Rob Dobi

There can be comedy in futility. John Wilson knows this, maybe better than anyone. While walking around midtown Manhattan with his camera before the pandemic, the documentarian spotted the actor Kyle MacLachlan on the opposite side of the street and gave chase. 

“I was filming him for a good five, 10 minutes until he goes down into the subway,” Wilson says. “And he didn’t notice me, the entire time. I’ve become pretty good at keeping a distance and hiding myself.” 

Once inside the station, the silver-haired, bespectacled Twin Peaks star reached a turnstile and began swiping his MetroCard. And then he kept swiping it. And swiping it some more. The damn thing wouldn’t work. Finally he stopped, and presumably went off to find a new card. 

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MacLachlan’s experience is relatable, and not just to those who have used the MTA. Uncontrollable forces occasionally interrupt everyone’s daily routine. Stars—they face minor inconveniences just like us. The moment, a highlight of the first episode of the HBO docuseries How to With John Wilson, is extraordinary in its mundanity. MacLachlan isn’t even identified; if you don’t watch closely you might miss him. “I love putting material like that in my films, without really acknowledging it, or giving any real context,” says Wilson, who collaborated with co-executive producer Nathan Fielder on the show. “Because, I think, it turns into one of those moments where you do a double take.” 

In Wilson’s New York, there is no B-roll. Every piece of footage, from a rat poking its head out from a pile of garbage bags to a small child in a stroller eating a booger, is a specific slice of city life. How to ..., which Wilson narrates in his pleasantly stilted voice, is full of these oddly affecting images. Whether it’s with an A-lister flummoxed by public transportation, a lonely young dude searching for meaning on spring break, or an anti-circumcision advocate happily stripping naked to demonstrate his foreskin restoration device, the filmmaker uses empathy to reveal his subjects’ vulnerability. The show isn’t a comedy in the traditional sense, but its frequent laughs serve to cut through the tension and anxiety of living in the eroding world that it depicts.

To Adam McKay, there’s something refreshingly defiant about Wilson’s portrayal of an America not usually seen on television, one where (most) folks are trying to make the best of what’s become a precarious existence. “He and Nathan Fielder get to the lonely post-community sadness behind all the success propaganda we’ve been hammered with for 40 years,” the blockbuster comedy director says in an email. “They show the sweetness of the people struggling to make reality match the Range Rover commercial we keep expecting our lives to be.” 

Since 2016, those paid to make people laugh have largely struggled to spin decades’ worth of disillusionment into comedy. The outgoing president is beyond parody, and his term, what with unprecedented income inequality, rising white supremacist violence, inhumane immigration policy, catastrophic climate events, and a virus that’s killed hundreds of thousands of Americans, is far too ugly to be funny. Yet as satisfying as it will be to see President Donald Trump go this month, the problems that he both caused and exacerbated are not exiting with him—meaning that many of the obstacles facing comedians will remain, as well. So in a way, the next era of comedy will likely resemble the most successful instances of the past era, the ones that captured the feel of the country with humor by removing the villain from the picture. 

“I mean, the reason we’re in this situation,” says Wilson, whose show had a strict no-Trump policy, “is because someone decided to give him airtime to begin with.”

For much of the first decade of the 21st century, Adam McKay spent his time examining the sort of man-children who’d come to dominate the American consciousness. First there was Ron Burgundy in Anchorman, then Ricky Bobby in Talladega Nights, and finally Dale Doback and Brennan Huff in Step Brothers. But then McKay zoomed out, and started to focus on the country that enabled and propped up such fools, ones who were often much more malevolent in real life. In 2010, he made The Other Guys, a screed against corporate greed and malfeasance disguised as a buddy cop movie. His advocacy grew only more overt from there: in 2015, The Big Short, an adaptation of Michael Lewis’s book about the housing bubble and financial crisis, and in 2018, Vice, an intentionally farcical biopic of Iraq War mastermind Dick Cheney. On the TV side, he signed on as an executive producer for Succession, a deeply cynical, deeply hilarious series that takes aim at the über-rich, morally bankrupt assholes who control American media. 

[John Wilson] and Nathan Fielder get to the lonely post-community sadness behind all the success propaganda we’ve been hammered with for 40 years.
Adam McKay

“The world is in such a state of massive, cartoonish, and frightening change that I think comedy is confused right now,” McKay said to me in 2019. “Donald Trump, Boris Johnson, Alex Jones, oil CEOs pressing forward with destroying our livable atmosphere, absurd false news stories about pizza parlors with sex rings in the basement and then real stories about billionaire pedophiles. … What the holy hell?” 

Over the past four years, TV has proved more capable of capturing this feeling. Barry, starring Bill Hader as a Marine turned hitman turned actor, wrestles with both the psychological trauma of war and the pitfalls of trying to make it in Hollywood. The Boys, about a team of lab-grown superheroes who are the literal byproduct of the military industrial complex, imagines what it would be like if all-powerful beings existed in the modern world. And The Righteous Gemstones, which centers on a family of televangelists, skewers greed-as-religion. “Serving the lord,” the show’s tagline reads. “And themselves.” Now, amid a scourge of several kinds of denialism, McKay is shooting what can be best described as a satirical tentpole called Don’t Look Up. The Netflix movie follows astronomers, played by Leonardo DiCaprio and Jennifer Lawrence, who go on a media tour in an attempt to convince disbelievers that there really is an asteroid heading for Earth. 

