"Oh my God. Carl Winslow? And I wasn’t invited": Dave Chappelle trolls Diddy over freak-off parties on SNL

Comic Dave Chappelle appeared on Saturday Night Live’s first episode of 2025 on Sunday, January 18. The controversial funny man made quips on several topics, including President-elect Donald Trump, the Los Angeles wildfires, and Sean “Diddy” Combs’ much-discussed ‘freak-off’ parties. While discussing the now-infamous rapper, Chappelle spoke about not being invited to the events and Diddy’s baby oil bottle collection.

While talking about the embattled hip-hop mogul, Dave Chappelle said in his 17-minute monologue:

“I’ve been in a lot of trouble in my day but this guy Puffy, oh buddy, this guy is in an enormous amount of trouble; I don’t think I’ve ever seen anything like this.”

Diddy is now behind bars, awaiting his May 5 trial date as he faces s*x trafficking, pr*stitution, and racketeering conspiracy charges.

The veteran comic, who has been to SNL four times, then discussed Family Matters star Reginald VelJohnson, who took on the role of Carl Winslow in the series. VelJohnson was accused of attending Diddy’s events and also getting intimate with Diddy. As per Page Six, VelJohnson has since denied getting intimate with Combs and said, “I don’t know that man.” Speaking about the same, Chappelle said on the SNL stage:

“I saw something on the internet—probably not true, but it said Puff was in the back with Carl Winslow. And I thought, ‘Oh my God. Carl Winslow? And I wasn’t invited? It’s worse than I thought.”

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“I’m ugly”: Dave Chappelle jokes about not being invited to Diddy’s ‘freak off’ parties because of being unattractive

While being joined by musical guest GloRilla, Dave Chappelle continued to discuss Diddy’s alleged ‘freak off’ parties and why he supposedly never attended them. The comic said:

“They’d be like, ‘Well how were all these people you know at the freak-off and you were the only one who wasn’t at the freak-off?’ And I thought about it for a minute and I said, ‘Oh my god- I’m ugly.’ That was a tough way to find it out. Can you imagine if you were me reading the newspaper and found out everyone in Hollywood had an orgy behind your back? None of y’all called me?”

Dave Chappelle also discussed Diddy’s Miami and Los Angeles mansion raids that took place in March, where the FBI seized over 1000 bottles of baby oil and lubricant as evidence. Chappelle remarked:

“I’m 51 and I don’t think I’ve ever finished a bottle of baby oil in my life. Clearly Puff is committed to the lifestyle. A thousand bottles? Thank God they caught him before those fires- can you imagine the mushroom cloud over his house?”

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Sean Combs is currently in the Metropolitan Detention Center awaiting his trial after pleading not guilty.

As per the indictment against Combs, the Bad Boy Records mogul allegedly- “hit, kicked, threw objects at and dragged victims, at times, by their hair” at his s*x parties. The indictment also alleged that Diddy recorded himself subjecting his alleged victims to “physical, emotional and verbal abuse to cause the victims to engage in freak-offs.”

As per News.com, if convicted, Combs could spend the rest of his life in prison.