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Dave Chappelle hosted Saturday Night Live over the weekend and delivered a 17-minute-long monologue that touched on a variety of topics, including Sean ‘Diddy’ Combs. Chappelle famously mocked Combs on Chappelle’s Show two decades ago.
During his monologue, Dave Chappelle began talking about Diddy and marveled at how much trouble the disgraced rapper and producer is, joking that’e he’s been put in a RICO case “by himself” (RICO stands for Racketeer Influenced and Corrupt Organizations).
“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… They’ve got this guy in a RICO case by himself!” Chappelle joked during his 17-minute-long monologue.
Chappelle then transitioned into Diddy’s now infamous “freak off” parties at which many of the crimes he’s accused of committing occurred. Chappelle claimed to not know anything about the parties because he wasn’t invited for being too ugly.
“A lot of my friends asked me, ‘Dave, did you know anything about those ‘freak-off’ parties?’ I’d be like, ‘Nah, man.’ I didn’t know anything about [the] freak-offs.”
Chappelle then imitated the doubt-filled face his friends would make when he would claim to not know anything about the party before launching into the next set-up and punchline.
“Can you imagine reading a newspaper and finding out everyone in Hollywood had an orgy behind your back? None of y’all called me. That really hurts. 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!”
😂😂Dave Chapelle on the Diddy party’s. Chapelle still the 🐐 pic.twitter.com/lkehx1dMKi
— Brent (@HJhughes79) January 19, 2025
On his generational sketch comedy series Chappelle’s Show that aired on Comedy Central 20 years ago, Chappelle famously mocked Diddy with a skit making fun of his reality TV show Making The Bands. In the skits, Chappelle portrayed Diddy as eccentric and abusive to his subordinates.
Diddy, who faces a minimum of 15 years and a maximum of life in prison if convicted of the federal charges he faces, is set to begin his trial in May.
You can watch Chappelle’s full monologue from this weekend’s episode of Saturday Night Live below.