HBO's incendiary 'Last Week Tonight' host (and recently sworn-in American) returns with plenty to say about Trump's 2020 campaign, Harry and Meghan, his awkward run-in with an AT&T exec ("We sized each other up"), and the secrets behind his Emmy-winning brand of "aggressively-researched comedy."

On Friday Dec. 13, 2019, at the age of 42, John Oliver became a U.S. citizen. He can vote. He can serve on a jury. He can get arrested — without fear of being deported.

Since 2006, when he first came to the U.S. to work as "senior British correspondent" on The Daily Show, Oliver has lived with a pulsating anxiety that his life could be upended at any moment. "There isn't any part of me that didn't think I'm a little bit vulnerable. I do talk shit," he says, as the very visible host of HBO's Emmy-winning Last Week Tonight. "Under another country's politics, that would be cause for deportation, or at least [the government] engaging in some form of fuckery. Like something out of Goodfellas: They open a door, plastic sheeting, Jared Kushner in a swivel chair stroking a hairless cat."

When he appeared at the federal building in lower Manhattan with his lawyer and his wife, Kate Norley (a former combat medic), for the naturalization ceremony, he was so nervous he blanked on his phone number. Eventually, Oliver, along with 159 other people from 49 countries, raised his right hand and took the oath. He was given a tiny American flag as Lee Greenwood's "Proud to Be an American" played and a photo of Donald Trump glowered from a wall. "The feeling you get at the end of that process is overwhelming relief," he says. "And that it's nothing to do with the current president."

"I would like this presidency to end because it's not good for America, for my personal health or for comedy in general. It's hard to find different ways to attack the same kind of despair," he says, a reminder that Oliver has chosen to become a card-carrying citizen at one of the most fractured, tumultuous times in modern American politics. In fact, Last Week Tonight will embark on its seventh season Feb. 16, just weeks after the Senate is expected to conclude its impeachment trial and smack in the middle of what already is shaping up to be a contentious Democratic primary. And Oliver, after a four-month hiatus, will be weighing in from an enviable platform: Last Week Tonight draws 5 million viewers each week, is consistently among the top series on HBO's digital platforms and routinely penetrates the helter-skelter news cycle (the 2016 segment "#MakeDonaldDrumpfAgain" racked up 85 million video views in its first month, a record for any piece of HBO content). A hard time to be an American but a fertile time to be an American satirist. Given the fact that his career clearly wasn't suffering as well as his disgust with the nation's current political leadership, why exactly did Oliver even want to become a citizen now? "Everyone in that room is making a commitment that long outlasts the current president," he says. "You're vehemently endorsing the idea of America because the idea is still perfect. That's what was so moving about the ceremony."

For Oliver, though, there's another component to it: Now when he scathingly sends up America's ruling class, it'll be with skin in the game. "If you're going to take swings, you'd better take ownership of the ground you're standing on. It's one thing being lectured to by a tourist; it's different being lectured to by someone who lives here. So that feels meaningfully different to me. It's your right to speak critically about the country that you have chosen."

***

A month after becoming a U.S. citizen, Oliver is in a bar in midtown Manhattan engaged in a decidedly less American pursuit: watching English soccer. The place is loud and dark and smells as if they've been mopping the floor with beer. "I've smelled worse," he offers with a grin. A lifelong follower of Liverpool, near where he was raised by schoolteacher parents before attending Cambridge, Oliver is on a text chain with fellow fans Mike Myers, Keegan-Michael Key and British comedian Daniel Kitson. Occasionally, he and Kitson record the matches so they can watch together, with Oliver in the U.S. and Kitson in London. "We press play at the same time; it's communal even when you're alone."

When Liverpool scores the only goal of the game against Tottenham, Oliver stifles a fist pump. Like fellow exiles Harry and Meghan, it seems, he has distanced himself from the U.K. while remaining loyal to his institution. "I completely understand why they're leaving," he says of the royals. "I don't think you need to have seen even an episode and a half of The Crown to realize this was not going to be the easiest family to marry into. I'm just amazed that people care as much as it seems they do." Oliver says his interest level is close to zero.

He is just coming off a two-week break for the winter holiday, during which he performed several stand-up shows in Portland, Oregon, and San Francisco. "I don't do it nearly as much as I'd like to just because I can't with a show that is all-consuming."

