Howard Anglin: Jon Stewart is back in the big chair. But what about his courage?

I don’t remember who said that the story The Emperor’s New Clothes has the wrong ending, but I’ve never forgotten it. In the canonical version, the story ends when a guileless boy speaks up and punctures the craven complicity of the crowd, none of whom had been willing to say what their eyes could plainly see. However, if the story were accurate it would end with the crowd turning on the boy and tearing him limb from limb for exposing their cowardice. The moral of the story is that truth-tellers can expect to be treated as enemies of society. 

This came to mind when I heard that Jon Stewart will be returning to the Daily Show desk for the presidential election season. Comedy Central is betting that Stewart plus Trump will equal ratings, but his old fans have loftier ambitions for him. They hope that Stewart will provide the kind of opposition to Donald Trump that neither Kamala Harris nor Joe Biden can. But will the 60-year-old comedian play along? Or will his conscience get the better of him?

When Stewart took over the Daily Show in 1999, it wasn’t a political show. Stewart made it that. He also made it a ratings hit and a cultural phenomenon, and he did it (at least initially) by making politics a source of comedy, rather than the other way around. Yes, he leaned Left, but that’s Hollywood, and yes he targeted Fox News, but back then Fox’s talk news format was new and newsworthy. It’s easy to forget, but in Stewart’s early years, CNN and MSNBC had not yet become bizarro-world Fox News. Glenn Beck was still a CNN host, and Rachel Maddow was just an occasional guest on Tucker Carlson’s show…on MSNBC.

Now, the media landscape is all Punch-and-Judy and the closest thing to Stewart’s old show is John Oliver’s Last Week Tonight, which runs the comedic gamut from smug to sanctimonious. Actually, that’s not fair—sometimes it’s also sneering. Stewart can’t be blamed for the decline of the news, but he bears some responsibility for the state of political comedy. By the end of his run, his act had congealed into schtick, and though he had the sense to leave the stage, his success taught a generation of imitators that if you pull a silly face, no one will notice that you have nothing to say.

Stewart’s return starts with one big advantage over his whilom proteges: he can be funny. Another advantage is that he actually seems to care about normal Americans. His charity work, for example, is mostly in support of veterans and first responders. Finally—and most promising for anyone hoping for something more than a weekly court jester for the DNC—Stewart has a cranky independent streak that means he can sometimes surprise, as he did in an infamous appearance on Stephen Colbert’s show at the end of the pandemic.

The segment is worth watching if only to pinpoint the exact moment when Colbert’s expression shifts from discomfort to panic. It’s right about the time that Stewart asks, with mock bewilderment: “Novel respiratory coronavirus overtaking Wuhan, China. What do we do?” and answers, “Oh, you know who we could ask? The Wuhan Novel Respiratory Coronavirus Lab. The disease is the same name as the lab. That’s just a little too weird, don’t you think?” By then, Colbert looks like a Soviet factory worker who’s been caught laughing at Stalin’s moustache. 

The clip went viral because it was funny, but also because it was shocking to hear a member of the ruling class say what everyone else could see. Occam call your office! Predictably, all the right people were offended. Newsweek ran a whole article of reactions from Stewart fans who felt betrayed by his defection from the approved narrative. It concluded with the solemn note that Newsweek “has contacted…the Embassy of China in Washington, D.C. for comment.” Because the Chinese Communist Party are experts in political humour, I guess. 

So, what can we expect from the revamped Daily Show? I’m sure Stewart will delight his critics by skewering Trump like a cheap voodoo doll, but Trump’s follies have been headlines for eight years. How many laughs are left to be squeezed from that well-juiced orange? The more interesting question is what will he say about Biden? Or, bluntly, will he say anything at all? Can Stewart really avoid criticising the man who is, after all, actually the president of the United States (and don’t comedians pride themselves on speaking truth to power)? 

Even before Biden entered his “What are we going to do about Grandpa” phase, he was among the ripest targets for ridicule in Washington, which is saying a lot. As VP, he was the inspiration for The Onion’s funniest running gag during the Obama years. There is simply no way a political comedian can’t see the comedic potential in the 81-year-old president, or in his actuarially-likely heir-apparent, Kamala Harris. The question is whether Stewart is honest enough to exploit it. 

America in 2024 is a satirist’s dream. It’s imperial Rome begging for a Juvenal. And if you think that’s all the fault of Trump and the Republicans, then you’ve been watching too much John Oliver. Federally, the Democratic party has all but given up on improving education, crime, budgeting, borders, and defence. And the major cities, which are run as experiments in applied progressivism by Democratic Party machines, have descended so far into squalor that if the Four Horsemen of the Apocalypse rode into town, they’d find nothing left to do. 

That is not to let the venal GOP leadership off the hook; rather, it’s to make a point that Stewart himself has made repeatedly in recent years, which is that America’s problems run deeper than Trump and Biden. On a self-described “anti-establishment” podcast, Stewart called the “two-team paradigm’ of “Right and Left” in American politics a “false dichotomy [that] clouds the conversation” about the corruption of incentives in politics and the media. And on his recently-cancelled Apple TV show, he tore into the media for covering politics like professional wrestling in their breathless overhyping of the “Russiagate” story.

If that is really what Stewart thinks, maybe there’s a chance he can avoid getting sucked into performing comic colour-commentary for the presidential horse race and, instead, use his platform to expose the whole enterprise as hopelessly rotten. Of course, if he does that, no one will be more surprised—and outraged—than the fans who tuned in to see him pummel Trump while pulling his punches on Biden. And if he does decide to be honest and say what anyone with eyes can see—about Trump, Biden, Harris, the party system, the media, all of it—he should be prepared to be torn apart by his own crowd.