Saturday, March 8, 2025

Tonight I Want to Talk About John Oliver, Part 2: How He Kept His Job As All Around Him Daily Show Alum Were Losing Theirs - And How His True Beliefs Only Emerged During Biden's Administration

 

 

Of all the decisions the Democratic Party made in the aftermath of the 2016 election, one of the most illogical was their apparent decision to increasingly use Hollywood as part of ‘the resistance’.

This was a foolish decision more multiple reasons on the parts of the Democrats. During the 21st century the right had managed to brand them as out-of-touch liberals run by the coastal elites a weapon that had constantly cost Democrats elections they should have won. To more or less double down on this was not going to help them win back the white working class voter that was increasingly going Republican. More to the point Hollywood, including the new breed of late night hosts, had almost non-stop been anti-Trump for more than a year – and Trump had won.

For Hollywood as well as late night, the results of the elections should have given them cause to look in the mirror about how realistically they could change the minds of the electorate considering how spectacularly they had failed. They had already isolated nearly half of America during 2016 and it had not resulted in Hilary Clinton becoming President. And considering that by 2016 the economic shakiness across the industry was starting to be felt in network television and cable, the idea of continuing to go harshly against the Republicans and Trump in the aftermath could only hurt their ratings and the economic health of the industry.

And yet Hollywood decided not to regroup but almost entirely to double down on the anti-Trump rhetoric in the aftermath of the election. The reasons would seem to be based in the combination of Trump derangement syndrome and the left’s unwillingness to accept a reality that doesn’t fit their world view. There was no attempt from any part of the industry, certainly not late night, to try and understand the electorate. After all, they were all set in LA and New York and the elitist strain has always been strongest there. And to many it confirmed deeply held beliefs, far more prominent among the left then the right, of the inferiority of the American people intellectually. The electorate was brainwashing by Fox News, they hadn’t gone to the right schools, they lived in flyover country. They weren’t real Americans.

During the era of Trump many new late night shows debuted on cable and streaming led by former Daily Show alum: Larry Wilmore, Wyatt Cenac, Samantha Bee and Jordan Klepper would all host shows during this period. Very few lasted very long. Their defenders will argue it because of the racist and sexist nature of American institutions, late night being one of them. They will also argue that the election of Donald Trump killed off much of the demand for either liberal humor or made satire impossible.

But having watched quite a bit of all these shows I’d argue there’s a far more viable counterargument. Though all of them had worked for Jon Stewart for an extended period, all of them seemed to have forgotten why his tenure of The Daily Show had been both a critical and ratings success: he never took sides. He attacked the Democrats as often as he did the Republicans, he went after the failures of both MSNBC and Fox News, and while he no doubt had many reasons to be angry during that period, he rarely let it show in his broadcasts. He always went out of his way to use a light touch and he knew his first job was to be a comedian.

The same can’t be said of Problem Areas , Full Frontal or Jordan Klepper’s attempt to satirize Alex Jones. None of these hosts were interested in trying to win over the masses, being funny, or even being entertaining. What they were interesting in was essentially using their shows to express grievances and vent their rage in the guise of entertainment. It’s not like there wasn’t merit to exploring the failures of policing in America as Wyatt Cenac did or for Samantha Bee to argue about the misogynistic behavior of so many Republicans. But none of them were making a real effort to try and be entertaining – or more importantly, try to make their programs acceptable to people who weren’t already open to their way of thinking in the first place. Their shows were there to preach to the converted and as has been historical true, that’s always a smaller audience than the left wants to admit. Cable was brave to give them these chances but they went out of their way to avoid being accepted by the masses. Hollywood is a business and they failed at it.

John Oliver managed to keep Last Week Tonight going during this period, paradoxically, because his was perhaps the only late night comedy show where Trump wasn’t ever present during his first term. He dealt with him in the openings of every episode, and when it came to certain aspects of domestic and foreign policy he was prominent but by and large Trump was only a bit player between 2017 and even up to the final months of 2020.

