Jordan Klepper

Thanks in large part to Jordan Klepper, from 2005 to 2007 Chicago comedy connoisseurs had their Saturday-night plans locked down. They’d go to a party or check out an art show, then hurry over to the iO Theater, then located in Wrigleyville, just in time for the midnight performance of The Late Night Late Show. The weekly talk show featured local improv luminaries in character, guests such as Hoop Dreams director Steve James, and a lot of unabashed absurdity in the service of meticulously crafted conceits, such as an evening in which the show was hijacked by Russians.

Its host was the magnetic, deadpan, unflappable Klepper, whose new Monday­-through-Thursday program The Opposition With Jordan Klepper debuts on Comedy Central on September 25. Occupying the time slot following The Daily Show, on which Klepper was a correspondent for the past three years, The Opposition satirizes extremism and conspiracy theorists on both sides of the political aisle, with Klepper playing a character he’s described as “Alex Jones meets Garrison Keillor.” A cast of “citizen journalists” appear as wing nuts who just want to share their unsubstantiated opinions. The show, both onscreen and in the writers’ room, is dense with alums of Chicago’s comedy stages, including Late Night Late Show creator Seth Weitberg, Klepper’s frequent collaborator Steve Waltien, and multifaceted comedian Laura Grey (Klepper’s wife), as well as powerhouses such as Tim Baltz, Chelsea Devantez, and Asher Perlman. They’ve all been hard at work rehearsing in such glamorous places as the corner of their office conference room in New York City.

Klepper took a moment away from preparing for the premiere to talk over the phone about how his Chicago comedy education, especially The Late Night Late Show, prepared him to assume the host chair.

On The Opposition, you’ve brought in a lot of Chicago folks as writers and onscreen “citizen journalists.” Is there a particular perspective Chicago-trained comedians bring to a project?

I do think there’s something about the Chicago improv scene that breeds smart, thoughtful, collaborative people. My time at iO helped me become adaptive in the field [at The Daily Show], able to go with the flow and collaborate with people in morning meetings so small ideas could become big ideas quickly. It also helped me lose the idea of being precious about my own ideas and jump on other ones, which is a necessity in creating a show four times a week. It also made me curious. You have to be able to interpret the world around you in a way you find interesting so you become interesting onstage.

I came to Chicago from Kalamazoo, Michigan, right after college, following the one thing I knew I enjoyed. I wasn’t sure if I was going to be good at it. I was a math major and theater major and was still figuring out in college if I wanted to work in math or another field. But year after year I kept coming back to: What do I find most enjoyable and most freeing? I came to Chicago with the expectation of following through on a question I hadn’t answered.

Wait—you were a math major?

I was a nerdy kid who was pretty good at math, and I got a scholarship for it that paid for my college. [Laughs.] Humble brag. I like the ability to put things in order. At the same time, improv comes along and it forces you to embrace chaos. Those two things are really nice living side by side. Improv pushed me to be more curious; the mathematical side made me feel uncomfortable, but ultimately it was better for me. Life is a mixture of those two things. It’s both the brainstorming period where we can be free, but we also have to do a show in a couple-hour period, so it becomes all about editing, crafting an argument, functionally putting pieces in place. You have to use both sides of the brain.

How did The Late Night Late Show get started?

It was a while back. My memory has aged like a fine wine. It was Seth Weitberg’s idea to do a late-night show, and he wanted me to host it. It could function as a real late-night show, but also had characters that could recur. We were pretty young Chicagoans who had worked together in some way. From there, we had to grow up really quick. We had to figure out how to do weekly meetings, how to produce and write bits, how to create a world, what the rules were, et cetera. It couldn’t be an improv show where everybody just shows up. We’d meet twice a week to prep for that week’s show and hold rehearsal once a week to put together something that was fairly loose but ultimately had a structure that made sense for us. Each episode has a big theme to it, like, “This one’s going to tell the story of Hamlet.”

For one of our first meetings, Seth brought tapes of The Muppet Show. He wanted us to be inspired by its madcap fun, how it would see itself as a late-night show but immediately go off the rails.

Our guests were all over the map. When we had Jason Williams from the Chicago Bulls as a guest, we did the show like a basketball game—a halftime show, a scoreboard. We created a mascot called Desky that danced around. We also had Mr. Skin on at one point who was, um, a purveyor of celebrity nip slips. So we were making a smart, thoughtful show.

Why did Weitberg have you in mind to be the host?

I don’t know. I think I have the lanky build of somebody who should host a late-night show.

Being a host is great for people who want to be looked at all the time. It feeds that ego. It also adds pressure. You have to find the balance of how you perform, but also how you navigate the audience through the show in the way you want them to see it.

When you perform improv, it’s always the first and last show. It’s ephemeral.

That is the beauty of improv: You have to be there. It’s supposed to be in a sweaty basement existing for only that night. With that comes the danger of something being said that’s completely surprising.

What was it like arriving in Chicago with the goal of pursuing something intangible?

Part of what I was looking for was the ability to find a place to point me in the right direction. You can drive yourself crazy looking at other people’s trajectories and trying to emulate that. There’s no one way to find success. If you’re constantly looking to find something new, you’re hopefully moving in the right direction. Then there’s a lot of luck.

While in Chicago you were also a member of the improv troupe American Dream, which was known for coming up with its format just before going onstage. Watching the show felt like watching friends dick around.

Going out there and just doing anything was never really that freeing. Even though American Dream didn’t have a lot of structure, our most successful shows were the ones where we gave ourselves one construct to work within. We did a show once after Piero [Procaccini] had worked a double shift and was exhausted. So we said, “Piero, you’re going to sleep onstage. Literally.” So we did a show that was really quiet. We whispered. The audience raised their hands instead of laughing.   v

The Opposition With Jordan Klepper debuts on Comedy Central Mon 9/25 at 10:30 PM.