The daily grind: Behind the scenes of ‘The Daily Show’ live in Chicago
A week of adrenaline and caffeine
By Thursday morning, the team behind “The Daily Show” is running on pure adrenaline—and perhaps a lot of caffeine—as they gear up for their biggest episode of the week in Chicago. The Democratic National Convention (DNC) has brought them to the Windy City, and tonight’s live episode, hosted by Jon Stewart, is set to air at 11:30 p.m. ET.
The unpredictability of live TV
The plan is for the show to go live right after Kamala Harris finishes her acceptance speech for the Democratic presidential nomination at the United Center. However, as their colleagues at “The Late Show With Stephen Colbert” have experienced, the DNC doesn’t always stick to a set timetable. “The Late Show” has been airing live episodes throughout the week, often not wrapping up until close to 1 a.m. local time.
“I can’t even imagine doing all the shows live!” says Jen Flanz, executive producer of “The Daily Show.” “I love our live shows because they really capture the energy of what just happened. But we’re not a news show, and to comment on the news, you need a little time to digest it and write a more focused take.”
The camaraderie of the team
Despite the grueling schedule, the team is thriving on the remote life. Each evening, they gather in a hotel ballroom to watch the convention over pizza and beer, brainstorming ideas and jokes for the next day’s episode.
“We stay up all night and watch together,” Flanz says. “We leave each other at midnight and then regroup at 8:15 a.m.—but that’s the road! It’s only a few shows. We can hack it.”
A light at the end of the tunnel
“The Daily Show” is taking the next week off to regroup, which has been a motivating factor for the team. “I’m like, ‘let’s all just focus and do it until we can’t do it anymore, which hopefully will be Friday morning,'” Flanz says. “And then everybody gets time off.”
A homecoming for Michael Kosta
For correspondent Michael Kosta, who hosted Monday night’s episode, returning to Chicago was a bit of serendipity. He started with the show in 2017 when it also visited Chicago’s Athenaeum Theatre for a series of episodes. This time, he was behind the desk on Night 1, with Michigan Governor Gretchen Whitmer as his guest.
“It was humbling,” he says. “It didn’t really hit me until I was flying in. Then I walked up these steps and I was like, ‘I was here seven years ago as a brand-new correspondent, and now I’m at the helm on Monday. Seven years from now, who knows where I’ll be?'”
The energy of the DNC
Kosta encountered an extremely enthusiastic crowd at the Athenaeum, and Flanz notes that the DNC has a “different vibe and energy than it would have a few months ago.” This excitement is palpable, not just for this week but for the next few months leading up to the election.
The ‘Late Show’ experience
Over at the Auditorium Theatre, about 4,000 “Late Show” fans erupted into applause and standing ovations as Michelle and Barack Obama’s DNC speeches were shown on screens. The venue had a party atmosphere, with merch being sold and long concession lines for drinks.
When Colbert finally came out, he answered a few questions from fans. “Many of us started here in Chicago,” he told the audience, noting that he and his executive producer Tom Purcell met at The Second City improv troupe theater in 1988. “I lived here for 11 years. How lucky are we to be back here.”
Handling the unexpected
Live shows come with their own challenges, including when protesters interrupted Colbert’s interview with former House Speaker Nancy Pelosi. Colbert handled the situation calmly, even when it happened again in a second segment.
“We do have tight security every night, and we hope that with that in place we can avoid interruptions,” Flanz says. “Jon’s hosting the live show, and I’m fully confident that he would handle it with grace.”
Engaging with the city
“The Daily Show” stars got a chance to dig into Chicago through segments like Jordan Klepper’s drinkathon with Illinois Governor J.B. Pritzker and the “InDogCision 2024: Rescuing Democracy” event around Wrigley Field, where fans met the news team while registering to vote and adopting dogs.
“People were so excited to meet our talent, it just blew me away,” Flanz says.
A week to remember
For Kosta, the week has been a lot of fun. “Comedy is a hard business. There are a lot of ‘nos,’ a lot of bombs. So this has made me really happy,” he says. “And let’s also be honest. The weather has been really helping,” he adds, referring to the week’s beautiful 70-degree forecasts. “It’s fun to be in Chicago when there’s good weather.”
But like all good things, the late-night shows in Chicago must come to an end. As the team wraps up on Thursday night, Chicagoland prepares to say goodbye to the hordes of Democrats and get ready for a scorching, humid, 90-degree weekend.
For more information on “The Daily Show,” check out the trailer. For “The Late Show With Stephen Colbert,” visit the trailer.