A group of Sesame Street-ish puppets are huddled on the windowsill of John Oliver’s office in Manhattan’s Hell’s Kitchen, their orange and green yarn-hair blowing heroically in gusts from the air conditioner. So Oliver can’t help laughing as he ponders whether his HBO show, Last Week Tonight With John Oliver, has turned more serious than he expected, with exhaustive reports on thorny issues – payday loans, the death penalty, alleged FIFA corruption – that sometimes seem to pack more investigative heat than much of the non-comedic news media.
“It’s hard to answer that question when there are four puppets up there,” says Oliver, who spent seven and a half years as a Daily Show correspondent. “I think at the end of the day, no. It’s been really fun tackling some really serious, extremely complicated stories. But then there is a lot of stupidity in it. If we’ve gone hard one way, like if we’ve done a piece that includes looking at prison rape and prison conditions, we’ll try and end that with Muppets.”
In interviews for his first Rolling Stone cover story, Oliver and his friends and colleagues dug deep into his life and work, along with the behind-the-scenes world of Last Week Tonight and The Daily Show With Jon Stewart. Here’s the best of what didn’t make the print edition:
John Oliver was just about the only person who wasn’t sure he could handle his guest-anchoring stint on The Daily Show last summer.
“John was very nervous,” says Last Week Tonight showrunner Tim Carvell, who was The Daily Show’s head writer until last year. “Like, more nervous than you would think someone would be. But none of us really were. In the discussion we had early on about who would host in Jon’s absence, there was no question that Oliver was the best choice to do it. I think the only person who doubted that was Oliver. There was a fear that we would get rotating guest hosts or something like that, and it was like, ‘no, you want somebody that knows the show from the bottom up.'”
“I trailed Jon pretty directly, for a couple of weeks before he left,” adds Oliver. “And then, otherwise, I just copied him. I loved every second of The Daily Show, and I really did not want to leave. It was really, really hard to leave.”
Oliver has always been a workaholic.
At The Daily Show, he used to come back from long-distance shoots at three in the morning, and then turn up early the next day to write the show – not to mention happily spend nights and weekends editing his pieces. “I prefer to think of it as he has a wonderful work ethic,” says Jon Stewart. “I prefer to think of it in the positive. John and I share that two-dimensional ability to focus on the thing we’re probably most happy and comfortable doing, which is working. He and are similar in that sense – we’re not that comfortable socially. When I was younger, I bartended rather than going out. So then I could say, ‘Yeah, I was there,’ but I was working. And I think in a similar sense, he enjoys the craft of it. Certain people are molars. He’s a molar, you know? He likes to get in there and just chew. And then regurgitate it. Maybe into a baby bird’s mouth. That’s how we work.”
There had been talk of expanding Last Week Tonight beyond Sunday nights, but that’s unlikely for now.
Says HBO programming chief Mike Lombardo, “If John came to me tomorrow and said, ‘I think we’re ready to do more than once a week,’ I’m with him. I also know how rare it is to get something that feels like it’s working, and I don’t take that for granted.”
“HBO is kind of open to everything, it seems, until the big pillow in the sky comes down and is pressed over our face,” Oliver adds. “They’ve been unremittingly supportive in their silence. We have an option to do 60-minute specials of the show, if we want. You know, 60-minute one-offs. I think we need to get good enough at making 30 minutes before we can think about doing 60. This show is exhausting to produce in 30-minute form, and it’s intense enough to watch that I’m worried that at 60 minutes, it could be exhausting to watch. It’s not unlike how you look at 30 Rock and you realize there’s a joke in almost every line. They just don’t hang around. Or Arrested Development, where it’s just packed.”