Oliver spent much of this time dealing with foreign policy and corporations then the administration. He talked about the fallout from Brexit, the possibility of a right wing take over in France, the lead up to an Modhi’s second election in India. He talked about the elections across South America and Mexico. He talked about the opioid crisis and the evil of Richard Sackler. He talked about the coal mining industry and he talked about lawsuits. Part of the reason Last Week Tonight was perhaps the only late night show I watched consistently during that period was because unlike every other late night show, I never knew what I was going to see.

To be sure Oliver did bring up some of the leftist things involving social injustice during this same period. He talked about mass incarceration, police shootings, and the failures of the criminal justice. He talked about critical race theory, what it was and what it wasn’t. He talked about abortion and birth control. He talked about the filibuster and the electoral college. But because most of them were subjects late night and even reporting dealing with and because he made it entertaining, it was very hard to say that he was floating a liberal agenda.

During the year of COVID he spent much of 2020 and 2021 in a void, which eventually developed a personality and talked to him. Nevertheless he basically remained aloof from the election for much of 2020. To be sure he did lean into discussion of the electoral college even harder then, warned of Trump’s second term, and said election night might not be fun. (Understatement.) But even then it was hard to argue he was more left-wing then his colleagues.

The problem with John Oliver began when Biden was elected. And it should be noted it was a different kind of crisis then other late night hosts faced. In hindsight November of 2020 may be viewed as the last chance late night comedy had to save itself. By that point, audiences across the board on network had shrunk dramatically and the pandemic had shut down Hollywood and further damaged revenues. Furthermore it was the pattern of all late night, once a new President was back in office, to devote all of your energy to mock that President and whatever party was in power. The smart thing would have been to do just that.

Not a single late night show chose to follow that path. They had treated the Democrats fairly lightly during Trump’s term, during Biden’s administration they allowed him to escape untouched. The Republicans were always going to be the villains no matter how incompetent or how plagued by internecine warfare they were, no matter how inadequate they were at passing legislation. The Republicans were the enemies, little more than human. And if that met half the country chose not to watch any of their shows, if that meant their industry suffered as a result, so be it. Late Night had embraced part of the leftist doctrine where morality is the only goal. All Republicans were evil and they didn’t even deserve to be entertained.

Last Week Tonight took a different path – and it was here that Oliver real politics came into play. Oliver had always been uneasy with the alliance with the Democrats unlike the rest of late night  but his mindset was no doubt closer to the Democrats with the left. They needed to get rid of the greater evil and that meant disposing of Trump. The problem was that the left’s allegiance to Joe Biden more or less ended the day he became President and they started sounded the argument there was no difference between the two parties. This would be seen in many academic journals – and prominently on Last Week Tonight.

In the midst of 2021, America completed its pull out of Afghanistan where they had been inured for a20 year quagmire. By this point public support for our presence there was non-existent, and people had been wondering for multiple administrations why we couldn’t just leave.

Oliver seemed to be the only prominent voice arguing that America’s decision to withdraw was a mistake for humanitarian reasons. He excoriated Biden for not having any empathy for the Afghani people and gave no mention to the tens of thousands of American lives who had been lost in this war. It was the first time in my memory that I realized how far outside the mainstream Oliver’s beliefs could be. It was far from the last.

During the next year and a half after John Oliver returned to his studio, he continued to excoriate every part of the institutional world. And it was here that his unpleasantness, prominent in leftists, became obvious. When Queen Elizabeth died, he showed footage of Irish footballers chanting ‘Lizzy’s in a box’ exuberantly and was clearly chuckling when he came back. This followed a series of lectures on both Charles and the monarchy, much of which was valid but much of which followed the leftist dogma towards colonialism over all. There had been signs over the years that Oliver had the leftist version of blaming the West for not having the far left values of today, it became infinitely more obvious when Trump was gone.