There’s a reason this kind of bleak, absurdist comedy has felt so of the time, despite not explicitly acknowledging the president. While he has undoubtedly necessitated sharper satire, the need for incisive comedy predates him. Trump’s America existed well before he took office. And it will exist long after he’s gone. Exploring how and why that’s the case is much more interesting—and important—than exploring Trump himself.

Which brings us, of course, to Sacha Baron Cohen. When he grew out his mustache again for Borat Subsequent Moviefilm, the most memorable cinematic comedy of a deeply miserable 2020, he made sure to position “McDonald Trump” as the main antagonist. But then the Kazakh journalist and his daughter (played by the hilarious Maria Bakalova) spent 96 minutes interacting with a wild cast of characters that range from a shady plastic surgeon to Conservative Political Action Conference attendees to conspiracy theorists to a ghoulish Rudy Giuliani. 

To Cohen, the stakes of the Borat sequel were higher than the 2006 original’s. “My aim here was not to expose racism and anti-Semitism,” he told The New York Times in October 2020. “The aim is to make people laugh, but we reveal the dangerous slide to authoritarianism.”

McKay’s and Cohen’s work, particularly in recent years, has injected a necessarily large dose of subversiveness into the mainstream. Their comedy has served as a translator of sorts, a way to explain the seemingly unexplainable state of society. While McKay’s movies have sought to expose the larger causes of our increasingly dystopian world, Cohen has tried to understand the people wrapped up in it. 

But their approach isn’t the only form of comedy that still works. Sometimes it helps to gain a little understanding; other times what’s needed is something as deranged as the world itself. 

The appeal of Conner O’Malley is hard to explain, but let’s start here: He once made Alex Jones uncomfortable.

While shooting a video for the faux news magazine Truth Hunters at Trump’s inauguration, O’Malley’s MAGA alter ego Mark Seevers sidled up to the infamous InfoWars host and asked whether he’s aware of “Kit Kat foot.” “It’s a rare genetic disorder where your feet become incredibly hard,” says O’Malley, “and the skin on the outside becomes thin.” All the eternally red-faced Jones could muster in response was, “All right, well, I’ll look into it.” 

Slowly, [Trump] will just fade into the fabric of all the other shit that’s made up this crappy American quilt, right?
Anthony Atamanuik

O’Malley, a writer for Late Night With Seth Meyers who’s occasionally popped up on the show to do an interpretative dance to the theme music from Charlie Rose, had by then spent hours at the future president’s rallies. There he played a terrifyingly realistic hardcore Trump supporter, down to the iridescent Oakley sunglasses and calls to forcibly remove protestors. What he was doing wasn’t a lazy impression; it was, he said later, “more of an embodiment” of the misplaced anger that Trump conjured. 

O’Malley’s most inspired work, however, has come in the years after Trump’s election. This borderline dystopian age has pushed his gonzo performance art in inexplicably funny directions. In 2019, he made a series of selfie videos showing him tweaking out as the world’s biggest Howard Schultz supporter. Last January, O’Malley released a nearly nine-minute, partially animated short film in which he traverses Manhattan’s newly opened Hudson Yards like it’s an open-world video game set in a soulless, colorless, capitalistic playground. Then in June 2020, O’Malley posted a video of himself riding his bicycle through New York. In the clip, which is scored to the late-era Metallica song “I Disappear,” he lampoons Mayor Bill de Blasio’s response to both COVID-19 and the anti-racism protests … by loudly serenading him. “I want to thank you, Bill, for Operation Midtown Bowl Rescue,” he says between violent coughs, “where you sent in the National Guard to protect midtown’s bowl restaurants from looters who are trying to break in there and steal edamame and carrot shavings.” 

At first glance, some of the bits may seem nonsensical. But look a little closer and there’s a thread connecting them: The way the country’s corporate and political class has exploited people is enough to drive an ordinary person to the brink. 

Tapping into and then absurdly reflecting rage back at audiences at a time when there’s a lot to be mad about can be viscerally funny. And social media has given comics, from stars to up-and-comers, a platform to vent that anger—and test out material. 

With clubs shut down due to the pandemic, funny people have, like Vine stars of old, taken to the internet. Named for performers who toil in front of a cellphone camera, front-facing comedy has exploded in popularity in 2020. Quick-hitting videos by comedians, many of whom are women, have amassed millions of views. The medium isn’t a financial gold mine for the vast majority of its participants, but it can lead to a big payday: Trump lip-syncer Sarah Cooper built such a large following in 2020 that she landed two TV deals.  

