Anatomy Of A Sellout

Inside the mind of Colin Jost.

Anatomy Of A Sellout

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When I was 22 and newly living in New York City, I took a job at a tech startup. I was the second or third employee, depending on how you count the salesman who was hired before me and started after. It was my first real job out of college. My title was something like “content manager,” but you could say I was the head writer. The company offered a fairly complex, novel service at the intersection of law, finance, and social justice. They hired me to make it sound simple, essential. I handled web copy, content marketing, blogging, PR, pitching in with the sales team as needed, even proofreading the boss’s emails. My starting salary was $30,000, no benefits, with the promise of a raise when the company got its first round of funding.

My bosses were the company’s founders. There was Josh, a soft-spoken, smiley man in his 30s, a former reality show contestant who sold his first startup and married into wealth. His father-in-law, a retail magnate who occasionally showed up at the office, was one of the company’s angel investors. Josh had a JD and referred to himself as a lawyer, though he didn’t practice law. When he hired me, he said he was interested not just in what I could do for the company, but in shepherding the broader arc of my career. I sat in his office for most of my 10ish months there, giving him grammar tips and listening in on FaceTime calls with his young daughter. When he ordered a salad for lunch, he offered me the roll.

Then there was Dylan. Dylan was in his late 20s and the platonic ideal of a tech bro: blond hair, bulging muscles, Wharton grad (full ride, of course), never missed an opportunity to tell me how lucky I was to have a job writing. Like Josh, he sold his first company. Like Josh, he was weird about food. On one occasion he saw someone eating a bagel—was it me?—and said, “That’s one of the worst things you could eat.” This was an office where the cabinet was stocked with liquor and sweets were banned. Everyone stayed late on Friday nights to play board games, get drunk, and field whatever calls were still coming in.

I had never envisioned myself in this world. In undergrad I studied creative writing and medieval literature, expecting I would either stay in academia or somehow find a career in the arts. But the longer I stayed, the more natural it felt. I liked the company’s mission, and I was persuaded by my bosses’ conviction that it might someday make life better for millions of people. While my salary wasn’t much, it was more in a month than I’d ever had in my bank account. The work was pretty easy—for some reason, businesspeople tend to equate “competent writing” with “genius prose”—and allowed me to learn about law, finance, and the lives of people crushed by the justice system. I also ran our blog, which meant I had access to its metrics. I could watch in real time as thousands of people read the work I wrote or edited. It took barely a month for me to think, maybe this all makes sense. Maybe I should stick around a few years. Get that raise, climb the ladder, let my options vest—whatever that means—and see where it takes me. If I still want to go to grad school after that, at least I’ll have the money.

The feeling did not last. When the company got its first round of venture capital, Josh upped my salary a few grand and said it was all they could afford. This wasn’t the bargain, I thought to myself. I spent long meetings begging in vain to rewrite this or that manifesto he’d written in his awkward, stilted style, laden with clichés and jargon. Isn’t that what you hired me for? He and Dylan fired one of my coworkers for reasons I couldn’t abide. They hired more salespeople while increasing my workload. They sent me on wild snipe hunts, projects they were enthusiastic about one week and nixed the next. I never knew what they wanted, or if they knew what they wanted. I slowly got the sense that because I didn’t directly bring in sales, they saw little value in my work. At the same time, they acted like my ability to write meant I could do anything. I was simultaneously disposable and essential.

One day I was working on an office computer. In a shared folder, I found a profit and loss document drawn up for investors. The document included a spreadsheet detailing everyone’s salaries and options grants. Would you believe they could indeed afford more?

It all clicked. I could see myself as my bosses saw me. I was there to do whatever they wanted. I didn’t cost them enough to waste any time thinking about whether they really wanted it. If they changed their minds, they could just tell me to do the next thing, and the next.

I took a picture of the spreadsheet and sent it to some of my coworkers. A few days later, I quit.