Last Week Tonight produces 30 episodes a year — in season two, HBO upped it to 35, then reversed course after Oliver felt it was burning out his 65-person crew — but the 12 staff writers work year-round. That includes Oliver, who often is the first one in and the last to leave the show's offices on West 57th Street, across from the CBS broadcast center, where the show tapes.

Tim Carvell (the show's executive producer, along with Oliver and Liz Stanton) is his closest collaborator; they shared an office at The Daily Show. But the rest of the senior staff also has been there since the show's inception. Stanton, who got her start in comedy on The Dana Carvey Show, pitched herself to HBO when she heard Oliver was coming over. But none of the senior writers had any TV experience when they started: Juli Weiner was a writer at Vanity Fair; Jill Twiss was a stand-up and did a stint in children's theater (she authored the show's Marlon Bundo book skewering Vice President Mike Pence); comedian Jeff Maurer was a speechwriter for the EPA; Dan Gurewitch came from The CollegeHumor Show.

The first season, the staff was crashing the desk pieces weekly. These days, they have settled into a more manageable schedule. "We have a better understanding of what stories we can pace production around and what is going to take us half a year," says Oliver. A 20-minute segment about televangelists and tax exemption, for example, was preceded by a seven-month correspondence between Oliver and Texas preacher Robert Tilton.

The staff begins putting together the show's shorter opening segment that recaps the week's news on Thursday so that it still will feel fresh by Sunday, when Last Week Tonight is taped before an audience at 7 p.m.

The show's deeply researched second segments — often on unsexy issues like bias in medicine (which featured cameos from Wanda Sykes and Larry David), standardized testing and mobile home leases — take about five weeks to produce (longer if they involve a Broadway song-and-dance number about a litigious coal baron that necessitates 50 dancers, a 21-piece orchestra and multiple all-night shoots in Times Square, like last season's penultimate episode).

Each piece typically begins with the show's six researchers (many with journalism backgrounds from outlets like The New York Times, ProPublica and BuzzFeed) who scour information about potential topics from media reports, academic studies and government documents. In the second week, the four footage producers gather the video they'll need to tell the story. A writer then creates an outline — a joke-free skeleton of the story with a coherent arc. The show retains outside lawyers to vet the script each week. There also is an HBO attorney assigned to the show who is involved throughout the whole process, including engaging with the target of the piece, which often "turns to extreme aggression," Oliver says with a laugh.

The show also will consult legal experts for specific segments. For instance, they hired a nonprofit attorney for the piece on televangelists and consulted with an employment lawyer for a segment about Vince McMahon's WWE. Only after the piece feels structurally sound do they begin making it funny. Finally, one or two days before air, the full writing staff gathers for punch-up. "You don't want them writing jokes on a beat that's about to get cut or on a fact that's about to get destroyed," Oliver says. "It can be really disheartening to see a fantastic joke on a statistic that turns out to be wrong."

Despite Oliver's command of political satire, Trump actually gets less attention on Last Week Tonight than he does on many other late night shows. "[Trump] takes up so much of the oxygen in the news," he says. "And when you're reacting to the news, that's all you're reacting to. We are in the very fortunate position where we can protect the vast majority of our show from him."

Oliver confesses that he does not like to talk about the show, and he won't preview what deep dives they'll be doing this season - mostly out of self-preservation. "If you describe any of the shows we did last year — SLAAP suits, the National Weather Service — you could go, 'Oof, that sounds like a miss-able one to me,' " he says. "Just hearing the subject in isolation would make you think, 'That sounds really bad.' "

The election inevitably will be a dominant theme this year — and beyond. "It would be insane not to assume that [Trump will get re-elected]," he sighs. Oliver has not worked out exactly how he'll interpret, or satirize, the 2020 campaign, though he allows that they will avoid "the daily grind of campaign nonsense" and instead focus on broader themes or policies. But it's clear he's consumed with the same existential angst that grips much of the country. "The whole point of this is to make a comedy show," he says. "But the deeper you go into a story, the more you realize how systemic certain problems are and the harder it is to believe that hope can exist. That bleakness is definitely corrosive."

And the news cycle does occasionally necessitate a total rewrite. In 2018, after Brett Kavanaugh's testimony in front of the Senate Judiciary Committee, which happened on a Thursday, Oliver scrapped the entire show for a 30-minute segment about the hearing, written in two days. He did the same last season after Trump's withdrawal of American troops from Syria. "It felt like it was worth giving people context around exactly why that was such a catastrophic decision," he says.

