What I Learned in the Late-Night Joke Mines

Current and former writers reflect on trying to wring humor from the Trump administration.

Photo-Illustration: Vulture and Photos: Andrew Lipovsky/NBC; Courtesy of CBS; Courtesy of HBO; TBS/Youtube; Courtesy of Comedy Central
Photo-Illustration: Vulture and Photos: Andrew Lipovsky/NBC; Courtesy of CBS; Courtesy of HBO; TBS/Youtube; Courtesy of Comedy Central

“Can anyone tell me that Stephen Colbert, or Trevor Noah, or anyone doing an impression of Trump is really as funny as Trump? I don’t think so,” a writer, who worked on a popular late-night show all four years of Donald Trump’s presidency, tells me over the phone. “Donald Trump as the president is like a sketch that I would have written for UCB’s Sketch 101 class in 2005.”

It’s a refrain we’ve heard over and over from writers, comedians, and critics: Trump is already a parody, so attempting to parody him is hopeless. For late-night writers — whose job requires them to wring comedy out of an absurd and often horrifying news cycle, every single day — figuring out how to joke about Trump became the core challenge. Their struggle to do this was revealed in everything the shows’ hosts did onscreen: They played with Trump’s hair. They attempted to impersonate him. They got other people to do jokes for them. They confronted controversial conservative figures. They half-apologized for kissing Sean Spicer. They delivered emotional pleas for change. They reflected on senseless tragedies. They cried. And, on several occasions, they all came up with the same joke.

Ahead of Biden’s inauguration, Vulture spoke with multiple late-night writers who either still work or previously worked for Stephen Colbert, Jimmy Fallon, Trevor Noah, Jimmy Kimmel, Samantha Bee, Jim Jefferies, and John Oliver about what it was like inside the Trump-joke trenches — and how they see the next administration affecting their jobs. While some writers offered comments on the record, the majority spoke on the condition of anonymity. In order to protect the latter, Vulture has decided to keep all responses anonymous.

In every interview, two themes emerged: Writing Trump jokes sucks, and those who are still working in late night are exhausted. Here’s what else they had to say.

We didn’t take Trump seriously enough at first.

My colleagues and I had a lingering, nagging sense of culpability. We became part of this nightmare recursive loop of Trump content being pumped into people’s houses. So I definitely worried: If I just stop writing about him, will he go away? I guess we’ll never know.

At the time, it was still considered inconceivable that he would be the nominee, let alone the president. So he was a perfect late-night target in the same way these larger-than-life clownish public figures are late-night targets — you just don’t think that they’ll be the commander-in-chief of the armed forces one day. When he was inaugurated, I remember my office mate and I looked at each other, and it was sort of like, What hell hath we wrought? 

Occasionally, you had to break news.

There was always this breathless pace of trying to keep up with the news. Sometimes we even held the monologue, or held jokes, or put the show on hold for 30 minutes when there was a late breaking story, and we would be the ones to break that news to the audience. That was always tricky, because if it’s a serious story, the audience isn’t going to laugh when they’re still thinking about some crazy thing that we just told them happened.

The shows’ goals were sometimes unclear.

Our host has explicitly told us, “This show is not a force for change. We’re just a comedy show.” And I think he means that when he says it — he is a genuinely good guy. But then you look at some of the heartfelt sentiments he’s expressed, and it’s like, Hmmm. Okay. Seems a little serious for the show “not being a force for change.”

Everyone had the same joke.

Back in the days of The Daily Show, Jon Stewart was doing something different. The show was about media criticism and how people were covering George W. Bush and really having fun with the “gotcha” clips of “Well, Bush said this at his speech yesterday, but a year ago he said this.” Playing those things off each other and pointing out that kind of hypocrisy, that felt fresh to me. And then, honestly, I think Twitter is the worst invention of modern times. That ruined it because everyone was doing it, and it was all the same thing. It’s not effective anymore — everybody sees the same clip and the same quote and misinterprets the same headlines. That’s what I wanted to avoid. Vulture did a roundup of late-night hosts who all told the same joke. I was like, I never want to tell one of these jokes.

It was hard to find “the line.”

Jim Jefferies is very much on the side of I don’t care what anyone thinks, and I am going to say what I want to, and fuck everybody else. During the child separations, we had a character of a kid in a cage onstage. The original premise for the bit was a game show called Who’s the Real Victim?, which was poking fun at people who had done awful things blaming cancel culture for the consequences. In the final bit, Jim wins a trip to a family-detention center so he can teach immigrant kids what real struggle is. That’s when a game-show model pulls a blanket off a cage, and we had a kid that was in this cage. He made multiple appearances on the show as Cage Kid. Every time, it got that uncomfortable laughter — that gasp of I don’t know if I should be laughing at this.

