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.

On a bench near the Santa Monica Farmer’s Market in July, Peggy Cheng recalled the time a television writer pitched her a wacky sitcom centered around the unlikely scenario of a young woman who had befriended her elderly neighbors.

Cheng, who was working in TV development at the time, wasn’t impressed.

“She thought it was so unique and I was like, ‘Hmm,’ ” said the 40-year-old Brentwood resident, laughing.

After all, the writer could have been describing Cheng’s life. Her best friend, Karen Lektzian, lives in the unit above hers and is 24 years her senior. They even had a meet-cute: A leaky toilet brought them together. But their difference in age has not stopped the two from being active participants in each other’s lives. Cheng spent months helping Lektzian plan her wedding. Lektzian picked Cheng up from the hospital after surgery. And they’re both always up for a last-minute trip to the local Ralph’s.

“I share everything with her,” Cheng said. “She’s one of the few friends who knows every facet of my life.”

Lektzian, a retired IT consultant, says the feeling is mutual. “Life is more fun when we’re together. I think that sums it up.”

As it turns out, age-gap friendships like Cheng and Lektzian’s may be more common than many of us think. A 2019 AARP survey found that nearly four in 10 adults have a close friend who is at least 15 years older or younger than they are. Even more are interested in cultivating these types of friendships. Nearly eight in 10 adults want to spend more time with people outside their age groups, according to a report from the Washington, D.C.-based organization Generations United.

Although research on the benefits of intergenerational friendships is nascent, several studies suggest that older adults who regularly interact with younger people experience less anxiety, depression and cognitive decline than their more age-siloed peers. For younger folks, having friends outside their generation may help reduce both internal and external ageism, and address feelings of isolation and loneliness.

“From both sides there are individual level benefits that have the potential to improve health and well-being,” said Lauren Dunning, director of future of aging at the Milken Institute.

But ask those who are in age-gap friendships what they like about it, and chances are they’ll simply tell you they are in it for the enjoyment and pleasure of spending time with someone who “gets” them.

“There’s this exchange of ideas and knowledge, and this recognition that having fun is just as much a part of later life as it is for younger life,” said Catherine Elliott O’Dare, a professor in social policy at Trinity College in Dublin who studies the benefits of intergenerational friendships.

We spoke to six intergenerational friend groups in L.A. about how they met, what they do together and the benefits of their age difference.

Justin Beverly, 26, student. Jose Bautista, 73, retail worker. Nicholas Baraban, 33, retail worker

How did you meet?
Bautista: “We all used to work at the Hobby Lobby and these guys used to have beers after work. One day I invited myself along, but on one condition — we have to play [music].”

Favorite activities:
Playing music, going to the batting cage, open mic nights, barbecues.

What makes the friendship special?
Baraban: “I had a best friend who passed away — a bandmate. Jose helped me start playing with other people again. He was the first person I opened up to about playing out again.”

Bautista: “We’ve become best friends. I can rely on these guys for anything and I know they’ll come through. And me too. They can count on me for anything.”

Best part of being in an age-gap friendship?
Beverly: “Getting everyone’s perspective and point of view. People have more stories to tell from different times. It gives an interesting dynamic.”

Bautista: “I don’t feel an age difference with them. I don’t know how a 73-year-old is supposed to act.”

Baraban: “I don’t feel an age difference so much.”

Friends Jeannine Ball, 69, left, and Antoine Cason, 38, sit in the bleachers of Lakewood High School’s football stadium in Lakewood.

(Christina House / Los Angeles Times)

How did you meet?
Ball: “My son Josh was a waterboy for the football team at Los Alamitos High. Antoine walked past us before school one morning and says, ‘Hey J-Dub. How are you doing?’ I said, ‘Who was that?’ and he said, ‘That’s the nicest guy on the football team.”

Cason: “Then I took your photography class senior year and after I went to college I’d come back and see everyone and it just grew from there.”

Favorite activities:
Football activities, going to dinner, and spending time with mutual friends and each other’s families.

What makes the friendship special?
Ball: “He inspires me every time I see him. He lifts up people around him, his personality obviously, but also he cares about people. He gives back.”

Cason: “Every time I’m around her I feel the genuine love and care. She really cares. Sometimes you don’t feel that way around people. And my family loves her too.”

Best part of being in an age-gap friendship?
Ball: “I want to stay relevant for every day of my life. He helps me do that. And it’s not just the age difference. He is a different color than I am, a different culture. I love understanding that better. I can’t say I understand it totally but hopefully it makes me communicate better with everyone as a result of that.”

Cason: “For me — especially where I’ve been, what I’ve done — I feel safe with her. I like to stay as private as I can because everything I’ve done has been in the public. And I just feel safe. That’s very important.”

Flora Grewe, 4 1/2, hands her friend Mary Ota, 105, a handful of flowers in Carpinteria.

(Christina House / Los Angeles Times)

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Flora Grewe, 4 ½, student. Mary Ota, 105, retired medical office worker

How did you meet?
Ota: “Flora and her family lived at the end of the street where I used to go for a walk. I would sit on my walker and rest before turning around and she would come and bring me flowers. Then she started coming over and we just became friends. Now we get together a lot.”

Favorite activities:
Doing puzzles, getting matching manicures, giving presents.

What makes the friendship special?
Ota: “She is a sweet little girl, always smiling and just adorable. At first she was quite shy, but what was adorable is she would write notes and bring them to me. She would always smile when she brought me things, and even if they were just weeds, I would put them in water.”

