Dave Chappelle recounts bizarre night at Diddy’s house and admits he had no idea what the mogul was really asking him

Dave Chappelle is making jokes about the recent Diddy controversies in his new Netflix special, Dave Chappelle: The Unstoppable…. He talked about a strange night he spent at Diddy’s Los Angeles home years ago. The comedian said he had no clue about the drama that was reportedly happening behind the scenes back then.

According to Complex, Chappelle told the audience he visited Diddy’s house but didn’t see any of the things that came out during the recent investigations and trials. He said the home looked normal. “I’ve been to Puffy’s house,” Chappelle said on stage. “No, I didn’t see none of the stuff they said in that trial. I walked to that n****’s living room. House is clean, traction on the floor, nothing slippery. You walk right through. Perfectly normal evening.”

The night got awkward when Chappelle and Diddy were hanging out on the back patio. Diddy started swirling his drink and asked Chappelle a loaded question: “So Dave, what are you into?” Chappelle thought Diddy meant hobbies or interests, so he answered innocently: “You know me, I was like, ‘I don’t know, n***a. Books, video games.'”

Chappelle realized too late what Diddy actually meant

Chappelle later understood that the question had a much darker meaning, given the allegations that came out later. He joked about his mistake: “I didn’t know that was my big chance to f*** Cassie.” However, he quickly made sure the audience knew he wasn’t making fun of Cassie Ventura or her serious experiences.

Chappelle also talked about the hotel surveillance video that recently went viral. The footage showed Diddy assaulting Ventura, and it came back into the spotlight after federal charges against Diddy became public. The comedian pointed out that Diddy was never criminally tried for that specific incident. In other celebrity controversy news, Grimes recently revealed the silly thing Elon Musk just did to her on the platform he owns, and she’s not impressed.

Ventura filed a civil lawsuit in November 2023, which was settled very quickly. The exact settlement amount was never made public, but Chappelle joked about industry rumors regarding how much money was paid.

Despite the jokes, Chappelle showed deep respect for Ventura. He called her a “gangster” and recognized how difficult it must have been for her to take legal action. He said she had to do something extremely hard: “She had to testify about her sex life. That’s tough.” Speaking of artists speaking out, SZA just called the White House’s behavior “peak dark” after they used her hit single in a shocking immigration enforcement video.

Chappelle made it clear that even though he was making jokes, some topics need to be treated with respect and seriousness.