The NPR Network will be reporting live from Chicago throughout the week bringing you the latest on the Democratic National Convention.

In a way, this week’s Democratic National Convention in Chicago might be the event that Jon Stewart predicted six months ago – or at least, hinted at with a wink and a few devastating one liners.

That’s when Stewart kicked off his current stint at The Daily Show, hosting once per week after nearly nine years away. During his first episode in February, he asked questions and poked fun at President Joe Biden’s persistent public flubs amid questions about his age.

Stewart joked about former president Donald Trump’s age too, noting that he and Biden “are the oldest people ever to run for president, breaking by only four years the record that THEY SET THE LAST TIME THEY RAN!” But his words about Biden brought rebukes back then from liberals like the former president’s niece Mary Trump, Keith Olbermann and hosts on The View.

Still, even though Biden now has left the presidential race to make way for younger Vice President Kamala Harris, Stewart says he’s not feeling particularly vindicated or prescient.

“The whole gig is to not allow the noise of the crowd or the pressure of what you might imagine the reaction to something, to sway that kind of internal barometer that we’ve developed at the show of what’s salient, what’s absurd, what’s jumping out at you,” Stewart said in an interview before the DNC began.

It’s a job that’s taken on even larger proportions this week, as The Daily Show presents episodes filmed before an audience of more than 800 people in Chicago at the convention — featuring a different correspondent hosting every night. It all culminates with a live show hosted by Stewart on Thursday.

Stewart and executive producer/showrunner Jennifer Flanz sat down to talk about The Daily Show at an important time for the program. The show and its offshoots earned a total seven Emmy nominations this year for a season where they welcomed a succession of guest hosts — from Leslie Jones and Sarah Silverman to Charlamagne tha God and Michelle Wolf – before settling into the current pattern of Stewart hosting once a week and the correspondents taking over the other nights.

Flanz, who started working on The Daily Show before Stewart did – starting as a production assistant in 1998 – said it was probably necessary for the show to have the experience of supporting many different hosts first, so they could make the current iteration work well.

“I do think this is the best version of the show that we could make,” added Flanz, noting it is too early to know if that means the show will delay or suspend seeking a permanent full-time host.

Jennifer Flanz at the 2018 Tribeca Film Festival.

Andrew Toth/Getty Images

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Stewart, who seems recovered from a bout with COVID that kept him from hosting a few weeks back, says he hasn’t yet decided if he will keep going after the presidential election in November. Right now, the comic says he’s mostly hoping to encourage correspondents like Michael Kosta, Desi Lydic, Jordan Klepper and Ronny Chieng, who have grown into their roles as hosts.

Our conversation has been edited for length and clarity.

We saw you guys decide not to bring the show [to the RNC] because of security reasons. What’s different that’s allowed you to go ahead with shows at the DNC?

Jennifer Flanz: [At the RNC] we had built a set and we were ready to go. And then the assassination attempt against Trump happened and the whole city felt like it was on lockdown. And we were like, ‘How are we supposed to get an audience?’ Getting the audience into the theater felt like it was going to be very hard. It just felt like, in order to make sure we could get shows on, we should go back to the studio … [At the DNC] we are, at least, very far from the convention center. Our theater is very far from where the security is.

I can imagine for journalists what the value is in going to the actual place … But can you talk a little bit about why it makes sense for you guys to have the whole [show] move to the DNC as opposed to just sending some of the correspondents?

Jon Stewart: A lot of it is Comedy Central just trying to burn off airline miles [laughs]. I can tell you, some of the best material that we’ve gotten over the years has been at the conventions. And Jen and I have been doing this since 2000 … getting the correspondents on the floor, interacting at the convention center … John Oliver wouldn’t even have met his wife if we had not gone there.

Flanz: He made a love connection at the convention. [Famously, Oliver’s now wife Kate Norley, met him while helping the comic hide from security at the 2008 RNC while he was working for The Daily Show.] 

Stewart: It adds a level of urgency and immediacy to the comedy that you wouldn’t get standing in front of a green screen … And we’ve done that, too.

Flanz: We also have the ability to have multiple correspondents doing a piece together … So it feels like you’re in the news rather than just making fun of it.

