Conan O’Brien: Correspondents’ dinner crowd ‘think they’re the coolest people in the world’

Former White House Correspondents’ Association (WHCA) dinner entertainer Conan O’Brien says the audience at the black-tie event is far from a comedian’s typical crowd, and they “think they’re the coolest people in the world.”

“That is not a normal crowd,” O’Brien said of Correspondents’ dinner revelers, while he appeared on a new episode of Michelle Obama and Craig Robinson’s “IMO” podcast, released Wednesday.

“They’re thinking a lot about their own world. And you need to be funny, but you can’t act like you know too much, because then they’ll resent you for that, or think you don’t belong,” the former late-night TV host explained.

O’Brien served as the headliner at the 2013 WHCA dinner.

The comic opened up about the process of attempting to entertain the journalists, lawmakers and celebrity guests that typically attend the Washington gala.

“Everything is this incredible long period of preparation to gauge what’s going to work in that room that doesn’t go too far this way, doesn’t go too far that way,” O’Brien, 62, said.

President Trump, who bucked tradition and boycotted the dinner throughout his first term, announced this week that he planned on attending the April 25 gala.

“Will be fun!” Trump wrote in a social media post.

In his conversation with the former first lady, O’Brien recounted a conversation he had with former President Obama about the event, which has earned the nickname “Nerd Prom” over the years. 

“I’ve talked to your husband about this,” he told Obama.

“They make you follow the leader of the free world,” O’Brien said, referring to commanders in chief who traditionally deliver roast-like remarks at the dinner before the night’s entertainer takes the stage.

“He goes first,” O’Brien said, “And kills it.”

“Then he would finish and like drop the mic, crowd going crazy,” O’Brien continued of following Obama.

“And a voice would go, ‘Ladies and gentleman, Conan O’Brien,'” the comedian continued, muffling his name while imitating the announcer.

“You see people like, ‘What? Who would go now?’ So you got to wade through that a little bit. But it’s all calculating for what’s the assignment,” O’Brien, who’s poised to return as host of the Academy Awards this month, said.

Likening the Correspondents’ dinner to the Oscars, O’Brien said, “Now I’m going to speak to a bunch of A-list people who don’t really like to give it up for anybody. But it’s all just a calculation. You got to calculate and then have fun.”

O’Brien, who hosted his TV show, “Conan,” from 2010 to 2021, said he’s friends with today’s field of late-night comics. 

Asked by Obama if he felt that “comedy is more fraught these days,” O’Brien replied, “I think they’re all very talented. They’re really good people and they’re in a tough situation because your job is to go out and talk about the news every day.”

“I was never strictly a comedian that lives off the news. I usually tried to find things that were silly and funny outside of the news, but we also had to do the news,” he said.

“Things are so divisive right now,” O’Brien said of comedy in the Trump era, without mentioning the president by name.

“I think it’s got to be just a really tough task and I do have empathy for people who are trying to figure out what’s funny in this,” he said, “because I know just as a citizen, I get up in the morning and I look at what happened in the news.”

“I like to be funny, but my first instinct when I read the news is nothing here gives me joy or is making me laugh that hard,” the “Conan O’Brien Needs a Friend” podcast host told Obama.

“But if you’re doing one of those shows, how do you not talk about it?” O’Brien said.

“How do you not wear your heart on your sleeve? Maybe get mad. So it’s difficult.”

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