When Colin Jost was 22, he joined the writing staff of Saturday Night Live. The year was 2005. He had recently graduated from Harvard, where he was a member of the storied Harvard Lampoon. At the time of his hiring he was writing for a Nickelodeon cartoon show. Prior to that, he worked as a journalist for the Staten Island Advance, covering local news in New York City, his home. He grew up in Staten Island and attended the Regis High School in Manhattan, a prestigious private academy that awards full-ride scholarships to young Catholic men with good grades. His father, the son of a manufacturing executive, was a high school teacher who previously worked in business. His mother, the daughter of an NYC firefighter, was the longtime FDNY Chief Medical Officer, who served on the ground during 9/11 and later advocated in Congress for first responders.

In his new memoir, A Very Punchable Face, Jost writes that his time as an SNL staff writer was the most fun he’ll ever have in his life. There’s a certain bleakness to this description: that time was over a decade ago. In 2009 he was promoted to writing supervisor, a sort of sub-managerial role whose exact responsibilities remain a mystery to him. He describes the job as “trying to write funny sketches and not freak out when Lorne asks you a direct question.” A few years later, he joined Seth Meyers as co-head writer. Though he stepped down for a couple seasons in 2015, this is the position he holds today, with Michael Che and Kent Sublette. He has worked at SNL for almost his entire adult life.

A Very Punchable Face is not a good book. Like many celebrities whose most interesting quality is their fame, Jost structures his memoir as a chronological series of chapters centered around a particular story or theme. That time I went to Harvard. That time I went to Copenhagen with my colleagues, bought expensive clothes, went clubbing, made out with a girl, then made out with her sister. That time I went surfing with Jimmy Buffett. That time I hosted the Emmys, and people didn’t like it, but what they don’t understand is that it’s actually a very difficult job where the producers don’t let you do what you want, and also I’d do it again if they asked. All those times I shit my pants. There’s no overarching narrative, except maybe a few unintentional ones, and certainly no central moral inquiry. While he frequently offers self-deprecating commentary about how awkward he is—flubbing things with a girl, embarrassing himself in an interview, having a punchable face—the book mostly functions as a chronicle of his cool, fun life.

It’s very strange. For a man who at 22 entered a career and social stratum many desire but few attain, Jost offers little in the way of introspection. Or even self-awareness. In the first chapter, “Finding My Voice,” he recalls how he didn’t speak until the age of four. This is framed as a defining quirk: Even today, he writes, he gets nervous in conversation, mutters “Uhhhh” as he figures out what to say, and dreads incoming phone calls. The reader would be forgiven for observing that these are normal human traits. Later he devotes an entire chapter to insulting two Google employees, by name, over what truly sounds like a misunderstanding. In the summer of 2016, Jost visited the company’s New York office to test its VR equipment for a potential collaboration. Once in the VR program, he found himself on a diving platform. The engineer overseeing everything told him to jump, apparently not grasping that Jost thought he had to take a real physical leap. Which he did. Into a metal table, busting up his knee and torso. He went to the hospital to get stitches, and had to use crutches during what he says was his first week off in two years. (I’m not sure how to square this assertion with SNL’s frequent hiatuses; maybe he’s including standup, though he says elsewhere that he took time off from standup in the summer of 2015.)

There’s nothing particularly funny or illuminating about this story. He fills it with quippy asides, but it still reads as a straightforwardly angry diatribe against a random guy who pissed him off four years ago. Jost describes the engineer as a “full idiot,” a “moron,” a “doofus,” a “fucking asshole,” and a “fucking dickface.” He calls the engineer’s manager, whom he summoned for an apology, an “ass-for-brains” simply because the guy qualified his apology by defending the engineer. Jost complains that Google didn’t pay his medical bills or “offer anything beyond an email to my agent saying, effectively, ‘Sorry, please don’t sue us,’” which he pointedly notes he did not do. Then he wraps it all up as just another story about his own foolishness. “Because only I could visit a virtual space and then have to go to a real-life hospital.”

