Editor’s Note: This interview was conducted prior to a gunman attempting to assassinate Donald Trump. Following publication, The Daily Show announced that it had canceled plans to broadcast from Milwaukee. Klepper will also no longer be attending the convention.
Jordan Klepper’s first Republican convention as a correspondent for The Daily Show was in 2016, in Cleveland, when the party’s nominee was widely viewed as a rich source of comedy material but a hopeless candidate for president.
This week, Klepper is in Milwaukee with the Daily Show team covering the Republican convention, where former president Donald Trump will accept the nomination and be favored to win in November over President Joe Biden, who—as of this moment—remains the presumptive Democratic nominee.
“Twenty-sixteen does seem like a million years ago,” Klepper tells me. “I remember being in the arena when Trump gave his speech, with his 1984-size head projected in a way that was so fucking ominous. If you told me I was going to do this again eight years later and Trump would be the favorite, and gave me a tidbit about an insurrection in between, two impeachments, and a conviction—you know what, I can’t even get through this with a straight face.”
The Daily Show team has been hitting the road for the summer political conventions since 2000 (something I wrote about in The Daily Show: The Book). This cycle, “Indecision 2024,” brings the return of Jon Stewart, who was slated to host the show Thursday at Milwaukee’s Marcus Performing Arts Center. However, on Sunday, the show announced it would no longer broadcast this week from the city.
Klepper is accustomed to covering the MAGA circus on the ground. In a recurring segment, “Jordan Klepper Fingers the Pulse,” he has humorously and incisively captured the Trump faithful on the campaign trail, at CPAC, and outside a Manhattan courthouse. He even traveled among the right wing in Hungary, where there is kinship with the MAGA movement.
In an interview, which was conducted prior to a gunman attempting to assassinate Trump, and edited for length and clarity, Klepper talks about his role as a MAGA “anthropologist” and his plans for the Republican convention.
Vanity Fair: It’s been a bizarre few weeks in American politics. I thought I would cheer myself up by watching a bunch of your Daily Show bits. Didn’t work. They are plenty funny, but the subject matter is still depressing.
Jordan Klepper: If you’re looking for joy, maybe you need to go back to the silent film era.
The Daily Show staff and performers consume way more news than is healthy. How have you managed to stay sane all these years?
I feel very grateful that I can go into work and actually try to decipher all that’s happening with interesting, funny folks. We were off for a week and a half around the Fourth of July, after the first debate, and I was glued to my phone, reading all the ins and outs and the projections everybody had, just begging to get back into the studio to make a show or just to talk to some people about it, because my wife does not want to talk to me about it. My four-year-old is not at all interested in my witticisms. I’m ready to dive into talking about what a brokered Democratic convention would look like, but no, it’s Octonauts, Octonauts, Octonauts.
You’re about to head into the opposite extreme: all politics all the time at the Republican National Convention. The party’s nominee says Milwaukee is a “horrible” city, suffering from rampant violent crime. How are you planning to survive?
I’m a Midwesterner, and I will make it my mission to prove former president Donald Trump incorrect. I will ingest the cheese, I will drink the beer, and I will prove the horribleness of that city to be completely untrue. Frankly, the conventions are fun. It is such a surreal look at American politics. There’s going to be tanks on the streets. There’s going to be vengeance conversation on the inside surrounded by Midwest nice and people dressed as eagles. I’m stoked.
Yes, you grew up in Michigan. What do Michiganders give Wisconsinites shit about?
Football. College football, specifically. And we think we have better beer. But Michigan’s ire tends to aim more toward Ohio.
We’re talking several days before the start of the convention, and Trump has yet to unveil his pick for vice president. Who would be his funniest choice?
Mike Pence. Watching the sycophant Olympics has been compelling. Everybody has to grovel and eat shit to be Donald Trump’s VP. Whoever can bow the lowest and deepest will be picked. Mike Pence perhaps has the farthest to go. And I think he would be the embodiment of someone who, like, “This man tried to kill me, and I just would love to serve him again.”
Jon Stewart will “anchor” The Daily Show on Thursday, the convention’s final night, with correspondents taking turns earlier in the week. Which night will you be behind the desk?
I don’t know if the nights are set up yet.
They haven’t told you?
The parties don’t exactly know who all the candidates for president are now, so give The Daily Show a break, Chris.
That’s fair. If Biden were to quit, how hard would it be to stomach watching the Republicans do an end zone dance all week?