Comedic innovation hasn’t just been relegated to viral videos. In her new Netflix special, Nate: A One Man Show, Natalie Palamides plays the title character, a mustached, chest-hair-baring, giant-rubber-dick-exposing bro who’s far less emotionally mature than he thinks. By making people uneasy—Nate asks to feel up a woman in the crowd; Nate also brings an unsuspecting dude on stage and goads him into wrestling—the comedian pushes them to think about serious topics like consent and toxic masculinity. 

When deployed smartly, genuine shock is an effective weapon. Just ask the host of The Eric Andre Show, who spent the 2010s making his viewers uncomfortable by making his famous guests uncomfortable. (In 2016, T.I. bolted from the set after a pantless man appeared and a zombie emerged from the floor and grabbed the rapper’s leg.) “Comedy is not intellectual. It’s primal,” Andre told The Ringer’s Rob Harvilla last June, the week that his new stand-up special Legalize Everything premiered. “I’m not like, ‘OK, now, here’s what’s going on now in the world. These sets of topics are off-limits, and these sets of topics’—I’m not like a math teacher.” 

That’s not to say there isn’t room for smart, or intimate, or personal comedic stories. With billion-dollar budgets and an endless need for programming, streaming behemoths are always trying to find the next hot show. TV series like Issa Rae’s Insecure, Aidy Bryant’s Shrill, Ramy Youssef’s Ramy, Maya Erskine and Anna Konkle’s early 2000s period piece PEN15, the short-lived Lodge 49, and even Nick Kroll’s animated Big Mouth, have, in different ways, balanced humor, existential dread, and social commentary. 

Still, there’s something liberating about comedy that isn’t obsessed with reaching the zeitgeist. In spring 2019, as Saturday Night Live was doing things like pitting the casts of Avengers: Endgame and Game of Thrones against each other in Family Feud, the newly released Netflix sketch show I Think You Should Leave With Tim Robinson was staying away from most pop culture and political touchstones. The six-episode first season of Robinson’s series instead introduced uniquely absurd characters and put them in uniquely absurd situations. By blissfully giving its viewers a break from hyper-relevant jokes, a show that could be watched in less than two hours garnered an endless life span. 

Not only did ITYSL turn out to be a word-of-mouth smash hit, it also became a meme factory—because many of the sketches don’t play off specific events, they’re relatively timeless, and can be applied to a variety of real-world situations. In one sketch, someone drives his hot-dog-shaped car through a clothing store window. The driver, played by Robinson, refuses to cop to the crime, and then doubles down—despite the fact that he’s wearing a hot dog costume. The image of an incredulous Robinson has become a stand-in for any powerful person deflecting blame for something they did. Naturally, the “We’re all trying to find the guy who did this” meme hasn’t lost its utility—and probably never will. 

Soon, Donald Trump will vacate the White House. “Slowly, he will just fade into the fabric of all the other shit that’s made up this crappy American quilt, right?” says Anthony Atamanuik, whose Trump impression was the centerpiece of Comedy Central’s The President Show. “He’ll just be a part of that.” 

With the post-Trump world seemingly teetering on apocalypse, there doesn’t appear to be cause for much optimism. But there always will be a place for good comedy. The genre may be limping into the Joe Biden administration—theatrical movie comedy is nearly extinct, and the pandemic has crippled the stand-up industry—but it’s still breathing. Whether used as a statement against institutional rot, an outlet for rage, a method of processing trauma, or a silly way to reflect on life’s absurdities, it can both sting like hell and act as a salve. 

With the obligatory disclaimer that satire should never be confused with mass political action, laughter can be cathartic. After all, there’s no better method of diffusing American rage than reflecting it back at audiences in a way that turns its menace into caricature. 

These days, the most satisfying comedy manages to find levity in things that are fundamentally ugly. It’s podcasts like Doughboys, Nick Wiger and Mike Mitchell’s often critical love letter to the quintessential American establishment: the chain restaurant. It’s shows like Nathan for You, whose 201 finale, which involves a Bill Gates impersonator searching for his long-lost love, is at once disturbing, touching, and hilarious. It’s franchises like the male bonding laboratory Jackass, the cast of which has reunited to make a fourth movie. It’s the MacGruber TV show. It’s Conner O’Malley sweating profusely while holding a selfie stick. And it’s How to With John Wilson, each of its thousands of images like a misshapen blade of grass sprouting from New York’s broken concrete. 

In truth, Wilson isn’t a big fan of comedy. “I just feel like the comedy genre has some of the least funny stuff out there,” says the filmmaker, whose show was recently renewed for a second season. “I watch Inside Edition for the real funny stuff.” 

To Wilson, America’s surreality and salaciousness is morbidly hilarious on its own. It’s why he’s so interested in painstakingly chronicling it. “One of the most important parts of the work for me,” Wilson says, “is it’s actually shocking to see something even just a little different than what you’re used to.” And sometimes, he adds, “It happens to be funny.” 

Alan Siegel
Alan covers a mix of movies, music, TV, and general nostalgia. He lives in Los Angeles and is currently writing a book about ‘The Simpsons’ that will be published in 2025.

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