Jon, on the nights that you’re not hosting [at the DNC], will you also be helping out?

Stewart: I think my job at some level has become like an old man [in the] corner trying to … let everybody know like, ‘Hey, don’t don’t feel the pressure of this, or don’t stress too much about that. Like, you guys know what you’re doing.’ And that’s been the most impressive thing to me, is watching … Jordan and Desi, Michael and Ronny as they kind of accelerate their growth as hosts as well.

Flanz: I think Jon gets them a lot of confidence … in believing in their own opinion and getting out there. And it’s okay to say things that you want to say, but also not say everything if you don’t feel like saying it.

Stewart: Well, that’s the biggest thing.

Flanz: You don’t have to comment on everything.

Stewart: Sometimes there’s this sense of, ‘Oh, we have to go out there with a profound commentary on there.’ And it’s like, no, actually.

That was one of the toughest things about the show, is that it had created this expectation that whenever there was tragedy or something devastating, that we were going to have to go out there and contextualize it in a way that, you know, eases the burden for people.

When you returned to the show, your first commentary was about Joe Biden and Trump and age. How do you feel now that we’ve reached this point where [Biden] had to leave the race? Do you feel at all vindicated? 

Stewart: You know, I don’t know that I would ever look at it as vindicated … That’s kind of the whole gig, is to not allow the noise of the crowd … to sway that kind of internal barometer that we’ve developed at the show of what’s salient, what’s absurd, what’s jumping out at [us]. How can I articulate this, you know, elephant in the room that I’m seeing … how do we frame it and how do we present it in a way that doesn’t take it out of context, but allows people to see it clearly, laugh at its absurdity and digest it?

When we first got in there, my first thing was like, ‘Hey Jen, why don’t we do this: Israel/Palestine, first episode.’ And Jen was like…that might be kind of a very narrow swing. Why don’t we step back a bit? We’ve got our Indecision [election] coverage – why don’t we set the parameters for the race?

Flanz: We hadn’t been on the air for over two months…When we found out Jon was coming back, we just needed to set up for the audience, what are we working with here and what is this year going to look like for The Daily Show? That was [Stewart’s return episode], which set up a lot of criticism from all sides…[people] saying Jon’s more liberal, Jon’s more conservative…but we’ve always been this way…If Jon or Desi or Michael and the hosts aren’t saying exactly what the audience wants to hear and feel…they’re never going to be satisfied.

You know, I interviewed Dulce Sloan some time ago, and she said when she heard that Jon was coming to the show, she just felt like, ‘Okay, now we won’t get canceled.’ … I’m wondering if there was a sense of that, too, in what’s happened here – that the show needed a little help and Jon was able to come back.

Flanz: I wasn’t afraid we were getting canceled … [But] we were in this place where we didn’t know what was going to happen with the show. And had been pitching a bunch of concepts and ideas. So Jon walking into the studio, people were so happy …the relief of like, ‘Oh, that’s the next chapter.’

Stewart: The difficulty for the show is that they’ve been doing a point of view show … a machine built for a perspective. And they’ve been doing it through the eyes of guest hosts, different celebrities, which might be one of the hardest things to pull off. Now they get to refocus on the show’s point of view, because the [correspondent] hosts are steeped in that culture. They know the machine.

So when [your return] was announced, of course, we were told you were going to do it at least until the election. Do you know if you’re going to keep doing it after?

Stewart: I do not. But, you know, I think right now we’re just sort of in the middle of everything that we’re doing. And when we get through it, I think Jen and I’ll probably sit down and talk about next steps.

Flanz: We’re a daily show. We barely think a day or two in advance.

Stewart: [November] just seems ages away.

Are you in a situation where The Daily Show doesn’t need a permanent host?

Stewart: It’s not so much about a permanent host. It’s about, is there an organic transference to this one individual? I feel like the show’s clicking, whatever that means. There’s always a tendency to look at, ‘What’s the next iteration?’ But we’re iterating that right now.

Flanz: It’s fun and I think we’re making great shows. For people who are on social media all the time, which is a lot of our audience, seeing different faces and hearing different voices is cool for them and exciting. I know there is a standard in late night, which is one host. But we’re breaking that, and it’s working. So who knows? Let’s see if we can get through the [DNC] week.