When you go out on the road, as I have, and talk to Republicans, they’re angry and they’re against everything and they’re against Joe Biden. It is a campaign built on one man’s vengeance. Suddenly that man is in the lead, and there are questions about who he’s running against. At the very least, the person he’s running against is diminished. Which leaves this week to be one in which they could articulate a future for a country that very well could be led by Donald Trump. And frankly, I don’t know what they’re going to say if Biden is gone. If you take away retribution and you have to replace it with innovation or a template for a working America—
Jordan—there is no chance of that at the Republican convention.
That’s not happening? Okay. Back to drinking New Glarus beer, then.
You mention being out on the road. You have explored a huge range of topics as a Daily Show correspondent, but your specialty has become interviewing hundreds of the MAGA faithful. Some of those conversations are funny, some are scary, but it’s clear you’re not doing them just for entertainment value. What, to you, is the point of those interviews?
Health insurance. Find a niche and just run it into the ground to keep me working.
Obviously, we are a comedy show. We’re looking for the funny. That is our bias. But it’s become revelatory for me. I feel more like an anthropologist. People develop ideas and opinions based on the things that their friends tell them and they never stress test in public. They're never asked how they got that idea. And so oftentimes I’m on the front lines of puncturing that bubble and getting to ask why, and in real time watching them have to work through an opinion that they develop but never stress test.
So what have you learned? At bottom, why do people believe in Trump?
If you turn on Fox News and you watch it for six hours straight, you’d be silly not to believe most of this stuff. And secondarily, you go to these events and they’re fun. When the parade comes to town, you show up. I’m a Michigan football guy. Ever gone to a tailgate? It’s fantastic. Why do people wear the colors of the team? One, it’s to support the team, but also it’s to be seen as a fan, to make connections with other people who are dressed as fans. And so you put on your team’s uniform and suddenly you’re not alone. We live in a time where we have a crisis of meaning. We don’t feel like our lives have any impact on others. And in many cases, we’re fucking right. We need that meaning in our life. And then some bozo who’s the most famous person on the planet, who ran the greatest country on earth, tells you that you’re not a bozo, that you are a patriot, and you are a hero, and you can serve your country by, I don’t know, attacking the Communists. That means something.
Have there been any times at Trump events where you felt at serious physical risk?
I mean, January 6 had plenty of moments of tension. I talked to a man swinging a pitchfork that day. The Stop the Steal rally, suddenly two people who were mad at me became 30 to 40 people who were mad at me and security had to take me down an alley and run me away to get into a car to go. So, not the kind of thing I expected I’d be a part of when I was taking improv classes.
There’s also an anthropological side to the club shows you and Roy Wood Jr. having been doing together. I saw one in Brooklyn recently where you explored the possibility of a coming race war. Always hilarious.
We’ve been calling the tour, “America: For the Last Time.” The shows are kind of open town halls, where we tell some jokes and we interact with the audience. And there’s no better feeling than walking out into the audience and seeing everybody’s butthole just clench up immediately, not wanting to talk to either one of us about what side they’re choosing in the race war. But you know what? Turn on the news. We’re in a weird, troubled time right now, so perhaps it’s good for us to have these difficult conversations when we can.
What’s the biggest difference between working with Jon Stewart the first time around and now?
He’s older. Boy, is he older. His body is falling apart. We’re having our own little DNC moment behind the scenes right now.
Should the Democratic nominee be someone other than Biden?
Yes. Both Joe Biden and Donald Trump are not fit to be president right now. That doesn’t mean there isn’t a better option between the two of them, but I think there are better candidates out there.
You don’t think it’s too late to switch?
Four months till the election? America can make people famous and unfamous in weeks. Ron DeSantis at one point was going to be the next president of the United States. And now I think he’s just outside screaming at Disney.
Okay, I give you a magic wand. Who do you choose for the Democrats?
I am most interested in Gretchen Whitmer. As a Michigan boy, I think she is thoughtful, she can speak to what people need, and she fixes the damn road.
And if Trump beats whoever the Democratic candidate turns out to be, where do you think comedians rank when it comes to being sent to reeducation camps? I’m figuring after Liz Cheney but before Cher.
As soon as we see Rosie O’Donnell being led away in handcuffs, I think it’s time for comedians to head to Saskatchewan. Who knows, maybe France is still an option. They’ve kept fascism at bay. Enjoy the press freedoms while we have them.
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