Dave Chappelle says he thinks he once had a chance to hook up with Diddy and Cassie, recalling an awkward conversation with the Bad Boy mogul during his new Netflix special, The Unstoppable... He joked that Diddy once asked him what he's "into," which he now believes carried a very different meaning than he realized at the time.
“I’ve been to Puffy’s house,” Chappelle admitted onstage, as caught by Complex. “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.”
From there, Chappelle explained that he was sitting on the back patio when Diddy hit him with the question. “Puff started swirling his drink like this and he goes, ‘So Dave, what are you into?’” Chappelle recalled. “You know me, I was like, ‘I don’t know, n***a. Books, video games.’ I didn’t know that was my big chance to f*ck Cassie.”
Before moving off the topic, Chappelle praised Cassie for testifying against Diddy during his criminal trial, earlier this year. “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.”
Diddy is currently residing behind bars for two counts of transportation to engage in prostitution. He is serving a 50-month sentence for the conviction.
Dave Chappelle's "The Unstoppable..."
It wasn't the only point where Dave Chappelle mentioned Diddy during the standup special. Recalling an incident in 2022, in which someone rushed the stage to attack him at the Hollywood Bowl in Los Angeles, he revealed that Diddy intervened to help him.
“I was on stage not long ago in the States and people got mad because I said maybe Puff will get off,” Chappelle said. “It’s not that I think Puff is right, but when I got attacked in L.A. at the Hollywood Bowl, people forget Puff was the guy that tackled my attacker. He saved my life.”
He added: “I had security that night, but they just wasn’t ready. They ran out, all them slipped and fell. Puffy got my attacker and tackled him.”
