Lisa Rogak - Angry Optimist

Until March of 2013, that is, when he announced that he’d be leaving for three months to direct the movie which now bore the title Rosewater. Though he had finished the script a couple of years earlier, he had had to wait on the financing; Stewart knew that once he got the go-ahead, he had to move fast.

In the first few years that Stewart was hosting The Daily Show, whenever he couldn’t be on the set, one of the correspondents ended up sitting in the anchor’s chair. Most of the time, that substitute host was Colbert—though Steve Carell also occasionally subbed for Stewart—and his success at the job inevitably led to The Colbert Report . After Colbert left, Stewart had changed course and decided to put the show on hiatus whenever he had to be away, usually just a week at a time, though the longest previous hiatus of just over two months occurred during the writers’ strike of 2007–2008.

But an absence of twelve weeks from the airwaves was another matter entirely, and it was clear that Comedy Central executives—not to mention viewers—wouldn’t stand for it. And so Stewart decided to appoint the Show ’s “senior British correspondent” John Oliver as guest host for the entire time. Four weeks would consist of reruns, while Oliver would end up hosting for eight weeks in all.

Stewart was eager to pursue new opportunities away from The Daily Show, but it was also clear he needed a break. Some of his previous supporters now had issues with him, and could point out recent mistakes and missteps he’d made, in their eyes. For one, they started to criticize his knowledge of how government and policy works, and they were becoming impatient with what they viewed as his ignorance.

“Stewart seems weirdly unaware that there’s more to fiscal policy than balancing the budget,” said New York Times columnist Paul Krugman. “But in this case he also seems unaware that the president can’t just decide unilaterally to spend 40 percent less; he’s constitutionally obliged to spend what the law tells him to spend.”

Jonathan Chait, a writer with New York magazine, piled on as well. “One of the habits [Stewart] has is to want to be bipartisan, but sometimes he misunderstands the way he needs to do that,” said Chait. “Basically, you’ll have Republicans in Congress do something objectionable, and the Democrats won’t agree to it. Then he’ll blame it on ‘Congress.’ It’s not fair to criticize both parties in Congress when one side is doing something objectionable.”

So when June arrived and he hosted his last show before the hiatus, it was a good time to get out of Dodge.

But that didn’t mean stepping away from the desk would be easy for him.

When it came time to leave, Stewart was visibly nervous about his first attempt at directing a film. “I am a television person who is accustomed to having a thought at ten A.M. and having it out there at six thirty P.M. and then moving on, so this is a little scary,” he admitted. “But one of the reasons we are in this business is to challenge ourselves.

“It’s something I haven’t done before, so I’m certainly coming from a place where I feel a lot more confident, or at least routinized,” he said. “I’m moving into this area [that’s new to me], so I thought the first day it might be nice to just sit in the chair and read Filmmaking for Dummies just to let them know that they are being led by an idiot boy. But I’m looking forward to it. It’s a real good story.”

Besides, as he had said many times before, it was in his makeup to be restless. “I like doing different things by nature,” he admitted.

But in a way, the only thing that would change on the show would be the host. The production of The Daily Show had, by this time, become a well-oiled machine with not much left to chance. Perhaps that had been part of the problem the critics had noticed: it had become way too predictable.

“Everything will fundamentally stay the same, in terms of the way that the show runs,” said Oliver. “Jon built it to operate in a certain process, so that process really has to stay. It’s like a NASCAR driver giving keys to his car to a member of his pit crew. I fundamentally understand how the engine works—I just never have driven it that fast before.”

Nevertheless, Comedy Central executives were understandably nervous. “[Taking time off] is something that he’s been interested in for a while, so we worked out a way to accommodate it,” said Kent Alterman, programming chief at Comedy Central. “We’re interested in him being fulfilled and happy here, so nobody ever told him, ‘You can’t do this,’ and we know he takes the show very seriously. There was a shared feeling between Jon and us that John Oliver made the most sense to fill in.”

“I’m fortunate to have the type of people who have been producing it,” said Stewart. “We’ve been there almost fifteen years, and Oliver is top-notch. He’s a guy who has all the tools. He’s so ready to do this, I don’t think they’ll miss a beat. If anything, he’ll bring a nice British sophistication. It will be like Upstairs, Downstairs where everybody has been downstairs for a long time and now we’re going to get to go upstairs.”

In the seven years that Oliver had been a correspondent on the show, he had risen to the top of the heap, just as Colbert had done years earlier. And like Stewart, he was a news junkie. He kept his TV on at home all the time, though in order to keep a happy home life with his wife, Kate Norley, a veteran of the Iraq War, he learned to turn it off at night.

Oliver was excited but equally nervous about his hosting debut. “I’m looking forward to it in the way someone looks forward to a bungee jump,” said Oliver. “I know it will be a fun and exciting experience, but I’m just not a hundred percent sure I should be doing it. But it’s a real honor to be able to do this for him, however misplaced that trust.”

He was also uncertain about how the set of the Show would feel without Stewart. “He’s a large part of our lives here, and the prospect of not having him around is a dislocating feeling,” Oliver admitted.

At the same time, Oliver had spent enough time on the set that he was fully aware of how the show operated on a day-to-day basis. “Jon has always told us [that] you want to make sure that the spine of the argument is in shape,” he said. “You can write jokes at any point of the day. Jokes are not that hard to write, or they shouldn’t be when it is literally your job. It’s harder to shift the point of view of a headline later in the day. That’s the kind of thing you need to keep an eye on early. You’d think you’d come in early in the day and go, ‘What jokes should we tell?’ And that’s not always the case.”

“This show is such a sausage factory, that you are only concerned with the next day,” Oliver added. “I find it hard in my general life to think further than the week ahead. So I’ve not really taken any big-picture thought about it, other than survival. But I’ve never had a regular job till I moved here. So I still can’t imagine not working here. It really is just a process of trying to get each show on.”

On June 10, Oliver assumed hosting duties, and once he settled into Stewart’s seat, he let loose: “Welcome to The Daily Show, ” he began. “I am John Oliver and let’s all just acknowledge for a moment that this is weird. This looks weird. It feels weird. It even sounds weird.”

Over the next three months, both he and the critics were surprised at how well he did. From the first week that Oliver filled in as guest host, it was clear Stewart had made the right choice. Critics raved about The Daily Show, something they hadn’t done for a while. And some made no secret of the fact that they actually preferred Oliver over Stewart as the mainstay.