How President Trump Ruined Political Comedy

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Earlier this year, before everything happened, I went to New York City to survey the state of American political comedy, which has never felt more important — or more fraught. At a taping of “Full Frontal With Samantha Bee,” I met a woman from Astoria who had brought a birthday present for the host: a mock campaign poster promoting Ripley-Hicks 2020 — the two main characters from “Aliens” — emblazoned with the slogan “It’s the only way to be sure.” At “Last Week Tonight With John Oliver,” I watched the warm-up guy wring big laughs out of a malfunctioning T-shirt gun, firing three or at best four rows back into a house packed with cheering fans — people who seemed genuinely to feel part of a movement, a wave of laughter crashing against a president who was, if not washed away, bound to erode at any minute.

And then, on a blustery Thursday night, I went to the program that started it all: “The Daily Show.” From a soundstage near the western edge of Manhattan, I watched Trevor Noah put on a clinic in audience management. During one segment, he transitioned smoothly from his impression of the president to a righteous condemnation of sectarian violence in India, followed by a joke about green text bubbles. It was everything the genre now aims to be: breezily informative, morally upright and funny enough that the house knew when to laugh. After the taping, a Comedy Central representative led me backstage, down a hall that transitioned from production industrial to modern corporate décor, and through a warren of offices to a glassed-in conference room, where I met the head writer, Dan Amira, and the showrunner, Jen Flanz. Thinking about the difficulty of making political comedy that jibed with a broad audience, I asked if there was a type of joke they had learned not to do.

I was surprised when Flanz whispered “sarcasm,” but Amira readily agreed: “People are so emotionally invested … ” he said, trailing off for a second. “You almost have to not couch things in sarcasm, because people will momentarily wonder if you’re not on their side.”

Nodding, Flanz added, “We have to signal to the audience, ‘Hey, we know how you’re feeling,’ so it doesn’t seem like you’re making light of a serious thing.” Yet making light of serious things is the definition of political comedy. Here lies the problem facing “The Daily Show” and its offspring: Consumers of this brand of comedy are so horrified by Trump that irreverence can feel like betrayal.

From 1996 until the second term of the George W. Bush administration, “The Daily Show” was effectively the only program of its kind. In 2005, “The Colbert Report” gave the most popular “Daily Show” correspondent a half-hour of his own. The boom began almost a decade later, when HBO aired the first episode of “Last Week Tonight.” Since January 2015, another seven liberal clip shows have premiered: “Full Frontal,” “The Nightly Show With Larry Wilmore,” “The Opposition With Jordan Klepper,” “Patriot Act With Hasan Minhaj,” “Wyatt Cenac’s Problem Areas,” “The Jim Jefferies Show” and “The Break With Michelle Wolf.” As of today, all of those seven but “Full Frontal” have been canceled.

This boom and bust overlaps conspicuously with the political career of one Donald J. Trump. In theory, Trump should be the best thing that ever happened to liberal comedy. Five years ago, when he announced his candidacy after descending an escalator in a mall/apartment complex bearing his name, it briefly appeared as if he might be. Like so many others, this hope has not panned out. Maybe it’s the glut; in any form of humor, from sitcoms to barroom remarks, overproduction causes trouble. But there is also a sense, as the president talks openly about defying the results of the election, that satire has not accomplished what its champions believed it could. Even the professionals seem disillusioned. Before his show, Oliver took questions from the audience, and I asked him what comedy was like under this administration. “People say it writes itself — the worst kind of comedy,” he said. “As a human being and a comedian, I cannot wait for this to be over.”

The phenomenon of a president whose person is ridiculous even as he imposes reactionary policies is not unprecedented in the 21st century. “The Daily Show” thrived in a similar ecosystem under George W. Bush, who combined funny behavior (“misunderestimated,” mortal combat against pretzel) with an extremely unfunny policy agenda (“enhanced interrogation,” invasion of Iraq). The ability of “The Daily Show” to balance the political demands of its moment with the aesthetic demands of the half-hour comedy program — while simultaneously making millions of dollars — was a success that basic cable has struggled to replicate ever since.

Now that it has become the ur-text for a whole genre of television, it’s easy to forget that “The Daily Show” rose in tandem with another novel format: cable news. It was born the same year as MSNBC and the program’s perfect foil, Fox News. That channel’s psychotically friendly coverage of conservatives provided an inexhaustible supply of funny clips, which pushed “The Daily Show” toward a type of joke that Jon Stewart perfected: video evidence of some public figure’s ignorance or dishonesty, followed by the host giving voice to our outrage at what we just watched. This approach is familiar today, but at the time it was refreshing — particularly in the run-up to the invasion of Iraq, when media outlets across the political spectrum seemed to uncritically echo Republican talking points.

Now this format faces an identity crisis, for two reasons. First, the media does not play along with President Trump; it is openly contemptuous of him, in a way that shunts comedians out of saying what we’re all thinking and into the more difficult position of topping what we’re all saying. Second, Trump’s success has proved that pointing out hypocrisy doesn’t work — not, at least, as a way to thwart the hypocrite. As a way to attract the 18-to-34 demographic, it remains a reliable tactic.

