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John Oliver Talks Trump Executive Orders and ‘Luxury’ of Long Segments on ‘Last Week Tonight’

John Oliver and the “Last Week Tonight” team could be forgiven for thinking that his HBO series has been a target of sorts for the Trump administration.

A number of the social, political and economic issues examined by Oliver’s weekly late-night series have been the subject of executive orders signed by President Trump as part of his rapid-fire policymaking process during the first two weeks of his administration.

“Over five days last week, each executive order related to a story we’ve done in the past three years,” Oliver said Monday during a roundtable with journalists to promote the fourth season of the show, which bows Sunday. He called it a “depressing exercise” for his producers to re-tweet links to stories on the fate of Iraqi military translators, the immigrant visa application process, and financial industry rules governing retirement and investment programs (“wave goodbye to it as it sails away in the distance”), among other topics.

Oliver said that despite the “all-consuming” nature of the 2016 presidential election, he tried to ensure that “Last Week Tonight” tackled more than the ascendancy of Trump last season, and he expects to do the same this year. Out of 30 episodes in 2016, just eight of the centerpiece stories were focused on Trump and presidential politics. “We were very anxious not make it all Trump, all the time, both on the level of interest and what the human soul can sustain,” he said.

The weekly format of “Last Week Tonight” has also forced producers to seek out issues that are rarely dealt with on other late-night comedy series. “As a benefit to us we’ve been pushed into covering things that no one in their right minds would cover for comedy,” he said. The flexibility of the show — which amounts to whatever producers think is best for the material — is a “luxury” that comes from working in the commercial-free atmosphere of HBO, he said. “We can be structurally ambitious with what we do,” Oliver said. (HBO chairman-CEO Richard Plepler sat next to Oliver in the conference room at HBO’s midtown headquarters, fairly beaming.)

Oliver pointed with pride to the 2016 episode that devoted almost the entire half-hour to exposing how multi-level marketing schemes take advantage of consumers. That segment was even redone in Spanish for online distribution because research indicated that Latin America is a big growth market for such companies. “Jane the Virgin” star Jaime Camil was enlisted to fill Oliver’s role of hosting the segment in Spanish.

Oliver was pressed about his view of comedy in the Trump era, and whether late-night hosts now fill a role of holding the powerful accountable.

“I don’t think it necessarily needs to change — you’ve probably got to work harder. That’s not necessarily a bad thing,” he said. “There’s lots of low-hanging fruit with administrations like this. You kind of need to reach past that.”

Among other observations during the hourlong Q&A session:

  • “Last Week” Tonight” wrapped its third season in November but the staff was back at work in early January. “I’m not cut out for relaxation on any level,” Oliver said.
  • Oliver strives for nuance in the show’s in-depth reporting, and it bugs him when viewer and media reaction to stories boils down to headlines declaring that Oliver “eviscerates” or “disembowels” the subject. “We work really hard to put a lot of nuance into a 20-minute story,” he said.
  • Oliver has a bipartisan fan base. “Conservatives come up to me and say ‘I disagree with you but I love the show.’ “
  • Research first, jokes later. Producers and researchers focus on nailing the factual elements of a story before they try to work jokes and humor into the storytelling — a lesson they learned through trial and error early on. “You can’t build a story on a foundation of sand,” he said.
  • Oliver is highly satisfied “when we do something irredeemably stupid,” and when he gets to see “a group of adults do a really silly, spectacular waste of HBO’s resources.” He pointed to the  creation of a miniature Supreme Court set that was populated with dogs, and an elaborate replica of the newsroom set from the Oscar winner “Spotlight” for a story about the state of journalism.
  • The native Brit said he’s still dismayed by the fact that his countrymen decided to leave the European Union in last year’s Brexit referendum, likening it to “watching a slow-moving car crash.” “It is impossible to overstate just how bad I think it is going to be for Britain (and) in Europe as a whole,” he said.

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