Sometimes a single joke — for the show's "Now This" interstitials, for example — can blossom into a full-blown desk piece, especially if it lends itself to an absurd prank. That's what happened when writers Weiner and Seena Vali began looking into Turkmenistan strongman Gurbanguly Berdimuhamedov and discovered his weird obsession with Akhal-Teke horses (he owns 600 and writes poetry about them) and Guinness World Records.

"Of course autocrats like Guinness," laughs Oliver. "All they crave is legitimacy on a global stage. And of course Guinness should not be empowering that."

When Oliver and his writers attempted to top one of Berdimuhamedov's records, they considered building their own giant horse-head statue (Berdimuhamedov has the largest) or topping Turkmenistan's record for "cycling awareness," but recruiting more than 3,246 participants proved unwieldy. So they baked the world's largest cake; it took Carlo's bakery in Hoboken, New Jersey (the same bakery in TLC's Cake Boss), three days (and 7,000 eggs) to create a 6,000-pound, 600-square-foot confection with an icing rendering of Berdimuhamedov taking a nasty spill from a horse. "We settled on the cake because it has a gross factor and it was just stupid," says Stanton. The bakers assembled the cake in the studio; they finished icing it 15 minutes before showtime.

***

Oliver did not set out to invent this new form of "aggressively researched comedy," as he puts it. Until he finalized his first deal with HBO in the fall of 2013, he was not contemplating a future outside of The Daily Show. Earlier that year, he had established himself as Jon Stewart's obvious successor after a summer fill-in stint while Stewart was directing the feature Rosewater. When Stewart returned that fall, the idea was floated to have Oliver host The Daily Show during the summers so that Stewart could take a regular break.

"He was fucking tired to the marrow of his bones," says Oliver. "It felt like the real asset is Jon, and if you can do anything to squeeze another couple of years out of this exhausted mule, then you should probably do it."

Comedy Central executives rejected the idea. Oliver's deal was up at the end of 2013. But by September, he had yet to finalize an extension, and HBO pounced. "Jon and I were telling each other everything [about the contract negotiations]. I think it would have been easier for Comedy Central if they were able to tell us two different things," says Oliver. "I didn't want to leave. I was so happy there. But that kind of forced me out the door."

He signed a two-year deal with HBO with an option for a third; he makes air quotes around the word "option": "There was no reason to believe, in my mind, that this show was going to work at all."

When Stewart announced in February 2015 that he would leave The Daily Show that August, Oliver was just starting his second season of Last Week Tonight. Internally, HBO executives worried Oliver would regret missing out on the opportunity to succeed Stewart, so his third-year option gave him the ability to change the format from a weekly to a daily program. "We quickly realized, 'Oh, hell no. This is hard enough in 30-minute form,' " he says. By that point, Oliver had achieved cultural cachet and awards recognition. Last Week Tonight has earned the Emmy for variety series every year since 2016.

Oliver's current deal, his second with the network, is up at the end of 2020. He won't reveal how much he makes, but an HBO insider characterizes the show as "inexpensive" — less than Real Time With Bill Maher, which has been on for 18 seasons and airs 35 weeks each year. Asked how long he sees himself doing it, Oliver shrugs: "I don't know what too long is. I just hope I'll know when it's approaching."

The host is in "sporadic" touch with Stewart, mostly about sports. Stewart also follows English soccer, and Oliver reads a recent email from him: "As a Mets fan, please explain how Liverpool are going to fuck this up."

Says Oliver, "It's only brief email check-ins with him." Stewart and fellow Daily Show alum Stephen Colbert remain on a professional pedestal. "Jon or Stephen will never feel like peers to me," he says.

When he needs to talk comedy and the rigors of producing a show, he leans on Late Night host Seth Meyers. "If I get a text from John about something that he liked, it's more often a really dumb joke that bombed with the audience," says Meyers. "And that is a true sign of someone who really has your back."

Oliver has appeared on Late Night several times, and Meyers had a cameo in the show's Lost in Translation-esque short film about Oliver's Japanese mascot alter-ego Chiijohn, Last Week Tonight's finale last season.

"John and his whole team appreciate how busy anyone who does a show like this is. So he was like, 'Hey, I'm going to send a couple of giant head-foam-wearing people over to your studio, it will take 10 minutes, and we'll make it as easy as possible.' You have total faith when you turn yourself over to them that you're in safe hands."

