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Inside every conspiracy theorist is a person who desperately wants to be thought of as smart and kind, and is angry they’re not seen that way. That, and also someone who’s bored.


That’s the read, at least, from Jordan Klepper, the comedian who’s spent the past three months hosting the Alex Jones-style parody “The Opposition” on Comedy Central, working hard to get into the heads of all the conspiracy theorists—including President Donald Trump himself—who’ve latched on to tales of illegal voters and the “deep state” and media witch hunts.

It’s a position that he believes has given him insight into how Trump thinks, Klepper told me in an interview for the latest episode of POLITICO’s Off Message podcast. “As a human, there are two things that I am desperately scared of: I’m desperately afraid of being called unkind and I’m desperately afraid of being called not smart,” Klepper said. And in every Trump statement, Klepper hears some version of, “‘You’re trying to delegitimize me and you’re trying to make me look dumb and not as popular. I’m not dumb; I’m popular.’”

The morning after we spoke, in apparent response to a Fox News segment about the questions Michael Wolff’s new book raises about the president’s mental health, Trump seethed in a series of tweets: “[T]hroughout my life, my two greatest assets have been mental stability and being, like, really smart. … I went from VERY successful businessman, to top T.V. Star ... to President of the United States (on my first try). I think that would qualify as not smart, but genius … and a very stable genius at that!”

Klepper sees the impulse behind tweets like that. “He’s the most famous person that has ever lived, and he wants a little credit,” Klepper said.

Even so, statements like those from the president of the United States—ostensibly the most powerful man in the world—pose a challenge for Klepper and other satirists: How do you parody reality that can feel like parody already?

Klepper got his break while pretending to be a journalist on “The Daily Show” with Jon Stewart, the comedy mainstay that billed itself as “the most trusted name in fake news.” In an era in which that term has become weaponized for political purposes, Klepper said that the question for writers and performers is “can you heighten the thing that already feels so absurd?”

“I think you can take the logic that got to that absurdity,” Klepper said, “you find … the tactics and … the ways in which they’re finding the crazy and use that in the premise and shake it up and multiply it by 10.”

But that gets harder not just because of the news, but because of how people are reacting to the news. The performers feel like the stakes are higher—“It’s an important time for comedy right now,” Klepper said—and he’s noticed that his audiences have grown more earnest over the year as well. The cultural division is obvious: In the studio or at home on their couches, they want blood, and the performers, eyes on applause and ratings, are complying. Late night comedy has become hours of Trump bashing, less of a release and more of a response.

Klepper grew up in Michigan and says that he has at least one relative back home who voted for Trump but who enjoys his show because to her it points to the obvious absurdities of the president without full-on bashing him. But he knows that’s not where most of the jokes are landing.

“I don’t think we want to be pigeonholed into preaching to that choir, but I also know that we are frustrated in one very similar direction,” Klepper said. “You feel the pull. People want something different than they wanted three years ago. They’re scared.”

The entire industry is struggling with what to do.

Dave Chappelle concluded a recent performance in Washington, D.C., recorded and released on New Year’s Eve as a special on Netflix, with an extended retelling of the story of Emmett Till, the 14-year-old boy who was beaten and drowned by a mob for allegedly whistling at a white woman in Mississippi in 1955. The woman who accused him, Chappelle recounted, admitted on her deathbed that she’d lied in her court testimony. Mad as that made him, Chappelle said, he also had to be grateful for how much the civil rights movement had changed the world, powered in part by the outrage over Till’s murder.

“That’s how I feel about this president … might be the lie that saves us all, because I have never felt more American than when we all hate [on him] together,” he said.

Click here to subscribe and hear the full podcast to hear the song Klepper listens to every night to get into character, and the media personalities he bases that character on.

In another performance released as a special the same day, Chappelle addressed comedians in the audience, calling this “the best time” to make jokes. “You have a responsibility to talk recklessly. Otherwise my kids may never know what reckless talk sounds like—the joys of being wrong,” he said.

For comedians, it's the best of times and the worst of times—more material than ever, more engaged audiences than ever, but also more people picking over the same already overexposed points.

“As a comedian, we say, ‘You have to connect with the audience, what are we all living through right now?’ Well, like it or not, it’s Donald Trump. There is that connection, and I think that helps with writing comedy because we’re all starting from that similar place,” Klepper said. “But we’re all looking at that as comedians, and I think that’s what’s really frustrating. It’s hard to find that nuance. It’s hard to continue to go after this. It would be nice to be able to choose what you cover as opposed to what you cover choosing you.”

I asked Klepper whether he finds what we’re living through to be funny.

“I find it mostly scary,” he said, of the chaos rippling through politics and government. “I sometimes get afraid that I get too complacent in how commonplace it becomes.”