Jordan Klepper interviews a Trump supporter in the run-up to the 2024 election on ‘The Daily Show.’

Jordan Klepper is more determined than ever to wrap his mind around the MAGA mindset. A Daily Show correspondent since 2014 (with a two-year hiatus at the start of Trump’s first term that yielded the TV special Jordan Klepper Solves Guns and his own late-night news satire, The Opposition), Klepper is currently one of the storied program’s regular rotating hosts. That is, when he’s not commanding a stage somewhere for his Suffering Fools tour, which swings through Cedar Rapids’ Paramount Theatre on Friday, Oct. 17.

Klepper said he crafted the โ€œbig old showโ€ around his experiences at The Daily Show, questions he often gets from everyday Americans while on the road, and takeaways from his many interviews with folks inside the MAGAsphere for his “Jordan Klepper Fingers the Pulse” segments.

โ€œHopefully I can tell some stories and some jokes that can bring a little bit of sunshine into these weird, dark times,โ€ the Kalamazoo, Michigan native told Little Village in a phone interview on Wednesday.

โ€œIt’s sort of an attempt to get a bunch of people in the room together and commiserate around the stuff that we’re angry about,โ€ he continued. โ€œAn added bonus for the show in Cedar Rapids and for some of these shows I’m doing on the road is I’m bringing along Langhorne Slim, who’s this great musician โ€ฆ We feel so isolated and pulled apart from our communities, I was like, โ€˜if I’m coming to town, I want there to be a music show where people can stand up and clap and feel like they’re a part of something,โ€™ and Langhorne brings that spirit of Woody Guthrie and a little bit of moving and shaking that I think will be welcome.โ€ 

The following interview has been edited for length and clarity.

I know you have a background in improv with the Upright Citizens Brigade. How has that part of your career translated into working on a project like The Daily Show with a team of writers and comedians? Has improv prepared you for this kind of collaborative environment in TV?

It definitely has. Improv has been a big part of my comedy life, and my life in general. When I got to The Daily Show, when you’re writing for stuff that’s on the show that day, a big part of that is saying yes to ideas and creating something out of nothing, which is a bedrock of improvisation, and then cut the stuff in the field. That, to me, is where my improv training comes out. We prep for points of view and takes and what people might say in the field, but you really go walk out there and have to essentially improvise with a scene partner out there in the field โ€” talk, respond, listen, find some humor and some hypocrisy wherever you can. That was what I was taught in Chicago and New York, which is, stay open and curious and see if you can find the funny and the interesting.

How is it working with scene partners who don’t necessarily know they’re part of the scene, and are maybe even trying to work against you? 

Yeah, in some ways, they are unwitting scene partners. But I spent 10 years doing improv shows at the back of bars in Chicago with people of all different stripes and improv capabilities. So I’m ready to have scenes with people all across America, whether or not they’re yes-and-ing me or not.

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I’m curious what you think about the dark-sided version of what you do: the big right-wing sphere of people who do man-on-the-street interviews at, like, liberal protests, and then deceptively edit them to make it look like they โ€œtotally ownedโ€ some 20-year-old. Maybe they’ll pretend it’s comedy, or they’ll pretend it’s news, or somewhere in between, and it can be quite lucrative.

Man-on-the-street has been around for quite some time, and so it’s not a new phenomenon. I do think, in this day and age, where everybody’s stuck in their phones reading about what’s happening in the world but not actually experiencing it, there’s always a hunger for seeing what people are actually responding to and feeling and thinking. So I get why people are drawn to man-on-the-street interviews. I get why they’re drawn to Daily Show pieces and โ€œFingers the Pulseโ€ because we’re going to places and we’re talking to people. 

You will always have people who use that in ways that perhaps are more deceptive than others. The cottage industry of people trying to own one another online is perhaps not great for political discourse, but definitely gets the clicks, and that’s something that’s part of this political conversation right now, for better or for worse. 

For us at The Daily Show, what we always do is we’re pretty open about our bias. Our bias is towards what is funny and what is interesting and curious, and so we’re always chasing what is compelling, what is hypocritical, and trying to find a way to bring that to an audience who hasn’t heard that from their family members, but maybe now gets to see it in the fields of America.

