John Oliver on the Luxurious 'Freedom' of HBO, His Complicated Relationship With NYC

This story first appeared in the May 2 issue of The Hollywood Reporter magazine.

John Oliver is sitting behind his large wooden desk in his barely furnished office on the eighth floor of 555 West 57th St., one floor below CBS' 60 Minutes. There are no books on the metal-and-wood bookcase behind him. The TV is switched to CNN, on mute. It is mid-March, and several rooms on the floor are in various stages of construction; in one, heaps of plaster and drywall litter the floor. Oliver and his executive producer, Tim Carvell, still are hiring writers and producers for Oliver's new HBO program, Last Week Tonight. And true to his self-deprecating Britishness, he's a little uncomfortable going from hardworking team player to boss.

"As a comedian, your whole life you're kind of trained to avoid authority," he explains. "So to suddenly be the authority is a very, very bizarre situation."

Dressed in all-weather boots, khakis and a black-and-blue checked flannel shirt, he tells me that managerial cliches are starting to come out of his mouth: "I'm talking about trying to get the departments to synchronize. I sound like everything I've come to hate."

For all his self-deprecation, Oliver, who turns 37 on April 23, also shows why HBO has so much confidence in him. He will do whatever it takes. Later that week, on a clear, cold Friday, one of the last days of the winter of the polar vortex, Oliver gamely will indulge us as we subject him to a rather unorthodox photo shoot concept. Standing stiffly on the roof of the CBS Broadcast Center, with the wind howling off the Hudson River, he watches as a prop guy hoists a bright orange, five-gallon bucket filled with water -- warm water -- over his head.

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"Ready?" asks the prop guy skeptically.

Oliver removes his glasses. "Go, top to bottom. Do it!"

The water washes over Oliver and lands with a splash at his feet. "There aren't many dry bits," he observes as he squishes over to a platform against the southern edge of the roof. An assistant hands him an umbrella while another splashes more water on his jacket. The photographer begins to snap away. "Are you OK, John?" he asks.

"Great," laughs Oliver, stifling a shiver. "Commit to the bit!"

Oliver has been committing to the bit, so to speak, almost his entire life, or since he realized sometime in secondary school that becoming a professional footballer was hopeless. As a child, he would lie awake at night listening to recordings of Richard Pryor. "I knew most Richard Pryor albums by heart by the time I was 15," he says. "You have not heard Richard Pryor stand-up until you've heard it through the voice of a 15-year-old white, British boy."

By the time he was recruited in 2006 to become one of Jon Stewart's supporting players on Comedy Central's The Daily Show, he already had spent several years honing his act on the London student circuit and in dodgy basement venues. Now, Oliver is in the thick of launching his own show. Premiering April 27, Last Week Tonight will air at 11 p.m. Sundays on HBO. The half-hour show, which will be shot in front of a studio audience in the CBS studio previously occupied by Bethenny Frankel's doomed daytime talk show, will look familiar to Daily Show viewers in its structure -- the clip-driven A-block, field pieces, interviews. But the weekly format will mean that Oliver and his producers and writers will need to approach topics differently than his former colleagues on The Daily Show or The Colbert Report. Oliver mentions the recent General Motors recall as the type of story that demands greater attention.

Click on the photo to view more portraits of the comedian.

"It's pretty incredible considering they may have killed 300 people," says Oliver. "It's as bad as it gets, and yet there's been a slightly peculiar lack of outrage."

In his seven years on The Daily Show, Oliver has developed a nuanced understanding of America's political and social foibles and exposed them in brilliantly crafted field pieces on everything from gun control to the bankruptcy of Detroit. He has a gift for guilelessly stringing along interview subjects until they make the joke for him.

"He's improvising with someone who does not realize they are in a scene," explains Stewart. "The law of improvisation is, 'Yes, and …' But to get to a point that is going to crystallize your idea is not easy. He's always had sort of a strange affinity for it. I've seen people improve on it, start to understand it, start to see the field a little better. But I've rarely seen anybody do it as well as he does."

A perfect example of Oliver's depth of field was a three-part gun control piece that aired on The Daily Show in April 2013, several months after the massacre at Sandy Hook Elementary School. Oliver traveled to Australia to show that gun control laws actually can work and got an aide to Senate Majority Leader Harry Reid to admit that success in Washington is measured not by laws passed or constituents served but by whether a politician can keep getting re-elected. The aide thanked Oliver after the piece ran.

