20 Things You Learn Hanging Out With John Oliver

From his teenage girl troubles to a near-fight with an Ali G impersonator, here's what didn't fit into his first Rolling Stone cover story

John Oliver reveals new details about the birth of 'Last Week Tonight' in interviews for his Rolling Stone cover story. Credit: Jesse Dittmar for The Washington Post via Getty Images

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."

The show had some alternate titles.
"I remember pitching Breaking News on a Weekly Basis as the title of the show, which became like a tagline on the first episode, but that just felt too long," says Carvell. "John was the one who came up with Last Week Tonight, which it was one of those things where we didn't know but then we kept circling back to it. There was John Oliver 180, but I don't think he wanted his name that prominent in the show, and also, it's a dumb Anderson Cooper 360 joke that will get old."

And in any case, the show's name is officially misleading.
"As long as we do something at the start that kind of tips the hat to the week that just happened, all bets are off after that," says Oliver. "We're leaning towards doing stories that maybe you missed in the last week, or stories that were not particularly timely to the week, but were relevant."

Unlike The Daily Show, Last Week Tonight hasn't spent much time mocking the ludicrousness of cable news – or even using its footage.
"That's the way it's fallen, so far," says Oliver. "It's impossible to avoid some stuff about cable news, when it's just so bad. But generally, we've been forced to look to other sources, because some of the stories we were looking at weren't really covered on cable news. So, the stuff that we've been using for stories has been more from Bloomberg, Al-Jazeera, BBC International or foreign news agencies like India Today. That's where we've been finding the stuff that we need to tell the story."

Oliver originally thought the show would be easier to produce than The Daily Show, which was wildly off.
"I was wrong about that," he says with a laugh. "Sometimes it feels like being hit by a very slow-moving train. Something that you can see in the distance and think, 'Oh, really, I should move. I should move and get out of the way of this imminent disaster. Oh, no, here it comes!'"

Oliver is a lifelong soccer fanatic, who never quite got over his dream of becoming a professional footballer.
"There's still part it that gets me," he says. "I went to Yankee Stadium last week to watch Liverpool play Man City. I got to go downstairs after the game, and I walked into the locker room, and I couldn't really handle it. I walked in, and it was the thing I'd dreamed of since I was a kid. And there were some of my utter heroes there, even though some of them are, like, 20 years old. And half of them are naked, which is weird for a start. If the phrase 'Never meet your hero' is true, 'Never meet your hero's penis' is probably even more true. I'm still coming to terms with the fact that half of Liverpool's team, I've now seen their junk. And I don't know if that is going to enhance or diminish my experience of them next season."

He'd listen to Richard Pryor records over and over as a kid.
"The images he created were so funny, and so raw and honest, that it bore repeat listening," Oliver says. "There's that cliché that people want to watch a band and hear the stuff they know, whereas with comedians, you say, 'Yeah, tell me something else. I know the stuff you've already done, tell me something new.' But there's an amazing Richard Pryor bit, where he talks about people coming to his shows and actually wanting his old stuff and mouthing along with what he's saying, and then getting angry with him when he changes a word. I think he has some bit where someone's shouting, 'You didn't do it like that on the record, motherfucker! Do it right!' What I loved about him was that it felt like music, because it felt like he could come back to it and it was all so perfectly written and performed that you could look forward to each bit that you knew was coming."

His teenage years had their rough spots.
Oliver played on various sports teams and studied the violin, but never felt like he quite fit in anywhere. "It's just shit, growing up," he says. "Being a teenager is just not an easy thing to go through. You just want to say to someone who's a teenager now, 'If you get out the other side, I'm not even saying that it's going to be better, but it's going to be over. The world will expand, at least.' You just don't feel like you're doing anything right. You're not good enough at anything. You're not good enough at interacting with other human beings. You physically don't make sense. I think that's why I find it so inexplicable when you see really confident, well-put-together kids. You just think, "What?" Occasionally I'll meet 16-year-old kids that give you a really firm handshake and look you in the eye, and you think, "You're more confident than I am now! How is that possible?"

