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.
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.
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.”
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.
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.