These passages illustrate what makes A Very Punchable Face an interesting document if not a compelling memoir. For all his ponderous self-indulgence, Jost manages to tell a completely legible story about what it takes to succeed in late night comedy. My sincere impression is that he tells this story unwittingly. It lurks in the book’s subtext, emerging piecemeal through lighthearted anecdotes about what Jost does not seem to recognize as a horrid work environment, an abusive boss, and decisions it is only possible to make—and then look back on nostalgically—if you have no conscience. But the story itself is unmistakeable. It’s the story of a sellout. Once upon a time, a young man got sucked into a machine too big for him to comprehend. It offered everything he wanted: fame, wealth, friends, laughter, a creative and glamorous life. All the machine asked in return was total submission. He had to become a cog.

It is worth remembering that Colin Jost is, by every measure, wildly successful. He got hired at SNL off his second packet submission when he was 22. (He submitted his first packet midseason, when the show wasn’t hiring.) He wrote eight sketches that aired in his first season, an impressive feat for a freshman, and rose steadily through the ranks to become head writer. In that position he writes cold opens and guest monologues, while shepherding other sketches to air each week and influencing the makeup of SNL’s writing staff each year. He also anchors the show’s topical news segment, Weekend Update, with Michael Che. At 38 years old, he holds considerable power at TV’s biggest variety comedy institution, a show that transforms unknown comedians into Hollywood elites.

So what are his politics? You have to have politics to write political comedy, don’t you? What does Colin Jost believe?

Funny you should ask. He doesn’t really say. Oh, he mentions in his introduction that he’s “voted Democrat in every single election for every office, even the weird ones like 'State Supreme Court Bailiff,' where half the names could be fake and no one would even know." (Then, in a footnote: "I once voted for a judge because his last name was 'Ice' and I just thought that was awesome.") He also makes clear that his perfunctory loyalty to Democrats at the ballot box does not translate into support for left-wing policies. In his chapter on his favorite sketches he’s written—yes, an entire chapter—Jost fondly recalls a confused 2014 piece lampooning Barack Obama:

It was hard to write cold opens in the Obama era because he wasn't on television every day attacking American companies or re-tweeting white supremacists. But he did use an executive order to circumvent Congress on immigration, and it seemed like "Schoolhouse Rock" was a way to make that subject a little more bearable. (With cold opens, anything that's not a president talking at a desk is a win in my book.)

First Kenan appears as a cartoon "Bill" that is working its way through Congress. Then Obama pushes the bill down the Capitol steps and introduces "An Executive Order."

Bobby walks in smoking, and his only line was: "I'M AN EXECUTIVE ORDER / AND I PRETTY MUCH JUST HAPPEN!"

The whole sketch was three and a half minutes long and it was one of the only clean hits on Obama that entire season.

Here’s what Jost doesn’t mention about that executive order, which was actually an executive action. It offered temporary legal status to millions of undocumented immigrants, shielding them from deportation. Republicans indeed decried it as an abuse of power, though the previous two Republican presidents both issued comparable orders to protect immigrants left behind by Congressional reform. Jost’s “clean hit” on Obama implied the action was unprecedented and unconstitutional, giving rhetorical fodder to anti-immigrant politicians like Ted Cruz. That’s an odd thing to be proud of if your problem with Trump is that he boosts white supremacists. The sketch also argued that “people clearly don’t want this,” when in fact a majority of 2012 midterm voters opposed the deportation of undocumented immigrants. This raises a question that I suspect answers itself: which “people” was Jost referring to?

A Very Punchable Face is full of revealing little moments like this. Elsewhere in that chapter, he writes that he initially wasn’t sure SNL should cover Brett Kavanaugh’s nomination to the Supreme Court, because it was “a super delicate subject that was painful for a lot of people.” (Are other political subjects, like immigration, not painful for a lot of people?) What pushed him over the edge was Kavanaugh’s opening statement at his confirmation hearing, which was so aggressive “that I thought, on a basic level, How is this person going to be an impartial judge?

