What They Saw! Leonardo DiCaprio, Khloe Kardashian and More Who Partied With Sean ‘Diddy’ Combs

Zipped Lips

Ashton Kutcher briefly shared what a party hosted by Diddy is like during a 2019 appearance on Hot Ones.

“I’ve got a lot I can’t tell,” the That 70s Show actor told host Sean Evans. “Can’t tell that one either – I’m actually cycling through them. Diddy party stories, man, that was some weird memory lane thing.”

The clip of his interview resurfaced following Diddy’s September 2024 arrest, leading fans to question Ashton’s friendship with him.

“Ashton is seriously concerned about getting dragged into his ugly mess,” a source exclusively told In Touch on October 1, 2024. “People are outraged, and they want answers.”

Puff Mummy

After Kelly Osbourne (with Diddy’s mom, Janice) gushed about how “manicured” the 2003 party host was, her mom, Sharon, joked that he’d make a great son-in-law, adding, “I bet he’s got a nice old willy and all! I’ll bet it’s smooth. I bet it’s oiled.”

There to Party

Tommy Lee, Mariah Carey, Star Jones and Reverend Run dressed in white for the 2007 do — a hot invite at the time. Former protégé Aubrey O’Day, who’s accused the rapper of grooming her, predicts, “There are way more victims. There is a lot more crazy s–t. As this unfolds, more people will be heard.”

King of the World

Titanic star Leonardo DiCaprio enjoyed a 1998 White Party. The indictment against Diddy alleges that the music mogul taped the kinky goings-on and “used the sensitive, embarrassing and incriminating recordings … to ensure the continued obedience and silence of the victims.”

Caught In the Act

In a 2014 ep of Keeping Up With the Kardashians, Khloé recalled seeing Justin Bieber, then 20, at a Diddy affair. “ I think half the people there were butt naked,” she told sister Kourtney Kardashian on the show. “You would have loved it!” The rapper has pleaded not guilty to sex trafficking.