Insights into the live DNC episodes of “Daily Show” and “The Late Show” in Chicago

Insights into the live DNC episodes of “Daily Show” and “The Late Show” in Chicago

On Thursday morning, it’s adrenaline (and maybe a lot of caffeine) that fuels The Daily Show team in Chicago. And yet tonight marks what may be the most important episode of their entire week in town for the Democratic National Convention: a live episode hosted by Jon Stewart that airs at 11:30 p.m. ET.

Hopefully that means the show will go live around the time shortly after Kamala Harris finishes her acceptance speech for the Democratic presidential nomination at the United Center. But as her colleagues on CBS’s “The Late Show With Stephen Colbert” learned this week, the DNC isn’t promising to stick to a set schedule. “The Late Show” ran live episodes all week, meaning the show often didn’t air until around 1 a.m. local time — and Chicago’s Auditorium Theater was empty.

“I can’t imagine doing all the shows live!” says Jen Flanz, executive producer and showrunner of “The Daily Show,” as she prepares for Thursday’s show. “I love our live shows because they really convey the energy of what just happened. But we’re not a news show, and to comment on the news, you need a little bit of time to process it and write a more focused account of what happened the previous night. That’s what ‘The Daily Show’ does.”

“Being on the road can be very demanding, and then doing a live show, even at home, is a whole other level of effort,” she adds. “So, for others, I give a lot of credit to Colbert and that show. It’s a lot of live!”

It’s a lot of work for both shows, but here’s a little secret: For at least a week, the staff enjoys life away from home. For “The Daily Show,” the team meets every night to watch the convention in a hotel ballroom over pizza and beer and brainstorm ideas and jokes that are then fleshed out for the next day’s episode.

“We stay up all night and watch together,” says Flanz. “We split up at midnight and then meet up again at 8:15 p.m. – but that’s just how it is! It’s only a few shows. We’ll manage.”

“The Daily Show” is also taking next week off to regroup, which she sees as a light at the end of the tunnel as they battle through the week. “I’m like, ‘Let’s all just focus and keep going until we can’t anymore, which will hopefully be Friday morning,'” she says. “And then everyone is off.”

For Daily Show correspondent Michael Kosta, who hosted Monday night’s episode, the return to Chicago was a happy coincidence. He started with the show in 2017, when it also visited Chicago’s Athenaeum Theater for a series of episodes. Last time, he was the new guy. This time, he was behind the desk on the first night. (It was also a great pleasure to have Governor Gretchen Whitmer, from his home state of Michigan, as a guest.)

“It was humbling,” he says. “I didn’t really realise it until I arrived. Then I walked up those steps and thought, ‘I was here seven years ago as a brand new correspondent and now I’m at the top on Monday. Who knows where I’ll be in seven years?'”

Kosta met an extremely enthusiastic and large crowd at the Athenaeum, and Flanz says she’s seen firsthand now that there’s “a different vibe and energy at the DNC than there was a few months ago. So that’s great for us. But honestly, every time we tour with the show and go to a theater, the vibe is pretty good. People are really excited when you bring the show to their city.”

“I could say that the staff is probably more excited to do this than they would have been a few months ago because there are more jokes now,” she adds. “We’ve been doing Trump/Biden jokes for five years now. There’s a whole new storyline here, a whole new plot. So the show is exciting, not just for this week, but for the next few months leading up to the election.”

There was definitely a roar of excitement in the Auditorium Theater on Tuesday night, as about 4,000 “Late Show” fans erupted in applause and even a standing ovation as Michelle Obama and Barack Obama’s pre-DNC speeches were shown on screens. “Late Show” merchandise was sold throughout the massive venue ($40 for a T-shirt) and viewers patiently stood in long lines at concession stands to grab a drink while the broadcast was delayed due to DNC overruns.

“The Late Show with Stephen Colbert”
Scott Kowalchyk/CBS

That party atmosphere made for a raucous experience, especially when Colbert finally came out and answered a few questions from fans. “A lot of us got our start here in Chicago,” he told the audience, noting that he and his executive producer Tom Purcell met on the steps of The Second City improv theater in 1988. “I lived here for 11 years. How lucky we are to be back,” 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 the great food in this city, I will wear a slightly larger suit any day.”

Of course, broadcasting the show live also brings its own challenges – including when protesters interrupted the show that night during Colbert’s interview with former House Speaker Nancy Pelosi. A few minutes into his segment with Pelosi, a protester began shouting about the war in Gaza from the balcony.

Colbert had likely prepared for such a scenario and handled the situation calmly, even when it happened again in a second segment. Many protesters were in Chicago for the DNC, but others were just trying to rile up DNC attendees. On Monday, supporters of Robert F. Kennedy Jr. positioned themselves outside the Athenaeum with a megaphone and tried to get the attention of “Daily Show” fans as they entered the theater.

“We have strict security measures in place every night and hope that with these measures we can avoid (interruptions),” says Flanz. “Jon is hosting the live show and I am fully convinced that he will handle it with flying colors.”

The stars of the Daily Show had a chance to get to know Chicago better this week in segments such as Jordan Klepper’s Drinkathon with Illinois Governor JB Pritzker and the “InDogCision 2024: Rescuing Democracy” event around Chicago’s Wrigley Field, where fans met 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,” says Flanz.

Kosta adds, “Comedy is a tough business. There are a lot of ‘no’s,’ a lot of flops. This made me really happy and the week was a lot of fun. And let’s be honest: the weather helped a hell of a lot,” he says of the beautiful 21 degrees forecast for the week. “It’s fun to be in Chicago when the weather is good.”

But like beautiful days in Chicago, all things must come to an end quickly. And that goes for the late-night shows in the Windy City, too, which end Thursday night – just as Chicagoland prepares to say goodbye to hordes of Democrats and prepare for a sweltering, humid, 80-degree weekend.

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