Not his judicial history, not the rape allegations—it was Kavanaugh’s performance that inspired Jost to question his judgment. Compare this with the fondness toward George W. Bush he expresses in his reflection on 2018’s “George W. Bush Cold Open”:

After a year of writing for Trump, writing for George W. Bush again seemed so much sillier and happier. You might think W. was a terrible president, but it's hard to argue that he's not a decent man who cares a lot more about America than our current president. And using him to put Trump in perspective was a lot of fun.

Now contrast that with the text of the sketch he’s talking about, which, again, he wrote:

According to a new poll, my approval is at an all-time high. That’s right. Donny Q. Trump came in and suddenly I’m looking pretty sweet by comparison… A lot of people are saying “Man, I wish George W. Bush was still our president right about now.” So I just wanted to address my fellow Americans tonight and remind you guys that I was really bad. Like, historically not good… Please do not look back at my presidency and think, “This is how we do it.” Don’t forget, we’re still in two different wars that I started. Hey, what has two thumbs and created ISIS? This guy.

Like the show he works for, Jost conceives of politics synecdochically: as a conflict between individual politicians reducible to their superficial personality traits. He occasionally acknowledges the destructive role of those politicians’ power, but otherwise does not seem to notice. (At least, not enough to remember what he wrote two years ago.) In a chapter defending Lorne Michaels’ decision to book Donald Trump, he insists that no one in late 2015 took Trump all that seriously. Everyone knew he was a Democrat (never mind that he was running as a Republican on a reactionary, xenophobic platform), and no one expected he would do the things he was saying (was the saying part not bad enough?). Plus, Trump is charming in person. He didn’t come with a security detail, and when he first walked into Jost’s office he complimented Jost’s looks. “By the end of the week,” Jost writes, “I think most people at our show thought, Huh. This guy isn’t a monster after all.

Two pages later, he argues that it was unfair to say SNL “humanized” Trump, because Trump had already been on loads of TV shows. “He was very, very human.”

Okay, I will now switch from “show” to “tell.” Colin Jost is not a bright guy. This is evident in everything he says and does, from admitting his staff was so stupid they got charmed by Donald Trump to the time he made a queerphobic joke on Weekend Update and defended it on Twitter, basically suggesting that pronouns cost Democrats the White House. You don’t have to read his memoir to see it. You just have to watch SNL. What his memoir does reveal are the ways his character is inseparable from his success. His naïveté, his credulity, his elitism, his shallow view of politics—these are what make him good at his job. To understand why, we have to reexamine what exactly that job is.

There’s one simple reason SNL is such a boring unfunny parade of endlessly referential humor and incoherent politics stuffed into the slackened mouths of whatever celebrities NBC shipped in to stare blankly off-set until the “Applause” sign flickers off and an audience of agents and Pete Davidson stans falls to a perfect hush for another joke about Trump’s orange face. His name is Lorne Michaels.

SNL’s boss, brain, heart, soul, and driving creative force is a 75-year-old man obsessed with fame and power. This, too, takes no special insight to see. It’s been out in the open for decades. An SNL insider told New York Magazine in 1995 that Michaels has “always wanted to be admired—revered, even.” Alumnus Julia Sweeney lamented that he was often too busy tending to his famous friends (and his coterie of young female assistants) to pay her any mind. Taran Killam recalled in 2018 that SNL’s 40th anniversary show, when all the celebrities Michaels anointed came back to celebrate him, was such a “potent overwhelming boost of a ‘this is your life’ experience” that afterward he became “very impatient” with the cast of B-listers 40 years younger than him. Jost, who’s worked with Michaels for 16 years, describes him as a fickle, angry boss who extracts his workers’ fealty by suspending them in a state of perpetual fear. Under his leadership, SNL’s chief function is to flatter its hosts, even if they’re running for president on a “Mexicans are rapists” platform. “Once a host arrives—even one you’re ambivalent about—you do your best to make them look good,” Jost writes. “Or at least minimize how bad they make you look.”

