Dave Chappelle is back turning real-life headlines into comedy, this time digging into a past moment with Diddy that feels different in today’s climate.
In his latest Netflix special, Dave Chappelle The Unstoppable, the comedy legend shared a story that didn’t hit the same way until years later.
Chappelle kicked things off by describing a visit to Diddy’s Los Angeles home, making it clear nothing felt off at the time.
“I’ve been to Puffy’s house,” Chappelle told the crowd. “No, I didn’t see none of the stuff they said in that trial. I walked to that n*gga’s living room. House is clean, traction on the floor, nothing slippery. You walk right through. Perfectly normal evening.”
But the story took a turn when he recalled a conversation on Diddy’s back patio that, in hindsight, carried a different meaning.
“Puff started swirling his drink like this and he goes, ‘So Dave, what are you into?’” Chappelle said. “You know me, I was like, ‘I don’t know, n*gga. Books, video games.’ I didn’t know that was my big chance to fuck Cassie.”
The line landed with uneasy laughter, shaped by the serious allegations and legal scrutiny surrounding Diddy and his former partner, Cassie Ventura. Chappelle was careful to clarify that he wasn’t making light of Ventura’s experience.
He also addressed the viral hotel footage showing Diddy assaulting Ventura, which resurfaced after federal charges were made public. Chappelle reminded fans that Diddy wasn’t criminally prosecuted for that incident and noted Ventura’s civil lawsuit, filed in November 2023, was settled privately.
Although the settlement details weren’t disclosed, Chappelle acknowledged the rumors floating in the industry before shifting to a respectful note.
“Cassie is a gangster,” he said. “She did something I wouldn’t wish on my worst enemy. She had to testify about her sex life. That’s tough.”
