“I’ve been to Puffy’s house”: Dave Chappelle reveals Diddy’s bizarre question at a party, jokes missed “my big chance to f*ck Cassie”

Dave Chappelle’s surprise Netflix special, The Unstoppable, sees the 52-year-old comedian discussing censorship in the US, including the suspension of Jimmy Kimmel. He also took shots at Bill Maher. The six-time Emmy winner mentioned Charlie Kirk’s assassination while highlighting the freedom of speech in the country. 

The Blue Streak star admitted visiting Sean “Diddy” Combs’ residence during his special, as he remarked: 

“I’m going to tell you something else I haven’t said… but this is true. In LA one night… I shouldn’t even tell— f*** it. I’ve been to Puffy’s house.” 

Before dropping the significant revelation, Chappelle recounted one instance he seemingly defended and said: 

“I was on stage not long ago in the States and n****s got mad ‘cause I said, ‘Well, you know, maybe Puff will get off.’ And I said, ‘I hope so.’ And the crowd was like, ‘Boo.’”

Chappelle claimed that he doesn’t think Diddy is right, but remembered how the hip-hop mogul once saved his life. Chapelle added:

“I was on stage not long ago in the States and people got mad because I said maybe Puff will get off. It’s not that I think Puff is right, but when I got attacked in LA at the Hollywood Bowl, people forget Puff was the guy that tackled my attacker. He saved my life.”

He added that it’s hard for him to be mad at Diddy after he saved his life. Chappelle joked:

“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.”

Dave Chappelle added: 

“Years later, when I heard about that baby oil, I was like, what did those dudes slip on? A thousand bottles of baby oil. That’s a lot. It’s not illegal. It’s gross, but it’s not a crime.”

The comedian then revealed that he had visited Diddy’s residence before he went on trial. 

Dave Chappelle jokes about his visit to Diddy’s house and their interaction in The Unstoppable 

The You've Got Mail actor claimed to have visited Sean Combs’ residence once in his latest Netflix special. Dave Chappelle claimed he did not encounter anything that was mentioned in Diddy’s trial, as he recounted:

“I walked through that n****’s living room, house was clean, traction on the floor, nothing slippery, walked right through. Perfectly normal evening.” 

Chappelle claimed that their interaction was pretty normal, but added that he found one specific “f***ed up” in hindsight. The comedian said: 

“We was on his back patio, and we was drinking and laughing, and talking, and then Puff starts swirling his drink like this, and he goes, ‘So, Dave.’ He goes, ‘What are you into?’ You know me, I didn’t— I was like, ‘I don’t know n****, books, video games, um…’”

Chappelle joked:

“I didn’t know that was my big chance to f*** Cassie. God bless her.” 

Chappelle asserted that he is not making fun of Cassie Ventura and acknowledged that what she went through was terrible. Dave Chappelle spoke about the case and trial before moving on to the other bit.

Dave Chappelle also addressed the Riyadh Comedy Festival backlash

Dave Chappelle talks about a night at Diddys 🤔 pic.twitter.com/mEEjVbji9C

— mrredpillz jokaqarmy (@JOKAQARMY1) December 21, 2025

The Chappelle's Show host was criticized for participating in a Saudi Arabian government-sponsored comedy festival earlier this year. He said: 

“Recently, in the news, I’ve been getting a lot of grief, again… Because I did a comedy festival in Saudi Arabia.” 

The crowd cheered as soon as Chappelle addressed the controversy surrounding the Saudi comedy festival. The comedian pointed out that all the applause is from the Black people and asserted that “America’s whites” are furious, as he claimed:

“Boy, I gotta tell you something, I’ve never not felt guilty about something. Like, I’ve never felt […] I don’t feel guilty at all.”

He attacked Bill Maher over his commentary and said:

“You know, and Bill Maher, the famous comedian, I’ve known Bill since I was, like, 18, 19 years old, and I’ve never said this publicly, but f*** that guy.” 

He asserted that he’s tired of Maher’s commentary. Chappelle called out the critics for their hypocrisy over his Saudi Arabia festival performance. The comedian also hit back at the naysayers, claiming that it was “easier to talk in Saudi Arabia” than it was for him in the USA. Dave Chapelle remarked:

“Two years ago, I almost got canceled right here in the United States for transgender jokes. But I gotta tell you something. Transgender jokes went over very well in Saudi Arabia.” 

Dave Chapelle does not agree with Ezra Klein's lionization of Charlie Kirk pic.twitter.com/oJl077PQmy

— Sam Haselby (@samhaselby) December 20, 2025

Chappelle also spoke about Charlie Kirk’s assassination in his Netflix special. He addressed the comparisons made by some people who called Kirk “this generation’s Martin Luther King Jr.” Chappelle acknowledged the similarities in their assassinations but claimed that it was an exaggeration to compare the late TPUSA founder with Dr. King. 

He described Kirk as an internet personality who had to say certain things to get traction, which was not the case with Martin Luther King Jr.