‘I’ve Been In Trouble In My Day’ But ‘This Guy Puffy, Oh Buddy’ Dave Chappelle Unloaded On Diddy During His SNL Opening Monologue

Dave Chappelle laughs during his opening monologue on SNL.
(Image credit: NBC & SNL)

Dave Chappelle returned to Studio 8H for his fourth time hosting Saturday Night Live, and as per usual, he did not hold back in his opening monologue. During an over seventeen minute masterclass that was hilarious, thoughtful and touching, the comedian talked about the Los Angeles fires, Donald Trump returning to office, Jimmy Carter, Haitian immigrants and Diddy. Oh buddy, did he go in on Diddy.

Chappelle devoted about five minutes of his monologue to a full analysis of the Diddy situation and how much trouble he’s currently in. He said he’s had his share of controversies and been in trouble before, but he’s never seen anything like this Diddy situation. You can read a portion of his quote below…

I’ve been in trouble in my day. Well, I’ve been in a lot of trouble in my day, but man, let me tell you something, 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. They got this guy in a RICO case by himself.

In typical Chappelle fashion, however, he took an abrupt 180 and hilariously said his initial reaction was that he must be considered ugly not to be invited to these freak off parties. He said he had no idea what was going on, and to find out everyone in Hollywood was having orgies behind his back “hurts.” He called it a “tough way” to find out no one considers him attractive. You can read more of his quote below…

A lot of my friends ask me, they say, ‘Dave, did you know anything about those freak off parties?’ I’m like, ‘Nah, man. I don’t know anything about the freak off.’ And they all look at me like (skeptical face). They’re like, ‘How come all these people you know is at the freak off and you’re the only one that wasn’t at the freak off?’ I thought about it for a minute and said, ‘Oh my God, I’m ugly.’ That’s a tough way to find that 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 ya’ll called me. Well, it really hurts.

Chappelle later focused on the fact that Reginald VelJohnson, who played Carl Winslow in Family Matters, was accused of being at the parties and not him. Veljohnson, who also played a key role in Die Hard, has denied he was involved, and Chappelle said it was probably just an internet rumor, but regardless, he just can’t get over living in a world where VelJohnson might have gotten invited to an orgy and not him. He admitted that made him reconsider whether it was actually a matter of handsomeness and instead might be because his face has “snitch energy.”

You can watch his hilarious monologue below. The Diddy stuff is roughly between 9:00 and 14:00 and includes a hilarious bit near the end where he talks about how he’s all for giving people a chance to grow and learn from their mistakes as they get older, but if you’re 55 and have 1,000 bottles of baby oil, you probably “can’t stop, won’t stop.”

Dave Chappelle Stand-Up Monologue 2025 - SNL - YouTube Dave Chappelle Stand-Up Monologue 2025 - SNL - YouTube
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It definitely wasn’t only comedy in Chappelle’s monologue though. The comedian paid a very touching tribune to Jimmy Carter, where he talked about how people disagree about the former President’s quality as an actual President but said he started crying when he saw a picture of him walking through Palestine with almost no security back in the day, surrounded by thousands of people. He complimented him for being a good man that did the best he could before closing with some thoughts on incoming President Trump.

Chappelle was very measured with his words and with trying to bring people together; so, I’ll let his quote speak for itself…

Donald Trump, I know you watch the show. Man, remember, whether people voted for you or not, they’re all counting on you. Whether they like you or not, they’re all counting on you. The whole world is counting on you. I mean this when I say this, ‘Good luck.’ Please, do better next time. Please, all of us, do better next time. Do not forget your humanity, and please have empathy for displaced people, whether they’re in the Palisades or Palestine.

Saturday Night Live will return next week with a brand new episode that’ll be led by the next upcoming host Timothée Chalamet. This’ll be the third time the Complete Unknown star has hosted, and if it’s anything like the last times, it should be fantastic.

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