Sean “Diddy” Combs can’t stop, won’t stop making headlines.
During the surprise Netflix special Dave Chappelle: The Unstoppable, Chappelle told Diddy jokes, discussed politics, and mocked MAGA comparisons between MLK and slain conservative commentator Charlie Kirk.
The comedian defended his recent stand-up performance in Saudi Arabia, after letting it slip that he was paid $6 million. Walking across the stage, smoking, and looking physically unwell, Chappelle said his jokes have gotten less pushback from the Saudis than from the transgender community in the U.S.
He also called out Israel for killing “240 journalists in the last three months,” and detailed a private moment with Diddy.
Related: 50 Cent Teases ‘140 Hours’ of Unseen Diddy Documentary Footage
Chappelle told the audience he visited the music mogul’s Los Angeles mansion, but insisted nothing unseemly happened — no baby oil, no escorts, no red light rooms.
“I’ve been to Puffy’s house,” Chappelle 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, traction on the floor, nothing slippery. You walk right through. Perfectly normal evening.”
But the story took a cringeworthy turn when Chappelle recalled a conversation he had with Combs.
“Puff started swirling his drink like this and he goes, ‘So Dave, what are you into?’” Chappelle said. “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–k Cassie.”
The audience wasn’t sure how to react and responded with nervous laughter to Chappelle’s musings about Diddy’s ex-girlfriend Casandra “Cassie” Ventura.
The singer and actress testified against the Bad Boy Records founder during his criminal trial and alleged she was repeatedly physically assaulted, raped, and trafficked by the mogul.
Ventura filed a civil lawsuit against Combs in November 2023, alleging he punched, beat, kicked and stomped on her. The complaint said she needed intense therapy after moving on. She is now married with three young children.
Diddy settled the lawsuit the next day, but denied the allegations.
In May 2024, CNN aired leaked surveillance footage, showing Combs kicking and dragging Cassie down a hallway in a Los Angeles hotel in 2016.
Diddy posted and later deleted an apology video on Instagram, saying his behavior in the footage was “inexcusable,” and he had gotten counseling after the incident.
During the trial, Cassie said she was trying to flee after a “freak-off” sex session with the mogul and a male escort when the footage was recorded. She told the court Combs settled her lawsuit for $20 million and the hotel paid her another $10 million.
A hotel security staffer testified that Combs paid him $100,000 cash to stop the footage from “getting out.”
Another hotel security guard, who is a now an LAPD officer, also took the stand. He said he responded to Diddy’s room right after the altercation, and declined a payoff. “He had a sack of money and he threw it at me and said, ‘Don’t tell anyone,’” Israel Florez testified.
What Diddy didn’t know, Florez secretly recorded a copy of the video with his phone and held onto it for years.
Combs was convicted for prostitution-related Mann Act violations, and is now serving 50 months in federal prison.
Dave Chappelle: The Unstoppable began streaming on Netflix Dec. 19. The special was recorded in Washington, D.C.
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