“The Daily Show” lost about a third of its viewers when Stewart left in 2015. In the intervening five years, it has recaptured that audience and then some, thanks to the charisma of its new host. Perhaps because of Noah’s likability, the post-2015 “Daily Show” has steered away from acerbic jokes and toward observational humor coupled with declarations of broader progressive values. It reserves almost all its venom for the president, partly because Noah does a fun Trump voice — a pastiche of Jerry Lewis and Master Shake whose humor is inversely proportional to its accuracy — and partly because that is one point on which its audience reliably agrees.

This shift in tone has changed the mythology of the liberal clip show. Stewart began as an upstart — the former MTV personality who was on so late, on such a high-numbered channel, that he could say what others would not — and he preserved that image even after he became a giant in political entertainment. The Trump-era liberal comedy show, on the other hand, casts its host not as a sharp-tongued outsider but as the leader of a righteous movement.

Everyone involved seems to accept that this movement is only a conceit. As Amira told me, “If you’re putting your faith in satire to take the president down, I think you’re hoping for too much.” Even as liberal comedy has become more explicitly political, it has rejected the possibility that comedy can move politics. That conclusion would seem reasonable were the right wing not presenting strong evidence to the contrary.

The challenges facing liberal late-night entertainers are exemplified by Colbert, who is arguably the biggest political-comedy success of the last two decades. As host of “The Colbert Report,” he developed an archconservative character whose willingness to bend any issue to Republican orthodoxy became a kind of high-wire act. Colbert’s commitment to this bit was almost total. Because he consistently spoke as Stephen the right-wing maniac and almost never as Colbert the liberal entertainer, audiences could stop worrying about whether he meant what he was saying and turn their attention to scanning it for ironic double meanings. The pleasure of his act came from watching him manage both levels simultaneously: He was skilled enough to improvise in character even as he constructed a second, liberal commentary on his conservative bromides. His humor emerged from the tension between these messages, placing his work within an ironic tradition that includes Mark Twain and Jonathan Swift. As the host of “The Late Show” — a job that calls on him to not just make jokes but also interview Margot Robbie and wranglers of exotic animals — Colbert has been deprived of his sharpest tool. Irony in politics, meanwhile, has reversed its polarity.

In their early days, Colbert and Stewart played off conservative foils who had aligned themselves firmly with sincerity. The Bush administration piously courted the religious right, and Fox News embraced a post-9/11 patriotism that seemed to deny the very existence of irony. But in the Trump era, liberals have drifted away from irony even as the right has embraced it — not just as a rhetorical tool but also as a means to advance joke versions of its actual agenda, in ways that make it hard to distinguish between the two.

This ambiguous irony deliberately refrains from signaling itself, forcing audiences to fall back on what they know of the performer to decide what’s being said ironically and what is sincere. This is the approach that propelled and then detonated the career of Milo Yiannopoulos. The former Breitbart editor was known for stunts like jokingly setting up a scholarship fund for white men, before leaked emails revealed that he had also solicited story ideas from white supremacists. His audience finally collapsed after he appeared to defend pedophilia, a position he later claimed to have taken sarcastically.

Trump’s success has proved that pointing out hypocrisy doesn’t work — not, at least, as a way to thwart the hypocrite.

Comedian-pundit figures have proliferated on the right in recent years. There’s Steven Crowder, whose popular YouTube channel was demonetized for over a year after he made a series of jokes about the race and sexual orientation of the Vox journalist Carlos Maza. There’s also Fox News personality Jesse Watters, who once billed himself as a humorist but now co-hosts the straight opinion program “The Five.” Like Yiannopoulos, Crowder and Watters have deflected criticism by saying they’re just doing comedy — often expressing astonishment that anyone would take them seriously at all. The conservative brand of ambiguous irony looks to create asymmetries in how insiders and outsiders interpret what is being said, so that any statement that gets too much blowback can become someone else’s failure to take a joke.

This approach lets irony serve as a stalking horse for ideas that decency prevents the ironist from advancing seriously. All three men construct jokes that operate in a gray area between tweaking political correctness and simply repeating the prejudices it forbids. After Nike closed American retail outlets in response to the coronavirus but left open stores in China, Crowder called customer service to complain that the decision was racist — using what you might call a funny Chinese voice, if you were to loosely interpret the words “funny” and “Chinese.” In a segment on “The Five,” Watters proposed bulldozing a swath of downtown Los Angeles and institutionalizing the homeless who lived there. Crowder’s and Watters’s audiences read such jokes as satire, and they delight in the reactions of “triggered” liberals who take them seriously. Ambiguous irony lets the ironist and his audience laugh twice: first at the joke, then at whoever doesn’t get it.

As liberal infotainment has turned away from sarcasm in favor of straightforward indignation at a news cycle that often feels absurd already, conservatives have taken up ambiguous irony as a way to provoke critics and thrill audiences. They are succeeding. Crowder’s YouTube channel has 4.8 million subscribers, and Fox News has given Watters his own hourlong show. These hybrid entertainer-pundits have risen to the top of a cable-internet ecosystem that contains dozens of less successful competitors, as well as legacy provocateurs like Michelle Malkin and Ann Coulter.