SNL isn’t just a comedy show. It’s a massive PR apparatus benefiting its celebrity guests. Michaels runs that apparatus and handpicks those beneficiaries; he also picks SNL’s writers, cast members, and the sketches that get produced. His longstanding relationship with NBC provides comfortable autonomy, and his authority over the show is basically unilateral. On the one hand this would seem to make sense: he’s spent his entire life in comedy. Logically he must have razor-sharp instincts about what works. On the other hand, this makes no sense at all. He’s spent his entire life in comedy. The man is separated by decades, millions of dollars, and perverse financial incentives from the lived experiences of his audience. His friends are all movie stars and producers and politicians and executives, people who walk the same elite corridors. How would he know what normal people care about, what normal people think? How would he know what’s funny?

In theory, people like Jost serve as a conduit between Michaels and the younger voices on SNL’s writing staff. In practice they exist to exert his will. Part of his job, Jost writes, is to help select which sketches make it past the table read. Often this means advocating for riskier sketches that Michaels doesn’t like. This is a perilous endeavor, because if Michaels lets one of those sketches air and still doesn’t like it, he’s liable to get so angry that he doesn’t rehire the writer next season. Jost keeps mum about how many writers have suffered this fate. Still, he says the stress of the job was so taxing that he once had a panic attack on his way to Michaels’ office after the table-read. What he ultimately learned was that sometimes it’s best for his writers if he doesn’t advocate for their work.

The picture Jost paints of Michaels’ workplace is deeply disturbing. Maybe I am underestimating his savvy, but he seems completely naive to the toxic management style he describes at length. After his first season hosting Weekend Update, he spent the summer wondering whether he’d be invited back. Eventually Michaels informed him through a producer that he had to re-audition for the role. The news filled him with anxiety, but after a few days writing and riffing with the other contenders he felt better. On the day of the audition, Michaels nixed a scheduled in-studio rehearsal at the last minute, sending them straight to the on-camera audition. “I remember that halfway through the auditions, I was so angry at Lorne for not letting us rehearse that I actually got better,” Jost writes. “That may have saved my audition. But it was still a demoralizing exercise… To this day, I don’t know what Lorne and the producers wanted from those auditions, or what they learned from them. I just know it felt like I’d failed.”

A week later he got a call from his manager, who heard he got rehired with Michael Che. Jost hadn’t heard anything from SNL, and his manager wouldn’t tell him where the information came from. Then he received a call from an SNL producer furious that he told his manager the news. “Lorne is really mad about this,” the producer said. “I don’t know what’s going to happen now.” Jost eventually learned that his manager’s intel was accurate, though he still couldn’t trust it fully. “Until you’re actually on the air, you have no idea if Lorne will change his mind and give it to someone else.”

I don’t see any other way of looking at this. Jost is describing emotional abuse. Michaels dangled the possibility of unemployment in front of his loyal staffer of nine years, using a combination of distance and anger that kept Jost demoralized, insecure, and in a state of uncertainty that persists to this day. Jost has since internalized this treatment as good for him, actually, just like it’s sometimes best for his writers if they don’t fight too hard for a sketch they believe in. This echoes what former cast members told New York 25 years ago:

“Lorne wants people to feel insecure,” says an ex–cast member. “It’s the same techniques cults use—they keep you up for hours, they never let you know that you’re okay, and they always make you think that your spot could be taken at any moment by someone else.”