Non-comedians proceed with more caution. "I never thought of myself as being on his show," says Anita Hill, who was interviewed for a piece about sexual harassment. "It was a risk for me. But John does not take himself too seriously; he doesn't feel like he has to be the only person who has something to say. And the use of humor is effective." Monica Lewinsky says her reaction to being asked to appear was initially "flattery" then "panic": "But my brother pointed out that while John will stitch up many people, he never stitches up his guests." For the piece about public shaming, Oliver admitted to his own guilt when it came to making puerile jokes about Lewinsky. "I think that was brave," she says.

These conversations underscore Oliver's goal to move the conversation forward in a constructive way. They also highlight his capacity for empathy in contrast to the stereotype of the emotionally repressed Brit whom he claims to be. Becoming a parent, with all of its terrifying anxiety — and especially his wife's difficult first pregnancy, which resulted in the premature birth of their son Hudson, now 4 — brought up dormant emotions. They welcomed a second son in 2018. (The couple met at the 2008 Republican National Convention in St. Paul; she was there on behalf of the advocacy group Vets for Freedom, and Oliver was there for The Daily Show.)

"Kate was in the hospital, it was very difficult for months beforehand. And doing the show at the same time, it was the absolute worst," he stammers. "It was a surreal experience."

***

Oliver maintains that HBO gives him complete creative freedom. Even his frequent jabs at corporate overlords AT&T, which acquired HBO's parent in 2018 for $85 billion, have raised no alarms. Oliver has yet to meet AT&T CEO Randall Stephenson, but he did encounter WarnerMedia CEO John Stankey when he was in Los Angeles in September for the Emmy Awards.

"It was brief," Oliver says with a laugh. "We sized each other up and realized, 'I think we can get through this in 30 seconds.'"

Even a two-year court battle with coal executive Bob Murray, which cost HBO $200,000 in legal fees and resulted in a tripling of the show's libel insurance premiums, did not cause any "corporate hand-wringing," says HBO programming chief Casey Bloys. "The law was on our side, and the lawyers were confident. When you have someone like John doing something as special as he's doing, you want to do right by him. But watching him do what he does, you do realize the limitations you would have if you had corporate sponsors."

Without advertisers to rankle or, apparently, budget constraints, Oliver and his writers are free to pursue their most absurdist ambitions.

"John sees the humor in disconnects," says James Cromwell, who is among several Oscar nominees the show has enlisted for a series of short films starring Oliver's collection of wax presidents. “I’m sure it’s intended as a metaphor for the fact that we have a clown in orange face as president of the United Sates.” Oliver spent $13,700 to buy five of them from a now-defunct presidential wax museum in Gettysburg, Pennsylvania. In 2018, he also purchased $76,000 worth of Russell Crowe movie memorabilia (including $7,000 for the leather jock strap he wore in Cinderella Man). In response, Crowe tweeted a video featuring Australia's beloved Irwin family unveiling the "John Oliver Koala Chlamydia Ward." Crowe financed it with the auction proceeds from Oliver. “In no world do you really think he’s going to respond positively,” Oliver says. But Crowe's clapback, he says, "was comedically perfect — so structurally sound as a fuck-you because it raised awareness for a disease that is objectively funny, as appalling as it is for the koalas — and he actually did legitimate good. It's an almost shame-inducing perfect joke."

The following week, they wanted to open the show with a recorded message from Crowe. "He emailed from Australia, saying, 'Hey, I've recorded it, but I'm not sure this escalates the joke any,' " recalls Oliver. "And you kind of read it and go, 'Fuck, you're right. I can't believe I'm taking good joke notes from Russell Crowe. Thank you!' "

Trump, too, has played along — if unwittingly — insisting on Twitter and during multiple interviews that he repeatedly has turned down invitations to be on Oliver's show.

"It's a really discombobulating thing to think, 'I know you're wrong, but you are now more confident in your lie than I am in the truth.' So I said to our staff: ‘Please tell me — it’s fine, no one is in any trouble — if you just reached out to do any fact-check that could be construed as an invitation.' And obviously the answer was no. But it's dangerous how good he is at lying in a way that you feel like he could pass a lie detector test. And to lie about something so utterly worthless? Lying about being invited on our show is the lowest-stakes lie imaginable," says Oliver, the new American with still-decidedly British modesty. "You are just emptying your ego down the toilet."

This story first appeared in the Jan. 29 issue of The Hollywood Reporter magazine. Click here to subscribe.