Jon Stewart was done. Sixteen years behind the moderator's desk The Daily Show He was physically exhausted, creatively burned out, and eager to get reacquainted with his children. He left the show on a high note, with a star-studded finale episode that featured a live performance by Bruce Springsteen and a sarcastic dig from Hillary Clinton. There was even a book (by me) that detailed how Stewart transformed a silly, simple cable show into an influential political satire and how he had spawned a wealth of comedic talent, including Steve Carell, Samantha Bee, Ed Helms, Jessica Williams, John Oliver, And Stephen Colbert. With Stewart's departure in August 2015, his timing seemed perfect: handing over to his successor, Trevor Noah, included a presidential contest between Clinton and Donald Trump, a matchup ripe for comedy. Stewart could ride off into the sunset and the show and the country would be in good hands.

At least things were going well for Noah. Stewart, meanwhile, directed a film (starring Carell) whose release was dampened by the pandemic; He created a show for Apple TV+ that ended unfortunately. Outside of the film, however, Stewart had significant influence by getting Congress to fund health care for sick 9/11 first responders and for soldiers exposed to toxic burn pits. But 2023 ended with Comedy Central still searching for a successor to Noah and Stewart in general, and a high-stakes presidential election looming. Stewart returned to the Daily Show at my desk this February, but only on Monday evenings.

He wasted no time in making a splash in his first show, skewering the advanced age of Trump and the president in particular Joe Biden. Stewart also made a prediction: “The next nine months or so – and maybe longer, depending on the coup plan – are going to suck.” He wasn't wrong, as Sunday night's ugly Trump rally at Madison Square Garden was just the latest Low point. Paramount announced this week that Stewart will remain as Monday host through December 2025. On election night he will host a live show starting at 11 p.m. and lasting one hour. He hopes to stay awake the whole time. “Obviously I’ll be in the hyperbaric chamber for most of the day,” Stewart said. “Maybe I’ll pull out a murphy bed after half an hour.”

Jon Stewart: Hey, man, what's going on?

Vanity Fair: A lot. You sound like you're on the move.

Yes, I'm going to a gig. I'm on the way – because show business is a glamorous profession – on the way to Albany. So if I lose you, I'll be in the mountains for a bit. I like to go out every month or so and spend a weekend. And I like driving. So I'm doing Albany tonight, driving to Worcester tomorrow and then heading home.

We're talking about ten days before the election –

Is it 10? I didn't count. It wasn't really on my radar.

What is your primary feeling right now? Fear, terror, anger?

Yes, according to the sphinctometer I would say that I am almost hermetically sealed. It's very tense. I try not to let the daily rhythm of Twitter and cable news dominate my every waking moment. You know, I look at the opinion polls, the state polls and the swing state polls. But it's very hard, in a very neurotic way, not to check every tentpole of the election prediction.

That's another reason why it's healthy to be out and about.

I've said this, and many people have said it before me: When in doubt, go to Albany. It is your bridge over troubled waters.

The presidential race is incredibly close. The problem is clearly that you should have ousted Joe Biden sooner to give Kamala Harris more time to run a campaign.

So no matter what happens, can we still come back and leave this on my doorstep?

Naturally.

So that's me Jill Stone from Ralph Naders?

No, you nailed the issue of Biden's age.

When we came back, the whole idea was: Let's raise our flag for the 2024 election. What is it about the dynamics of race that concerns us most? That was the genesis of the bit. You never know if it's going to hit a nerve. But in reality it was more likely to capture people's angry mood when they said: Why would you say something like that?! What are you doing?! And our answer is always: We have only said what we see through our eyeholes and hear through our earholes. So we said it through our mouth holes.

And then you feel vindicated or depressed or what by Biden's disastrous debate performance?

Well, certainly depressed on a human level, not on a political level. This is a person who I have a lot of respect for and who has been very helpful and I really liked on some of the issues that I've been working on with some veterans groups. You know, he's like one of those guys in your town – you go in and have coffee and there's Frank sitting at the table; he only holds court. Biden is the mayor of every city who also happened to be president. It is not only related to political reality, but also to human reality, in the well-known sense that all our shows will be canceled at some point.

Over the last month or so, Harris has had a minor role in the episodes you host, while there has been a lot of material about Trump. Is this because she's boring or because he's particularly dangerous?