Michaels also sends messages through the Brillstein-Grey Company. The powerhouse Hollywood management-and-production team, founded by one of Michaels’s closest friends, Bernie Brillstein, handles eight of the fourteen SNL cast members as well as its executive producer. The connection makes spinning off movies much easier. “To your face, Lorne always wants to be the hero and Santa Claus. But if you try to do a movie that Lorne’s not producing, Brillstein-Grey will let you know he’s not happy,” says an ex–SNL star who’s had it happen to him. “Brillstein lets you know you’re in the doghouse. Your sketches don’t get on, or you get on in the last five minutes of the show

Put these pieces together and you get a boss whose management style is Don’t make me mad or I’ll fire you, and by the way, pretty much everything makes me mad. Now we can see that Jost’s job is not really to make comedy. It’s to keep Lorne happy. This framework explains everything about SNL. Of course the sketches are rarely funny; risk-taking is punishable by exile. Of course the satire is toothless; it’s written by people afraid of their boss. Of course the show takes every opportunity to flatter power; the boss only cares about his friends, and his friends are other bosses.

The last time I saw him, Josh took me to the office he and Dylan just leased across the street, a massive open space in the upper levels of a Financial District low-rise. It had high ceilings and an enormous patio lined by leafy plants. The last tenant was still clearing out, and we sat at one of the tables they left behind. I asked Josh for a raise, something more in line with the cost of living in New York City. I knew he’d say no, but I felt I had to hear it. When he turned me down, I said it was time for me to pursue opportunities more aligned with my interests. He asked: “Just to be clear, you’re saying it’s not me, it’s you?”

I don’t remember why I didn’t bring up the spreadsheet. Maybe I felt guilty about snooping, or I thought it would be unwise to burn the bridge. Probably I was just young, and confused, and I didn’t yet have the vocabulary to understand what was happening. I could sense that I had come up against something that repulsed me. But I was not merely repulsed. I was humiliated to think how easily I’d been fooled, and I was ashamed to recall how eagerly I participated in my own exploitation. I didn’t know how to reconcile Josh’s warmth and mentorship—was it warmth? Was it mentorship?—with the cold, obvious truth that he didn’t care about me. I existed to make his life easier.

He asked if I would please, before I left, write a document detailing everything I did and knew, so he could give it to my replacement.

I don’t know Colin Jost. My understanding of the man is based on his work and the few stories he chose to make public in his memoir. I don’t know if he entered SNL with beliefs, principles, and integrity, only to compromise them bit by bit as he ascended the ranks. Or if he entered as a blank slate, perfectly suited to do whatever the job required because he had nothing to give up.

What I do know is that SNL is designed to extinguish the beliefs, principles, and integrity of its workers, and that Lorne Michaels personally executes this design. This is the unintended message of Jost’s memoir: that you cannot get to his position if you are unwilling to sacrifice your conscience. Late in the book, he describes a series of nettlesome notes from one of the show’s advertisers, Volkswagen. The auto giant repeatedly told him to nix jokes about Hitler and Nazi Germany, afraid they’d remind people of Volkswagen, which was founded in the Third Reich. Jost balked at the idea that anyone would make this connection. Some time later, the Volkswagen emissions scandal came to light. Jost and his colleagues wrote and produced a commercial parody reminding viewers that Volkswagen was founded “on the vision and values of Adolf Hitler.” From his description, it sounds like honest, funny, truth-to-power comedy that told a major corporation to go fuck itself. But NBC was about to close a major ad deal with Volkswagen, “so we were never allowed to air it.”

Jost relates this story with no trace of irony or regret. He does not seem bothered that his sponsor perpetrated massive fraud, that his work lampooning this fraud was censored out of deference to the sponsor, or that his employer continued taking (and paying him with) the sponsor’s money after its fraud came to light. He concludes with a joke: “All that said, I’ve heard the 2020 Volkswagen Jetta is remarkably fuel-efficient. And it was just rated ‘Best in its Class’ by JD White Power and Associates.”

Do you feel sorry for him? I can’t tell if I do. By his own account, he’s an amoral, opportunistic writer. When Republicans drummed up another Obama scandal, Jost leapt to adopt their talking points—never mind that it meant advocating for mass deportations. When Trump hosted, he pitched an ad for “‘Rosetta Stone Mexican,’ which would teach you low-level racist phrases you could say to someone who was Mexican. Like: ‘You’re gonna pay for that wall.’ ‘Yes, you are.’ ‘Yes, usted will.’” If he believed in 2018 that it was foolish to pine for George W. Bush, he doesn’t anymore. There’s nothing in there. The man’s a hack.