Women were a challenge, early on.
"I never wondered whether I might be gay," he says. "I did wonder if I would ever be attractive to women. I was very clear about the fact that I liked girls, and that that was, at the moment, a one-way admiration. I played on all the sports teams. That still didn't do it. Membership is not enough. You could see girls thinking, "Yeah, I see you on the field. That's great. I just don't think of you that way."

His early stand-up years in the U.K. were some of "the happiest times" he's ever had.
"It's undeniably physically grim from the outside," he says, "if you're traveling to gigs constantly where you're getting paid nothing, you're sleeping in shitty hotels or sleeping on night trains or night buses on the way home. And yet there is nothing more exciting than feeling like you're getting better at something, and each time you reach a cap, finding a way to break through it. When I started off, you just want to get that laugh."

Oliver has more or less modeled everything he does on his mentor, Jon Stewart.
 "I guess I'm as much as a disciple of his as it's possible to be," he says. "The fact that there is nothing so far that he has not taught me. So I feel like he is my DNA."

He isn't particularly interested in fame.
"I don't really want to be famous," he says. "I understand that there are things that need to happen for the show, like have a stupid billboard over the Gristedes sign. But the whole world of it is not something that I find appealing in any way. I like doing this. I like working, doing the thing, and then leaving. I like ringing the buzzer, and then running away, rather than sticking around. I don't do great at awards shows. I've been to the Emmys with The Daily Show, and it's fine, and it's fun. But a little goes a long way of that, with me. It's fun to see the cast of Mad Men in the flesh, but you're looking at them as an outsider, going, "Wow. Look at them, moving their arms around. One of them's eating!"

He doesn't think he could ever host the Washington Correspondents' Dinner.
"I've annoyed too many people in the news world," he says. "That is a room with a lot of passive aggression in it."

Stewart and Oliver are convinced there's plenty of room for both of their shows.
"Oh, of course," says Oliver. "When your comedic perspective is different, then of course there's room. Otherwise there would only be one state-run comedy news organization.  Like, 'Here is your laugh for the evening.'"

There's no room for writers' block in his world.
"None whatsoever," says Oliver. "You have to hope that panic knocks that writers' block down, otherwise, again, you're staring into a camera with dry mouth, double-swallowing. There's just no time."

He's not sure Last Week Tonight is quite funny enough to get people over the bleakness of The Leftovers, which preceded it on Sunday nights.
"I watched the finale on Monday, and yeah, I mean, holy shit, that is gut-wrenchingly bleak," says Oliver, laughing. "It's just amazing that something like that is available on television. And I get to the end of it, and I loved it, and ... yeah, you're just emotionally wrung out. And the credits run, and I had completely forgotten. So then they said, "Coming up, Last Week Tonight. And I go, "Fuck, no!"  But that is a hard, hard turn. [Laughs] 'What is life? Is it pointless, fundamentally? Hey, who's ready to laugh?' I don't know. ‘I'm going to bed, curl up in a windowless room.'" 

Oliver hates the idea of people starting to see him as America's comedic conscience.
"If that's true, the canary in the coal mine is dead," he says. "It's way too much responsibility, and I have no interest in accepting that. Yeah, you have to look elsewhere. You just have to!"

Oliver once nearly got into a fistfight with an Ali G impersonator.
Comedian Andy Zaltzman, who would later become Oliver's partner on the cult-favorite the Bugle podcast, recalls a dramatic moment at a student-union gig years back. "This guy did a short spot at the student gig just impersonating Ali G," says Zaltzman. "He was basically using someone else's jokes, and this guy totally died on his ass, and he was trying to promote some other gig there. And then John went on and said, "Obviously don't go see that. That's just a man using someone else's jokes." So John was confronted by this man who was about 5'6" in full yellow Ali G kit and jewelry, threatening him with an extremely violent altercation. He says to John, 'Have you never died at a gig?' And John said, 'Yes I have, but I've done it as myself, using my own work.' This was broken up before it ended in a fight, but it was a fairly comic sight, seeing John face-to-face with a short man dressed as Ali G who was in a state of considerable anger."