The redheaded comic riffs on everyone from Donald Trump to President Obama

By Megan Johnson
Updated September 14, 2015 10:55 AM

Most people assume that Conan O’Brien and his fellow late night hosts must love having Donald Trump in the headlines every day. But according to the Conan host, having to turn Trump’s soundbites into comedy is “not great.”

“It’s so absurd,” said O’Brien, who appeared on a panel about presidential humor as part of the John F. Kennedy Library Foundation’s New Frontier Network in Boston on Saturday night. “How comedy works is, you say the setup, and it’s not supposed to make people laugh. With Trump, you say the setup, and people are laughing. And then you’re supposed to top that! I find it actually more difficult. We’ve had insane people run for president.”

The local favorite, who was raised in nearby Brookline and attended Harvard University, says that even though Trump is “very strange” and behaves “like a man that came from another planet,” there isn’t much left he could say that would make the public turn against him.

“Trump has gotten to a point where, I cannot think of something he can say right now that would lower his approval rating,” said O’Brien. “He’s broken through some crazy barrier no one’s broken through before. I like it.”

But it wasn’t just Trump that O’Brien let loose on; he also laughed at President Barack Obama‘s willingness to appear in less formal circumstances as he heads toward the end of his second term.

“I was driving in the car and had the radio on, and they said ‘tonight President Obama’s going to be on with Bear Grylls’ and it felt like, we’re getting very close to Japanese game show,” O’Brien joked. “Now he’s really loose and really relaxed, ‘I drop by Keeping Up with the Kardashians‘ tonight.’ Don’t do that, come on!”

“It does seem like at a very certain point the president is going to have come from a show where he’s naked on a dating island but then have to address the nation,” he told the crowd. “It seems very schizophrenic.”

When it comes to which POTUS really makes Conan laugh, O’Brien said the best presidential humor is the unintended kind (like Nixon’s) or the ironic and off-the-cuff type, like JFK’s.

“I like my president to see the world as an absurd, screwed-up place, and have a sense of irony about it,” said O’Brien. “Because I think that’s the best human characteristic someone can have if they’re trying to lead the free world.”