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"He's able to make sure that person continues on their path while guiding them into a small room where he can smack them around for a while, in a very graceful way," adds Rory Albanese, the longtime executive producer on The Daily Show. "And if they do catch on, he still knows how to handle that."

Oliver's run on The Daily Show ended in December, four months after a successful summer stint filling in for Stewart when he was off directing his first movie. Although the 12-week gig did not exactly make him a household name, it showcased Oliver's big-league potential.

"I said to him, 'Once you do this, once you fly the plane, you cannot go back,' " recalls Stewart. The two men had been talking about what Oliver would do next before Stewart left last June. "He's not the kind of person to shrink from a challenge. But I think it was just unnerving."

The offers flooded in. "There was a slightly weird amount of interest," allows Oliver. Executives at CBS -- considering their late-night options in anticipation of David Letterman's retirement, which was announced April 3 -- talked to Oliver about the 12:30 slot currently occupied by Craig Ferguson, whose contract comes up this year. And it began to dawn on Oliver that he actually had worked himself out of the best job he'd ever had.

"I just, I couldn't even comprehend it," he stammers. "I went, 'No, what are you talking about? No, no, no, no, no!' It was terrifying. That was my dream job."

If he had to leave The Daily Show, HBO's offer -- a two-year deal with an option for more, complete creative freedom (no obligatory interviews with celebrities promoting their latest film or TV project) and none of the ratings pressure (or potential for disgruntlement on the part of sponsors) inherent to commercial television -- was hard to match.

"You can have real freedom, and not just the blood or boobs," says Oliver. For instance, a bit tearing into GM's slow response to ignition problems led the first test show March 30. "To do a very aggressive piece on [General Motors] before a congressional investigation, that's potentially a problem on commercial TV. I don't think it would be outlawed. But I think there would be a sense of, 'Do you have to do this?' "

Oliver's departure also is a blow to Stewart, who has seen several proteges depart, including Ed Helms, Steve Carell and Stephen Colbert. But the timing was impossible to manage. Until the announcement April 10 that Colbert would succeed Letterman, opening up the 11:30 p.m. slot following The Daily Show, Comedy Central did not have the real estate to accommodate Oliver.

Click the photo to see John Oliver's 5 comedic influences.

"Obviously, look, my preference would have been that I have him forever," admits Stewart. "But I also know that's not how it works here. We get these really talented people for a certain time until other people recognize that and go, 'Hey, why don't I pay him more and let him do it over here?' "

Nevertheless, Stewart advised Oliver to take the offer: "I said, 'You've got to do that. That's too juicy a meal to pass up.' "

Before Oliver began filling in for Stewart, HBO programming president Michael Lombardo only had a vague notion of who Oliver was. "When he took over, everyone including myself went, 'Well, I don't know, that's a tough seat to fill ...' " recalls Lombardo. "And I thought he hit it out of the park. He made it very much his own, very quickly. I hate to say it, I missed him when Jon came back."

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Lombardo wasn't looking for another comedian: The network has a well-established stand-up tradition (Chris Rock, Louis C.K., John Leguizamo), while Bill Maher's Friday program Real Time has been on for nearly 10 years. But Oliver's sensibility just felt right for HBO.

"He has a very inviting way of having us all take a look at issues around us with amusement, with sadness, with irony," says Lombardo. "But there's no cynicism or judgment in it. His observations are always really acute and heartfelt."

They have talked about expanding the show to an hour or having it on more than once a week as well as giving Oliver a new home for his stand-up -- once Oliver gets his feet under him. He also will be producing shortform digital content tailored for the viral universe. The show released two videos March 20 on YouTube that parody the Republican National Committee's bizarrely tone-deaf "Create Your American Dream" spots.

"There's just no way he's going to fail on HBO," adds Lombardo. "It's not going to be about the numbers; it's going to be about doing the best show he can do. We're not going to look at him and go, 'Oh my God, John, you dropped 50 percent from your lead-in. You need to bring in Lindsay Lohan.' It's just not going to happen here. We're committed."

Oliver had not even been to America before he was summoned in 2006 for a Daily Show audition, apparently on the recommendation of Ricky Gervais, a fellow Brit who was familiar with Oliver's career in the U.K. The show flew him coach from London, and he got the job a few weeks later -- arriving on a Sunday in July and making his first appearance the very next day in a bit about President George W. Bush's open-mic gaffe at a Group of Eight summit in St. Petersburg, Russia. When Stewart walked onstage to wild applause from the studio audience, recalls Oliver, "I remember my legs going a little bit wobbly and then thinking: 'What the f--- are you doing? You're about to get found out in a big way.' "

And then it got weirder. In the section of the audience nearest the greenscreen, where Oliver was standing to deliver his bit, sat J.K. Rowling. The Harry Potter author was in New York for a reading.