Jordan Kleppler interviews Trump supporters ahead of the former president’s Oct. 9, 2021 rally at the Iowa State Fairgrounds in Des Moines. โ€” ‘The Daily Show with Trevor Noah’ still

Even though serious times are still very funny, I’m curious what the conversations are behind the scenes working on a story like Jimmy Kimmelโ€™s suspension. I wanted to be a fly on the wall when that Sept. 18 episode was produced!

I think a lot of people in America right now feel very, very scared, stressed out and at their witโ€™s end looking at the news and seeing what’s happened across this great land of ours. And what I feel really lucky for is that we get to go into work and try to make something out of it. So when Jimmy Kimmelโ€™s show was pulled off the air, that was obviously a big conversation that we all had. I think there’s a lot of camaraderie and support for the other late night shows. We know how hard this job is. We know the people who work there work at a lot of these shows, and how they’re just trying to find humor and speak some truth to power, but also just find jokes where they can. 

To see essentially an administration try to bully comedy and limit what is said is infuriating and scary. So to be able to come into work and talk about that is a real joy. That show in particular, to be able to find a comedic take on it, and to indulge in this idea of what state-run TV would be like, suddenly opens up so many fun ways to explore a dark topic. At The Daily Show at its best, we’ll find those spaces where itโ€™s not just standing up on some pulpit and screaming about how angry you are. It’s finding a way to embody that chaos and find some humor in it.

Even on those really dark, dark days, what we look at is not only the news, but how the news is told. We start the day in a room and just start talking about what we’ve seen from the night before. We watch clips together, react to those in real time, try to find what is humorous about it, but also where the bullshit lies. Hopefully, with a group full of smart people who are comedians and satirists, we can find ways to speak to the presentation of the news beyond just the news itself.

What have been some of your most memorable interviews โ€” maybe a time where you were really shocked by what played out?

There’s a lot of moments that stand out. I was in Washington D.C. once, and an insurrection broke out. So that was surprising to me, to suddenly see a bunch of people break into the Capitol and try to overthrow the government. It was a thing to behold. 

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Sometimes people are remarkably candid and open. I often think about an interview I did after the first Trump impeachment: Trump was stopping people from speaking, specifically withholding John Bolton from speaking out about his point of view and what had happened. I remember talking to somebody on the road about the impeachment, and she started telling me about how Trump is so transparent, and if he was guilty, he would be stopping people from talking. If he was blocking people from speaking, that would sort of be an admission of guilt. She doubled down on it. Then I corrected her and let her know, well, that’s exactly what he was doing. She takes this really long beat to think about it, really contemplate it, and just responds, โ€œI don’t care.โ€ It was one of those moments that kind of cut through all of the noise, in some ways.

The politics and the arguing that we have out here on the road feels like a debate, but really what we’re feeling is identity, and Trump means something else. And she was going to defend him no matter what, whether he was right or wrong about this thing. He was who she loved and supported. It’s those moments, to me, that are really surprising and cut through through the noise. [Editor’s note: This interview happened in Des Moines in early 2020. It begins at the 3:07 mark in the video below.]

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When you drop the irony and the sarcasm, the images that are happening in places like Portland and Chicago are pretty shocking to me. There are elements of the MAGA movement that are so based on cruelty, and I’d like to believe thatโ€™s not part of the American character, but I see some of these images, these stories of kids being ziptied, and itโ€™s awful. 

I’d like to think, and I’d like to hope, that images of depraved acts of humanity like those actually shake people. How do I get at that through some comedy? That’s a bigger question. I’m going to need to work on that. But as a person and as a citizen, that’s the thing that I’m most curious about: do we truly yearn for these types of images, and can’t we find some common ground in being disgusted by the stories that we’re hearing?

I think comedy definitely has a place. I’ve seen the images out of Portland with an inflatable frog suit on the front lines, facing down ICE. There’s something striking about that, that bold use of comedy.

I think you’re totally right. It seems to be a provocation to try to create images of World War II, as Donald Trump would put it. So people who are comedically dressed up in inflatable costumes poke a hole in this propaganda. So kudos, kudos to those people who understand humor and how to wield it.ย