Dave Chappelle turned headlines about Sean “Diddy” Combs and Cassie Ventura into comedy fuel during his new Netflix special Dave Chappelle: The Unstoppable… telling a crowd he once hung out at Combs’ Los Angeles home and had no clue what was really going on behind the scenes.
“I’ve been to Puffy’s house,” he said. “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… perfectly normal evening.”
Chappelle told the story with a mix of straightforward honesty and ridiculous hindsight, setting up a punchline about missed opportunity.
“He goes, ‘So Dave, what are you into?’ You know me, I was like, ‘I don’t know, n####, books, video games.’ I didn’t know that was my big chance to f### Cassie.”
Chappelle shifted gears to the fallout from the viral hotel video showing Combs attacking Ventur, the clip that resurfaced after federal charges hit.
“God bless her. I’m not making light of her, the way she went through was terrible,” he said.
He reminded the audience that Combs wasn’t on trial for that assault, and that Ventura’s civil lawsuit, filed in November 2023, was settled almost immediately.
The payout amount was never disclosed, though Chappelle referenced the industry rumor mill:
“He paid her $35 million, is what I heard. Which doesn’t make it right, but I mean, come on, n####. I do know n##### that have fought Floyd Mayweather for less money than that. And them n##### had to fight for 36 minutes,” Chappelle said.
Then came the gut punch: “Cassie is a gangster. She did something that I wouldn’t wish on my worst enemy. She had to testify about her sex life. Boy, that’s tough.”