‘Hollywood had an orgy behind my back’: Dave Chappelle mocks Diddy’s ‘freak offs’ with hilarious SNL monologue

'Hollywood had an orgy behind my back': Dave Chappelle mocks Diddy's 'freak offs' with hilarious SNL monologue

Dave Chappelle brought his trademark wit to the Saturday Night Live stage and took aim at the explosive allegations surrounding music mogul Sean “Diddy” Combs. With his trademark mix of humor and biting commentary, Chappelle explored the absurdity of the situation during his 17-minute monologue.
“This guy, Puffy, buddy. This guy is in a tremendous amount of trouble. I’ve never seen anything like it,” Chappelle said, referring to the federal charges Combs faces, including sex trafficking and orchestrating the bizarre, elaborate “Freak” . Offs.” “They got this guy in a RICO case by himself,” he added.
The comedian delved into rumors of Combs’ infamous parties and joked about his alleged suspension. “A lot of my friends asked me, ‘Dave, did you know about the free golf parties?’ I’d be like, nah, man, I didn’t know anything about free golf.”
Chappelle went on to weave a fictional tale of spotting Carl Winslow, the beloved father figure from Family Matters, at one of these parties. “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!’ ” His hyperbolic outrage sent the audience into fits of laughter.
The jokes didn’t stop there. Chappelle talked about the bizarre details of the allegations, particularly the reported discovery of over 1,000 bottles of baby oil in Combs’ home. “I’m 51 and I don’t think I’ve ever finished a bottle of baby oil in my life,” he joked. “Clearly Puff is committed to the lifestyle. A thousand bottles? Thank God they caught him before they caught fire – can you imagine the mushroom cloud over his house?”
During his 17-minute monologue on SNL, Chappelle touched on several hot topics, including the LA fires, Luigi Mangione, aka, the Healthcare CEO Killer, and the recent election. He also offered his thoughts on the upcoming inauguration and delivered a sharp message to incoming President Donald Trump.

Legal problems arise for Diddy

While Chappelle kept the tone light, the background of his monologue remains deeply serious. Sean Combs, 55, is currently in jail after his arrest in September, awaiting trial on sex trafficking charges. Prosecutors allege that Combs orchestrated elaborate “Freak Offs” in which participants were allegedly drugged and forced into sexual acts.
In court, Combs’ lawyers have vehemently denied the allegations, calling the case “sexist and puritanical.” In a letter to a federal judge in Manhattan, they argued that nine recordings submitted as evidence depict consensual sexual encounters. “Any fair-minded viewer of the videos would quickly conclude that the prosecution of Mr. Combs is both sexist and puritanical,” they wrote, arguing that the government is demonizing non-conforming sexual activities.
The defense claims the footage, provided by an alleged victim, shows no signs of coercion, violence or manipulation. “In all six of these encounters, Victim-1 is not only consenting; she is obviously happy, dominant and completely in control,” they stated, challenging the prosecution’s narrative.

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Dave Chappelle Stand-Up Monologue 2025 – SNL