None of the individuals mentioned in this report, aside from Diddy, have been accused of wrongdoing in connection with the charges.

Combs is currently being held at a Brooklyn detention center while awaiting trial for alleged sex trafficking, racketeering and transportation to engage in prostitution.

The music mogul has vehemently denied the allegations against him and pleaded not guilty in court this week.

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