Today’s right is at once more willing to say what it doesn’t mean for a laugh and more ready to frame what it does mean as a joke. At a moment when American conservatism is flirting with ideas that have been outside the realm of mainstream politics for 50 years, ambiguous irony has allowed both political comedians and pundits to say what cannot be said. In order to avoid having their jokes mistaken for dog whistles, the “Daily Show” staff has learned to let the crowd know when it is kidding. Right-wing comedians have made an entire style out of doing the opposite.

The conservative humorist who has found the most success with this technique is now the President of the United States.

Even if you don’t find Trump funny at all, you must admit that you are resisting a lot of attempts. In terms of volume, Trump may be the jokiest president in American history. His impression of Michael Bloomberg, in which he crouches behind the lectern so that only his head is visible, is a genuinely funny sight gag — partly because of its economy and partly because of its audacity. What other president would stoop to it? Even Ronald Reagan, who once starred opposite a chimp, would never resort to pantomime. In his love of insults, his penchant for hyperbole and his commitment to shtick — that knowing performance of himself that blurs the line between personality and persona — Trump is unprecedented among American presidents.

The most striking feature of his rhetorical style is how much it resembles that of a nightclub comic. He is known to work out material on the road, presenting rally audiences with variations on the same bits until he develops something that works. The idea of a border wall with Mexico is rumored to have emerged from this process. His unhurried delivery — which eschews setup/punch rhythms in favor of a meandering conversation with the audience, punctuated by audacious remarks — calls to mind a late-career Don Rickles. Unlike Rickles, though, Trump rarely laughs. He delivers his jokes in the same tone he delivers serious remarks. The insult comedian always ends by telling his victim he’s a good sport, but Trump doesn’t offer such signals.

In October 2019, for example, he tweeted a photograph of himself giving the Medal of Honor to a dog. This event did not happen. The conservative website The Daily Wire created the image by photoshopping Conan, the U.S. Army dog that helped kill Abu Bakr al-Baghdadi, into an existing picture of Trump awarding the medal to the Vietnam combat medic James C. McCloughan. On the Louder With Crowder website, the writer John Brodigan ridiculed The Times and the CNN White House correspondent Jim Acosta for reporting that the image was doctored, writing, “You’d have to be an idiot to think this actually happened in real life.” But the president gave no indication that the photo was a joke; he simply tweeted “AMERICAN HERO!” and the picture. A close acquaintance of mine, who is not an idiot, saw the photo on Facebook and assumed Trump had in fact given the medal to a dog. She thought it was absurd, but she did not assume it was ironic, because what previous American president has disseminated fake pictures of himself performing official functions?

Such applications of ambiguous irony allow President Trump to embarrass conventional media in ways that exhilarate his supporters. Organizations like The Times and CNN have to take the president seriously. When he says something that isn’t true, they must soberly point out that it isn’t, even when the intent of the untruth is not to deceive but to achieve some rhetorical effect. As a result, news organizations unequipped to cover an ironic president get lumped in with partisans who misconstrue his irony in bad faith. Both groups are cast as humorless scolds, solidifying the loyalty of MAGA types who think of themselves as in on a joke the media does not understand.

Ambiguous irony also lets the president hedge his bets. Trump is constantly saying things he doesn’t mean (Jim Acosta is “a real beauty”), or things he kind of means but goes on to retract (his authority is “total”), or things he didn’t mean at first but later does (“build the wall”), or things nobody thought he meant that he apparently did (“lock her up”), as well as things he seemingly did mean before he retroactively declared them sarcasm — like his televised claim that injecting bleach might stop the coronavirus. Ambiguous irony opens up space for Trump to revise the meaning of his statements later, when he knows how they have played.

This miasma of ill-defined but ever-present irony makes Trump virtually impossible to mock, because that job is taken. The real Donald Trump acts as if he’s doing an impression of some normal-looking, occasionally self-aggrandizing president we don’t know about. His supporters know this impression is fake. They don’t think Trump is the guy he pretends to be; they know he is the guy who pretends to be that guy, which is a hilarious thing for the president to do. Trump has effectively neutralized political comedy by shifting the place where jokes happen from the soundstage to the White House. The unsettling thing about this approach is that it works — not just as a way to defang satirists but also as a way to wield power.

Trump doesn’t seem willing to abandon the bit, no matter how dire things get. At the beginning of April, in response to a question about statistical models forecasting coronavirus mortality rates, he said: “The professionals did the models. I was never involved in a model — at least this kind of model.” Mr. President, you dog. Without missing a beat, he went on: “But you know what? Hundreds of thousands of people, they say, are going to die.”

This moment seemed to augur the final triumph of politics over comedy. “The Daily Show” and its imitators had been exiled from their studios by the crisis, but Trump still got to do a few minutes every night — at least until the virus found its way to him too. It’s an astonishing outcome that, like the best punch lines, seems inevitable in retrospect. Only it’s not funny, because the joke is on all of us.

Dan Brooks writes essays, fiction and commentary from Montana and abroad. He last wrote an article for the magazine about folksy political advertisements.