Dave Chappelle took a no-holds-barred approach during his 17-minute monologue on Saturday Night Live, poking fun at the troubled rapper and music mogul Sean “Diddy” Combs. Chappelle didn’t shy away from addressing the ongoing legal issues surrounding Diddy, including the federal charges he’s facing, to which Diddy has pleaded not guilty. Chappelle joked about Diddy’s alleged “freak-off” parties, saying he was too “ugly” to have been invited to them, making light of the situation while taking aim at the rapper’s legal woes.
“I’ve been in trouble in my day, but let me tell you, this guy, Puffy… this guy Puffy is in an enormous amount of trouble; I don’t think I’ve ever seen anything like this,” Chappelle remarked, referencing Diddy’s serious charges. The comedian then recalled a conversation with a friend who asked about the alleged parties, to which Chappelle responded with mock surprise, saying he had no idea that “everyone in Hollywood” had been secretly partying without him.
He humorously added, “None of y’all called me. That really hurts,” highlighting how out of the loop he felt in this bizarre situation. Chappelle also made a playful reference to actor Reginald VelJohnson’s rumored connection to Diddy, which had been denied by VelJohnson, who famously portrayed Carl Winslow on the classic sitcom Family Matters. Chappelle quipped, “And I thought, ‘Oh my God. Carl Winslow? And I wasn’t invited? It’s worse than I thought!'”
Diddy, who is currently incarcerated in a Brooklyn prison, faces multiple charges including sex trafficking, racketeering, and prostitution. His attorneys have argued that the alleged “freak-off” videos actually serve as part of his defense, claiming they show the encounters with the complainants were consensual. The legal filing states, “There are no secret cameras, no orgies, no other celebrities involved, no underground tunnels, no minors, and not so much as a hint of coercion or violence.” Despite the serious nature of the charges, Chappelle’s humor was a lighthearted approach to an otherwise dark situation.