"She's just sitting there in the front row. And then she came round afterwards to say hello to Jon, and there is basically the modern queen of England. And so I kind of babbled something at her about it being my first day. And she said, 'Well done,' and gave me a hug. It was a very bizarre first day."

His first field piece for The Daily Show showed Oliver's ability to find comedy in difficult subjects as well as his intuitive gift for going wherever the material takes him. With the Iraq War raging, he traveled to upstate New York to join Civil War re-enactors in an attempt to understand America's love affair with bloodlust. Dressed in a Union uniform and carrying a musket, he charged through a grassy meadow only to fall squarely on his face -- breaking his nose. The piece then turned into a Civil War injury re-enactment, with Oliver's producer pretending to drive him to a local emergency room and Oliver in the backseat, rag to gushing proboscis. (In actuality, Oliver did not go to a hospital until he got back to the city.) "My thoughts turned to things I hold most dear," intones Oliver in voiceover. "I was hungry before, I had a sandwich. It wasn't a great sandwich. Tim, the producer, didn't provide the sandwich that perhaps the situation demanded …"

Recalls Albanese, "We send this guy out for the first time, he knows no one in America, he's living alone in a tiny little apartment on Perry Street, his family's overseas, and he comes back with a busted nose."

When I ask Oliver about this episode, he bursts into laughter: "I have a nose that is long enough that my nose breaks my fall for my face." The field producer sent the footage back to The Daily Show so the editors could begin to cut the piece. "And by the time I got back to the office later that day," he recalls, "you could hear laughter echoing around the halls as people watched it over and over."

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Oliver can laugh at himself, but his interests have a genuinely serious side, too. Oliver's wife, Kate Norley, served as a combat medic in Iraq. They met when Norley hid Oliver from security at the Republican National Convention in 2008 in St. Paul, Minn. She was there on behalf of the advocacy group Vets for Freedom, and Oliver had sneaked onto the second floor of the Xcel Energy Center, where he was not authorized to go. At the time, he still was in America on a work visa -- he has a green card now -- and if he had been arrested, he conceivably could have been deported. They married in 2011. "The end result is romantic; at the time, it just felt harrowing," he says.

Immediately after his summer stretch in Stewart's seat, Oliver went with Norley, Albanese and Daily Show staffers Adam Lowitt and Elliott Kalan to Afghanistan as part of the USO Tour. They slept in the barracks, ate with the troops and performed at more than half a dozen forward operating bases. Which required a somewhat different approach to comedy.

"It is pretty absurd being on a rocky base in the middle of the Hindu Kush mountains. It is incredibly serious. But it's also pretty absurd," explains Oliver. "The whole of their day is incredibly dramatic and serious and boring. And so you're just looking to try to give them a taste of home and a taste of nonconformity. You do anything to make them laugh."

Including, apparently, zapping yourself in the leg with a taser gun, which is what Oliver did during one performance -- to uproarious cheers from the troops. Asked whether it hurt, a bemused grin crosses his face. "It was incredibly painful!"

He and his wife live within walking distance of his studio, and after more than seven years in New York, Oliver has developed a pronounced love-hate relationship with the city. "There's something about living here that is inherently ridiculous because it costs too much, it's not clean, it's not pleasant and you just get addicted to it. Eight million people have made a bad choice. And I'm one of those 8 million. I don't think New Yorkers are angry with each other as they are so much angry with themselves. It's a huge character flaw."

Oliver found his comedic voice at the Footlights, a famed drama club at Cambridge (where he was studying English) that turned out a who's who of British satirists including John Cleese, Graham Chapman and Peter Cook, all of whom Oliver counts as influences. "It's where I learned how to fail," he says. He began writing with classmate and fellow comedian Richard Ayoade, "probably with more tenacity than either of us were studying," he recalls. And after graduating in 1998, they moved into "a terrible flat in south London with blood in the stairwell." While he was working to establish himself as a comedian and writer, he took odd jobs; he shoveled oats in a factory and answered the phones for a guy who fenced stolen kitchen equipment. "The phone would ring, and a guy would say, 'Is Jim there?' And I said, 'I've been told to say he isn't.' And he said, 'All right. I need you to take down a message. Tell him, if he doesn't call me back by this evening, I'm going to come down there and I'm going to cut his throat. Now, did you write that down? Read it back to me,' " recalls Oliver, laughing. "I thought, 'I'm out of my depth here.' " On another occasion, Jim sent him across London in a cab with about $8,000 and a knife. "I said to him, 'If anyone tries to rob me, I am giving him the money and the knife,' " says Oliver. "I think he just found me amusing to have around. Our lives were not supposed to intersect in any way."