And yet. By his own account, he has been shaped in some capacity by the cruel manipulations of a heartless boss, an extremely powerful man who, Jost says, does not like his employees to leave of their own volition. Which Jost hasn’t. He’s been at SNL since he was 22. He repeats throughout the memoir that it’s the perfect workplace for young people with no families. They have everything to give it. Apparently that’s exactly what SNL takes.

The question I ask myself is: If Josh offered me more money, let’s say a lot more money, would I have stayed?

No. Definitely not. Maybe, though?

Perhaps a little while, just long enough to find something better.

But what if, in that little while, I discovered that I liked the money?

What if it made up for everything I didn’t like?

How far would I have gone?

Here’s the most important thing about Colin Jost. Comedy is full of Colin Josts. SNL especially is full of Colin Josts. Its stars come and go, but many of the influential figures behind the scenes—almost all white men—have been there for decades. Steve Higgins has been there since the mid-90s. Jim Downey, whom Adam McKay once said is a right-winger and friend of Ann Coulter, crafted the show’s political material for more than 30 years. Mike Shoemaker was there from the mid-‘80s until he hopped over to Late Night With Jimmy Fallon in 2009, then Late Night With Seth Meyers in 2014. Do you think these men came up under better, kinder conditions than Jost? There’s no way. I wonder what their success cost. What did they give up of themselves, and what did they take from others?

You may remember a brief hubbub last year over an article in MEL. It quoted a late night writer who called the form “a dumb factory of lazy ideas.” As I wrote at the time, the piece was criticized by other late night writers and workers. They felt it was unfair to the hard work they put in, and that it set an impossibly high bar for political comedy.

As I read A Very Punchable Face, my mind drifted to two writers’ responses to the MEL piece. At one point, Sean O’Connor, who would go on to become head writer of Lights Out with David Spade and A Little Late with Lilly Singh, wrote on Twitter that “all political humor sucks,” from Lenny Bruce to Bill Hicks. Ian Karmel, James Corden’s head writer, wrote that he was “Trying to figure out the perfect joke to get Trump arrested and get sent to the Hague.” In both cases, the critique was that it’s unfair to expect much of political comedy, which is ultimately just that: comedy.

The more I thought about these comments, the more astonished I became at what they represented: the internalization by professional comedy writers of their own worthlessness. All political humor sucks? Jokes can’t make a difference? Aren’t you supposed to be the ones who believe in this shit?

I’m as cynical as anyone, but even I believe that when you tell truth to power, sometimes power buckles. Powerful people are some of the weakest motherfuckers alive! Look at Michelle Wolf at the White House Correspondents’ Dinner; look at Jon Stewart on Crossfire; look at Pete Davidson making fun of Dan Crenshaw; look at Bret Stephens’ response to a guy calling him a bedbug. Hell, look at what happens when anyone criticizes Michael Che. If nothing else, direct broadsides against the powerful reliably cause them to reveal their own fragility. Power relies on the appearance of legitimacy, and that appearance relies on a tenuous social contract in which everyone agrees not to say it’s just that: an appearance. Maybe comedy can’t tear down the castle, but it can open a crack in the walls. If jokes posed no threat, Volkswagen wouldn’t tell Colin Jost to rewrite his jokes.

And that’s the whole ballgame, isn’t it? Shows like SNL enforce that contract by manufacturing comedians who don’t believe in comedy. They’ll call you Nazis one day and take your money the next. No sweat. After all, it’s one of the only honest jobs in the business.


It was a pleasure to quit. I’ve enjoyed that pleasure a few times since. On each occasion I walked outside and felt my old life vanish behind me. Look, here I am. It’s a warm spring day. All that grief? It was just people in a room, and I’m not in the room anymore. I’m someone else.

I hope Colin Jost has that pleasure someday. I wonder who he’ll become.