Inside Chicago’s Own Late Night Show, ‘The Late Live Show’

In retrospect, it just seems so obvious.

After a few minutes of talking to the people behind Chicago’s The Late Live Show, one starts to feel like the relevant question isn’t, “Why did these guys decide to start a live, untelevised talk show?” The real question seems to be, “Why isn’t everyone else doing it?”

“There are stand-up shows, there are improv shows, and there are sketch shows in Chicago,” said Joe Kwaczala, the show’s 25-year-old host. “Those are formats people are familiar with and can dial into. But so is a late-night talk show! We thought, ‘Why isn’t there one you can go out and see live?’”

Since 2010, Kwaczala and a handful of collaborators have used that creative optimism to build a live experience that regularly draws sold-out crowds to their rented black-box theater space. Unsurprisingly, it’s a very do-it-yourself affair, meaning the set usually just consists of a talk show’s bare essentials: a couch and a desk. In lieu of a teleprompter, they have a laptop in the front row, facing Kwaczala.

“We put the show together with duct tape and hope it works,” said producer Brandon Hauer. “People see the effort that goes into replicating a talk-show format on stage, and it makes people fans. They want to see us succeed.”

Despite its creators’ thriftiness, The Late Live Show is struggling. It’s in the final days of a Kickstarter campaign to raise cash for renting their venue (and thus keep ticket prices at $5 or lower) and buy a decent musical amplification system (to keep attracting local bands that might otherwise never have a shot at a talk show).

The show’s 13 staffers are hoping to raise $3,361 before the start of their next run at Chicago’s Stage 773 theater. Every few months, The Late Live Show has a “season” of Saturday night shows, usually running about six weeks. This will be their fifth season, and the previous four have brought them increasingly high-profile guests, from Community’s Danny Pudi (“That sold out in a couple of minutes,” Hauer recalled) to championship pro wrestler Colt Cabana. The A.V. Club’s head writer, Nathan Rabin, has become a regular guest and a fan: he told me the staff are “true students of comedy with a deep reverence for the medium’s history and Chicago’s distinguished place within it in particular.”

And, indeed, live comedy remains the show’s centerpiece. Like any self-respecting late-night show, each performance begins with a monologue from a suit-and-tie-wearing Kwaczala. The monologue jokes have a rhythmic formula that should be familiar to any viewer of Conan or Leno: Kwaczala introduces a goofy current event, the audience giggles, he nods, then he delivers a knowing “Yeah,” followed by a punchline. But even here, the writers try to push the envelope, while still being reverent of the format.

Take, for example, an April monologue joke about Ted Nugent’s run-in with the Secret Service. The punchline begins with a bit of an eye-roller: “Yeah, the Secret Service report that there’s no reason to be alarmed; that while he may have a gruff exterior, he also has a soft, Nugent-y center.”

But then, after the audience laughs and groans, an image of a Baby Ruth candy bar appears onto the back wall and a voice plays over the PA: “That last joke was brought to you by Baby Ruth, the Ted Nugent of candy bars: it’s a little nutty and it looks like a piece of shit.”

When he’s at the desk, Kwaczala has a confidence that gives him the air of a much older TV veteran. He smirks and taps his pen on his desk with the best of them, and he never approaches his hosting persona with any kind of ironic wink. He has a remarkable ability for calm improvisation in his interviews, which are usually (and of necessity) with Chicago locals who have little to no national renown.

That local flair means the show was an unexpected cultural education for Kwaczala and his co-creators, CJ Toledano and Andrew Smreker, all of whom immigrated to Chicago to study at Second City.

“In researching for guests and musical acts, you have to dig into this question of, ‘What other parts of Chicago is the city famous for? Who are the musicians and the personalities around here?’” said Toledano, who left the show last year and scored a writing gig at Late Night with Jimmy Fallon. “That was a part that we didn’t know we were going to learn about.”

And what would a late-night show be without sketches? A cross-section of young men and women from the Chicago comedy scene – improv performers, stand-ups, writers for Groupon – crank out bits that tend toward the surreal.

Take a recent one, in which co-host Joe McAdam introduces The Late Live Show’s “sworn defender,” “Toblerine,” who looks like a guy in a dimestore Wolverine mask with sticks of Toblerone where his claws should be.

“Couple things about me,” Toblerine says, launching into a PowerPoint presentation about why a woman should “do” him. “My dick is not made of chocolate. This isn’t so much a reason why you should do me, but I’m sure it’s a concern. It ejaculates normal, healthy semen. Quite a lot of it, actually. No worries there.”

Many of the sketch premises involve pop-culture touchstones – defunct Nickelodeon game shows, Frasier, Val Kilmer – that show off the staff’s status as twentysomething Millennials. Indeed, Conan O’Brien – not Carson or Letterman – was the mutual idol that united the show’s three originators.

For decades, a writing gig on a network talk show has been a holy grail for aspiring comedians. “We talked about how much we wished we could write for those shows,” Kwaczala recalled. “We thought, ‘Well, instead of waiting around to hopefully one day write for a late-night talk show, why can’t we just start one up?’”

But despite its televised inspiration, The Late Live Show was not invented to be on the air, even though the staff regularly posts recorded clips on their YouTube page. “These days, everybody puts things up online with the hopes of being the next big thing and being discovered,” said Toledano. “But we’re all live performers. Our focus is to make it a great stage show.”

Kwaczala isn’t quite as militant about the format, but he’s firm about the show’s ethos.

“If The Late Live Show was ever on TV, it would mostly be to get young comedy fans to be like, ‘What’s this weird thing? I like this weird thing,’” he said. “That’s my dream.”

Photos by Aziz Oz Lalani.

Abraham Riesman lives in Manhattan, where he Tweets, Tumbls, and is working on a campaign to arrest LMFAO.

Inside Chicago’s Own Late Night Show, ‘The Late Live […]