Grewe: “I don’t even know! I just like her!”

Best part of being in an age-gap friendship?
Ota: “A friend like Flora keeps things lively. Young people are so full of life. And connecting with young people makes you recall when you were young and your children were young.”

Grewe: “She let me have two cupcakes at her birthday party. She’s nice.”

Patricia Smith, 74, and Adam Fowler, 43, sit outside Patricia’s apartment.

(Zoe Cranfill / Los Angeles Times)

patricia smith 73, retired faculty support at UCLA, yoga teacher. Adam Fowler, 43, consultant

How did you meet?
Fowler: “I took a position in Global Economics and Management at UCLA while I was applying to PhD programs. The first day the person I was replacing warned me about the woman down the hall. I hadn’t been in Los Angeles terribly long and I was like, ‘Oh, God, I hope this isn’t a nightmare.’ But we just hit it off.”

smith: “He endeared me to him with the ‘Yes, ma’am.’ It reminded me of the way I was brought up. And his Southern accent was the cutest thing in the world.”

Favorite activities:
Picnics at the Hollywood Bowl, movie nights at Hollywood Forever Cemetery, talking on the phone, fixing up smith’s apartment.

What makes the friendship special?
Fowler: “She made it comfortable to grow as a human. I was from the boonies of Arkansas, trying to figure out who I was in terms of coming out as gay, pursuing a PhD from a family where I was already the first generation of college students, and this was a person who was so secure in who she was and kind and generous.”

smith: “He was always so freaking smart, but he was smart without being arrogant. That was one of the more endearing qualities I recognized in him right away.”

Best part of being in an age- gap friendship?
smith: “He helps me to stay young. He turns me onto stuff. When I don’t know what’s going on, I just call him and he sets me straight. He helps me to pay attention — not to mention that he does [stuff] for me. That’s priceless.”

Fowler: “It’s such a source of context and wisdom. Whenever you get spun up on something small in your own life, patricia can either help you laugh about it or put it in some broader context. And just everything she’s done, moving here from Chicago, things she’s been through, all of that is so very interesting. I’d say it’s the resilience for me.”

Marlo Wamsganz, left, 54, and Norma Hench, right, 83, have been friends for years. The pair like to swap books, plant clippings, hike and visit botanic gardens.

(Dania Maxwell / Los Angeles Times)

Marlo Wamsganz, 54, designer. Norma Hench, 83, retired teacher

How did you meet?
Wamsganz: “We were both living in Vermont and I was dating her partner Glenn’s son. The first time we met we were already walking around her gardens. Then I moved on from that relationship and Glenn passed away. We lost touch, not because we didn’t love each other, but because life goes on. “

Hench: “It took me a full year to get my act together after Glenn died and move to L.A. where my son lives. I flew from Vermont to JFK and, lo and behold, there’s Marlo!”

Wamsganz: “We were both relocating to L.A. and when we got on the plane I believe we were in the same row. I thought, ‘This is wild.’ ”

Favorite activities:
Visiting botanic gardens, trying new foods, hiking in Malibu, visiting museums and swapping books.

What makes the friendship special?
Wamsganz: “Norma loves to learn new things, she’s up for anything, she’ll taste anything, and she also likes to dig deep into things. I love how positive she is and she speaks her mind. She’s very fair and believes in rights for all people. And she’s a great conversationalist.”

Hench: “I want to tell a story: We were crossing Ventura Boulevard — this big multi lane street, and right in the middle of the crosswalk there was a praying mantis. And without missing a beat, didn’t Marlo reach down and pick up this praying mantis and carry it with her across to the other side of the street and put it on the lawn? Now, doesn’t that speak volumes?”

Best part of being in an age-gap friendship?
Hench: “I never think about an age difference. I’m not even aware of that. Maybe I’m in denial.”

Wamsganz: “I don’t either. Although I do ask her some things. Like, how long do hot flashes go on?”

Friends Peggy Cheng, 40, left, and Karen Lektzian, 64, shop at the Santa Monica Farmer’s Market.

(Christina House / Los Angeles Times)

Peggy Cheng, 40, entrepreneur. Karen Lektzian, 64, retired IT consultant

How did you meet?
Cheng: “Her master toilet flooded my unit, and it was easier to go through my unit to fix it. I was working really long hours at that time, so I was just like, ‘Yup! OK! Bye!’ She was like, ‘Can I get you any gift cards or a dinner?’ and I was just like, ‘No! I don’t really expect to interact with you.’ ”

Lektzian: “The remediation took three weeks, and over the course of those three weeks we had quite a few interactions, so we got to know each other a little bit. I invited her to dinner and with the proximity we started to run into each other more often and it was so easy to just say, ‘Want to pop up for a drink? Or, do you want to cook dinner tonight?’ ”

Favorite activities?
Traveling, cooking, eating out, running errands.

What makes the friendship special?
Lektzian: “We just have so much fun together. It doesn’t matter what we’re doing. And we have so many common interests. It’s just so natural. Life is more fun with her.”

Cheng: “I like that I can share everything with her. She’s one of the few friends who knows every facet of my life. I can go to her for advice and if it’s serious she will just switch into that mode and then immediately we will have the giggles.”

What is the best part of being in an age-gap friendship?
Lektzian: “I don’t really notice when I’m with my friends my own age versus Peggy.”

Cheng: “I don’t feel it either. She’s equally energetic and way more fit than I am!”