By Thursday morning, it’s adrenaline (and perhaps lots of caffeine) that’s fueling “The Daily Show” team in Chicago. And yet, tonight is perhaps their biggest episode of their entire week in town for the Democratic National Convention: A live episode, with host Jon Stewart, set to air at 11:30 p.m. ET.
Hopefully that means the show will go live around that time just after Kamala Harris finishes her acceptance speech for the Democratic presidential nomination at the United Center. But as their colleagues at CBS’ “The Late Show With Stephen Colbert” experienced this week, the DNC makes no promises of sticking to a set timetable. “The Late Show” went with live episodes throughout the week, which means it often wasn’t going off the air — and clearing out Chicago’s Auditorium Theatre — until close to 1 a.m. local time.
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“I can’t even imagine doing all the shows live!” says “The Daily Show” executive producer/showrunner Jen Flanz, as she preps for Thursday’s show. “I love our live shows because they really infuse that energy of what just happened. But we’re not a news show, and in order to comment on the news, you need a little bit of time to digest it and write a more focused take of what the previous night was. That’s what ‘The Daily Show’ does.
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“Being on the road can take something out of you, and then doing a live show, even at home, is exhausting in a different way,” she adds. “So, for others, I give Colbert and that show a lot of credit. It’s a lot of live!”
It’s also all a lot of work for both shows, but here’s a little secret: At least for one week, the staffs are thriving on living and breathing the remote life. For “The Daily Show,” the team is gathering each evening to watch the convention in a hotel ballroom over pizza and beer, putting together ideas and jokes that are then fleshed out for the following 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 — but that’s the road! It’s only a few shows. We can hack it.”
“The Daily Show” is also taking next week off to regroup, so that’s been a light at the end of the tunnel as they power through the week. “I’m like, ‘let’s all just focus, and do it until we can’t do it no more, which hopefully will be Friday morning,” she says. “And then everybody gets time off.”
For “The Daily Show” correspondent Michael Kosta, who hosted Monday night’s episode, there was a bit of serendipity in returning to Chicago. He began with the show in 2017, when it also visited Chicago’s Athenaeum Theatre for a series of episodes. Last time, he was the new guy. This time, he was sitting behind the desk on Night 1. (There was also a thrill in having Gov. Gretchen Whitmer, from his home state of Michigan, 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?”
Kosta encountered an extremely enthusiastic and large crowd at the Athenaeum, and Flanz says she has seen first-hand now how the DNC has a “different vibe and energy than it would have a few months ago. So, that’s great for us. But honestly, every time we take the show on the road and go to a theater, the vibes are pretty good. People are really excited when you bring the show to their town.
“I could say the staff is probably more excited to do this than what it would have been a few months ago, because there’s more jokes now,” she adds. “We did Trump/Biden jokes for five years now. There’s a whole new storyline, a whole new plot here. So for the show, there is an excitement, not just for this week, but for the next few months, leading up to the election.”
A thunderous enthusiasm could definitely be felt over at the Auditorium Theatre on Tuesday night, where about 4,000 “Late Show” fans erupted into applause and even standing ovations as Michelle Obama’s and Barack Obama’s DNC speeches were shown on screens. At the massive venue, “Late Show” merch was being sold ($40 for a t-shirt) and audience members were patiently standing in long concession line queues for a drink to pass the time while the broadcast was pushed back due to DNC overruns.
That party atmosphere made for a raucous experience, particularly when Colbert finally came out and answered a few questions from fans. “Many of us started here in Chicago,” he told the audience, noting that he and his exec producer Tom Purcell met on the steps of The Second City improv troupe theater in 1988. “I lived here for 11 years. How lucky are we to be back here,” Colbert said. “I left here 30 years ago. And the city is even more beautiful than the last time I was here. In honor of how great the food is in this city, every day I’ll be wearing a slightly larger suit.”
Of course, doing the show live comes with its own challenges — including when protesters interrupted the show that night during Colbert’s interview with former House Speaker Nancy Pelosi. Several minutes into his segment with Pelosi, a protester began shouting from the balcony regarding the war in Gaza.
Colbert had likely prepared for such a scenario, and handled the situation calmly, including when it happened again in a second segment. Plenty of protesters were in Chicago for the DNC, as well as others just looking to get a rise out of DNC attendees. On Monday, supporters of Robert F. Kennedy Jr. were stationed outside the Athenaeum with a bullhorn, attempting to grab the attention of “The Daily Show” fans as they entered the theater.
“We do have tight security every night, and we hope that with in place we can avoid [interruptions],” Flanz says. “Jon’s hosting the live show, and I’m full confident that he would handle it with grace.”
“The Daily Show’s” stars got a chance to dig into Chicago this week via segments such as Jordan Klepper’s drinkathon with Illinois Gov. J.B. Pritzker, as well as a “InDogCision 2024: Rescuing Democracy” event around Wrigley Field in Chicago, where fans met the “The Daily Show” news team while registering to vote and adopting dogs.
“People were so excited to meet our talent, it just blew me away,” Flanz says.
Adds Kosta: “Comedy is a hard business. There are a lot of ‘nos,’ a lot of bombs. So this has made me really happy, and the week has been a lot of fun. And let’s also be honest. The weather has been really fucking helping,” he says of the week’s beautiful 70-degree forecasts. “It’s fun to be in Chicago when there’s good weather.”
But like nice weather days in Chicago, all things must quickly come to an end. And that includes the late night shows in the Windy City, which wrap on Thursday night — just as Chicagoland prepares to say goodbye to hordes of Democrats and get ready for a scorching, humid, 90-degree weekend.