Increasingly he began to argue about the failings of America, including student loans, the failings of the health care system and the government safety net. He’d done programs like this during Trump’s term but now that Biden was in office he seemed more determined to argue that correcting these evils was something that Biden had a moral obligation to do. He had, it must be remembered, previously done many shows about both the filibuster and the evil of the executive branch when Trump was in office as an abuse of power. Now he seemed to be arguing for Biden to use those same powers for the progressive agenda – and seemed to ignore the obvious contradiction.

Perhaps the strangest show Oliver ever devoted Last Week Tonight to was Law & Order. In previous years he’d actually used regulars from Law & Order in many of his comedy sketches to point out the flaws in policing. Now he spent an entire episode excoriating many of the cast members and the series that they worked on for presenting a false picture of what the criminal justice system was like. He also argued that whatever good things the cast members had done as a result of Law & Order were tainted by the fact that they working for a show that painted this false picture. Oliver went out of his way multiple times to argue that Law & Order was a drama and not supposed to be a documentary

I’ve spent the last two years wondering why, with all the problems the world was facing in 2022, why did Oliver devote an entire show to a fictional program, and couldn’t even explain why he was attacking it with the same harshness he did the actual criminal justice system? Only recently have I come up with some theories, all of which point to Oliver’s politics.

The first: purity Hollywood is known for being the most leftist organization in the country and in the Trump administration, almost every aspect of entertainment would lean into the credentials. There has always been a group that argues that no institution can ever be purely leftist – the word ‘neoliberal’ was coined for this purpose. Oliver wanted to make clear to his audience that he was had the pure leftist credentials even though he was part of Hollywood.

The second: pedantry. Law & Order has throughout its run made plotlines that have to deal with many of the progressive ideals that Oliver has spent his career advocating for and that powerful white men are responsible for it. And because it’s a procedural it can end its show arguing that justice can prevail against the rich and powerful, even if the audience knows in its heart the system doesn’t work that way. Oliver, who wants to be a truth teller, hates even the illusion that these things can work out even in fiction. Like many leftists, he likes his audience in sackcloth in ashes – which is not the best look for an entertainer.

The third: jealousy. Law and Order has always been watched by millions of people and is a cultural phenomena to this day. It will no doubt last forever. John Oliver knows that a comedian’s life has an expiration date and that is true of all entertainers. This may be a perverse form of wish fulfillment.

And I think now, it’s worth asking a valid question. What makes Last Week Tonight different from the shows of Sean Hannity or Rachel Maddow? There are no interviews, just a lot of stock footage which is framed to form a narrative that Oliver wants his viewers to see. He himself has joked about how depressing his show can be and how much of is a lecture. Because he’s an entertainer, he doesn’t have to bother with alternate points of view or the illusion of fairness. There are times he will say things with legal consequences “Now I have to tell you” he says every time someone gives a counterpoint, but he makes it very clear to his audience that he thinks that his targets are lying and that he is the truthteller. He knows his audience as well as anyone on cable news – and just as conservative media, he is a white man.

There have been constant arguments on the left as to why there is a progressive equivalent of Fox News out there to ‘counteract the brainwashing of the right’. I would argue Oliver has been, certainly for the last five years, as close to that equivalent. He certainly has all the trademarks of the progressive as I know him: academic, strident in his lectures, arguing for a progressive world view, hating conservatives with a passion – and most critically, not thinking the Democrats party is a solution but rather part of the problem. There’s a contingency in British politics referred to as ‘The Loony Left’ and Oliver pretty much checks all the boxes for it.

So what’s the difference? Last Week Tonight doesn’t have anywhere near the audience of either Fox News or Newsmax. It’s audience is like most of late night, mostly the educated, primarily college age people – in other words, they are already inclined to agree with what Oliver is telling them. This is hardly MAGA country and its unlikely to involve swing voters.

This would be fine if John Oliver were satisfied in his role as an entertainer. But in the leadup to the 2024 election it became very clear that he, like so many people in late night, began to think his audience was America and that he had the power, like so many on the new left want, to change the electorate.

In the next article in this series I will deal with Last Week Tonight in the leadup to the 2024 election and how it showed that like almost everyone else in Hollywood and the left, John Oliver hadn’t learned a thing about the electorate during that period.

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