Diddy’s White Party Photos Resurface: Leonardo DiCaprio and Jennifer Lopez Among the Guests

With news of Sean "Diddy" Combs’s "Freak Off" events making headlines after his arrest in New York over allegations of abuse and coercion to "fulfill his sexual desires," renewed interest has emerged around his past events. While his parties were known for their wild reputation, people are now taking a closer look at both the gatherings and the guest lists. Photos from his iconic annual White Party have resurfaced, and honestly, the content of some is enough to raise eyebrows.

Diddy's White Parties were held from 1998 to 2009 and attracted major Hollywood names, including Leonardo DiCaprio and Jennifer Lopez. From topless women splashing around in the pool to groups of men posing together on the couch for photo ops, here’s a peek at what a few of Diddy’s White Parties actually looked like.

With the flood of allegations following Cassie's 2023 lawsuit against Diddy, photos from his infamous White Parties are circulating online, and people are looking at them closer than ever. In this 1999 shot, Diddy is seen standing above a crowd of guests at his Hamptons home, which he reportedly sold in 2020 for $4.7 million.

Diddy's events often attracted A-list celebrities like Sarah Jessica Parker, Aaliyah, Jennifer Lopez, and Ashton Kutcher. One photo, which we've opted not to include for obvious reasons, shows champagne being poured on two topless women embracing each other. Diddy can be spotted in the background, although it's unclear if he's the one holding the champagne bottle.

Diddy's 1999 White Party was packed with celebrities, to say the least. From Regis Philbin to Vera Wang, it seems all the biggest names were on his guest list.

You can't tell from the photo above, but Leonardo DiCaprio is also in the picture. He was sipping his champagne while the others around him posed for a photo.

The Titanic star appeared to be having a great time at the iconic White Party in 1999, although there's no evidence that the celebrities present were involved in any of the alleged incidents Diddy has been accused of partaking in. However, the same cannot be said for other events.

A drug dealer who allegedly sold cocaine to the disgraced rapper during one of these gatherings revealed to The New York Post, "You’d see two people you would not think would be hooking up, rappers; that was what shocked me."

They added, “I won’t say names but there were rappers that I immediately lost respect for and could not take seriously ever again.” After being welcomed into Diddy's Hampton's home, the dealer says he saw “a mix of [female rappers] and hookers,” who were reportedly "already high on ketamine and GHB," per The Post.

What’s a party without stunning women dressed as angels serving champagne? Sweet Tooth star Dania Ramirez, seen in the middle, has certainly come a long way in the entertainment industry. Who would have thought she once served Champagne in angel attire at one of Diddy’s legendary White Parties?