Growing up in Bedford, England -- one of the formerly proud industrial towns north of London -- the eldest of four children of schoolteachers, Oliver attended what he describes as a "rough" high school.

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"I grew up watching my parents deal with the consequences of what the Thatcher government did to public education in England," says Oliver. "I think it's hard to be apathetic when you're raised under Margaret Thatcher; you're going to get pushed one way or the other."

His class rage kicked in at Cambridge when he found he did not feel entirely comfortable around the upper end of the British class system, and he channeled that into writing. He landed gigs at the Edinburgh Festival Fringe and small writing jobs on BBC radio. He performed often with British comedian Andy Zaltzman, with whom he has done "The Bugle" podcast since 2007. Zaltzman recalls one gig in summer 2001, when Zaltzman made his solo debut at Edinburgh in "Andy Zaltzman and the Dog of Doom" and Oliver was the offstage voice of the dog.

"He's always been a very natural comic performer," observes Zaltzman. "And with stand-up, that gives you a great head start. And then if you can ally the writing skills to that, then that becomes a very potent combination."

In 2003, Armando Iannucci (the Scottish writer and director of In the Loop) hired Oliver to write for Gash, a weeklong radio program that coincided with local U.K. elections. For comedians who write their own material, radio in the U.K. often is a point of entry. And on Gash, Oliver proved himself a sharp cultural critic who could churn out copy quickly. "You can't write lazily on the radio," notes Iannucci. "You learn to write with focus and make each word count. And John was fantastic at that. I was the host and John was my kind of sidekick, and he would throw out these comments and observations. I instantly relaxed because I knew I was with someone who was completely comfortable in the topical world of comedy."

Oliver considers Gash a breakthrough -- the inflection point in his career when he made enough money for real cheese and orange juice with pulp. High-quality juice remains a symbol of success for Oliver. "Just this morning I'm looking at this nice orange juice in the fridge from Citarella," he muses. "And I thought, 'Wow, look at that.' "

Oliver is anything but complacent. He knows that stand-up is a capricious art form. No matter how famous you become, the crushing reality is, you often are only as good as your last joke. "That's part of the rite of passage of stand-up," says Zaltzman. "You could be five miles away from where you live, and it's about as lonely as you can get in a room full of hate."

That doesn't mean there isn't something to learn from the disastrous gigs. "You learn what you're willing to stand behind, and you learn what needs to be better," says Oliver.

When comedians become popular enough to land regular television jobs, they often, unconsciously or not, suppress their instinct toward combativeness and uncomfortable truths in order to get along -- with their guest, network standards and practices, viewers in the heartland. Oliver is determined not to fall into that trap. And at least some of those concerns are ameliorated by being on HBO, where there are no sponsors to rankle. But his approach is to look past the inviting tabloid fodder that constantly presents itself (hello, Anthony Weiner) and search out the sad, perplexing or troubling story and turn it into comedy that illuminates. The Trayvon Martin verdict, which came down a month into Oliver's tenure at the helm of The Daily Show last summer, is an example. "That was not easy," he admits. "You start with these feelings of disgust and rage, and as the day goes on, you kind of get excited about, 'Oh, I think we're managing to say the complicated things we're wanting to say.' "

It's clear Oliver is not afraid to fall flat on his face -- literally. And in fact, he continues to seek out difficult challenges with a high chance of failure. When he's working out his material for stand-up specials, he tends to pick hard rooms like the Pittsburgh Improv.

"With friendly audiences, you can kind of get by on goodwill," he explains. "But it's hard to ascertain sometimes where the gaps are. So the Pittsburgh Improv has been very useful. I love it because they'll give you no momentum. Maybe you've had like a rolling five minutes of jokes; one thing doesn't work, the whole evening screeches to a halt. You have no goodwill in the bank. It's a joke-by-joke judgment."