The staff were watching rehearsal, and they were like, Oh my God, we can’t. This is death. We can’t do this. This is terrible. And we did it, and it was funny and one of the more memorable segments from the show. After that, Cage Kid became this running gag as a way for the show to acknowledge that we’d never really do a sober deep dive on family separations but we could still say, “Hey, remember this terrible thing is still happening.” In that way, it was kind of a cheat — we got credit for talking about it without really talking about it. Every time we had that kid on, I always felt that Uh oh, wait — is this funny? I think the message of the joke was a little muddy, like, What are we saying about this? Is it just funny that we’re seeing a kid in a cage, or are we really saying something here? And in that case, the joke was really just the audacity of doing it. There wasn’t much beyond it other than Oh my God, I can’t believe they did that.

It often felt like a “liberal circle jerk.”

It seems to be a loose rule that late-night writers are more progressive than hosts, showrunners, and executive producers. Writers get compensated extremely well, but they’re still way more likely to actually know people who are hurting than the same circle of mostly white multimillionaire showrunners and producers who float among the same five shows. When you’ve been crazy rich for over a decade, and so have a lot of your friends, it’s difficult for a lot of these hosts to have any conception of what people are hungry for in the real world.

We’re applauding late-night hosts for using their platforms and multimillion-dollar salaries to sob about the state of our nation every other night. Jimmy Kimmel and Stephen Colbert are probably the worst offenders here. The latter is sometimes crying on TV about things nobody else is even that upset about. Trump’s first speech from the White House after Election Night was, predictably, full of lies and fascist propaganda. Colbert wore all black in mourning and stood up to deliver the monologue for the first time since March. Just in case anyone watching had recently suffered a blow to the head and couldn’t detect that symbolism, he made sure to explain, through tears, why he was doing it.

It’s not that I don’t think his tears were sincere. It’s that they were wasted on something so stupid, and they’re the only ones he chose to broadcast. Where were those tears for George Floyd and every Black American murdered or injured during the Black Lives Matter protests? Where were those tears for the quarter million Americans who have died of COVID? And above all, why would anyone want tears from a comedy show in the first place? Have all of our brains collectively broken this badly? Much of late night devolved into this Aaron Sorkin–ified liberal circle jerk. It’s not productive, it’s not impressive, and it’s definitely not comedy.

If the goal is to keep preaching to a mostly white, middle-aged, upper-­middle-class audience, then sure, don’t change. Just wait for the next fascist to take office and continue this masturbatory rage ouroboros. There’s clearly good money in it.

The competition was fierce.

I didn’t watch Colbert for a long time because I was bitter that they were kicking our butt on Jimmy Fallon’s show by so much. I’d go, Oh my God, we have the greatest monologue today, and it was. Then I’d go home and watch Colbert, and I was like, What do we have to do? What is going on here? I’d watched some of Stephen’s “at home” shows, and I was really like, Man, this is how you do it. ­Colbert’s jokes are targeting Trump and only Trump, but they’re good jokes. They’re really well crafted. The same thing with Seth Meyers.

The audience could be overly sincere.

Personally, I never thought I would write for this show. I feel like whatever I’m doing now, it doesn’t really feel like comedy. I feel like everybody is trying to have fun with this thing, but it’s just an awful thing. It’s hard to provide escapism, because I feel like, at least with our show, people just want to turn to something that will confirm their biases.

I just feel like we’re very hamstrung by the audience and what the audience wants. You always have to be making a point about something serious, and you always have to be on the right side. We can’t really be ironic. There was a New York Times article I thought was really spot-on about how now the Republicans are the ones who can be sarcastic and say what they don’t mean, and liberals have to be sincere all the time, otherwise you lose people. You don’t want to lose the audience you’ve built up. I think there’s just going to be some light ribbing of the Biden administration. We’re going to set our sights on the people who say obnoxious, sexist, racist things about Kamala Harris. We’re going to set our sights on Fox News and the machine against Biden and Harris. That’s what the late-night show I work on was pre-Trump: just criticism of Hannity and all the disgusting things people say.

I actually think the audience is the problem. I think that when Trump was president, people got really scared and turned to us for comfort, and didn’t want anything acidic or particularly challenging. Like I said, they want their biases confirmed. We played with it; we didn’t play against it. So it’s hard to break out of the echo chamber.

I don’t think we’re going to necessarily give Biden a total pass, but I still think I’d use kid gloves. There’s a couple of reasons Biden is funny, but the primary thing is that he’s very, very old, and that’s ridiculous. He’s out of touch. There was also the whole thing when he was facing those sexual-assault allegations; we didn’t do a single thing about that. This was a major story, and it’s just like, We’re not going after that. I sound like I’m a conservative, but I’m not. Sometimes, I’m like, Are we a propa­ganda machine? I don’t know. There’s a weird double standard.

Trump was too easy a target.

For the first time in four years, ­writers’ rooms are going to have a political divide within them. I don’t know how that will reflect on TV. In my room, there’s an even divide between people who are very far left, people who are more centrist, and some people who don’t have a strong political take and just want to do comedy. It’s easy for all those people to align when you have Trump in office and he fucking sucks and everyone hates him. Now, people in the room will have different takes: Biden sucks versus Biden’s doing the best he can versus no opinion. The host ultimately dictates the story the show tells and the angle it takes, so if half his room disagrees with him, what does that look like?

Trump was certainly a convenient target for subjects it might be difficult for hosts to talk about otherwise. Police brutality and Black Lives Matter marches aren’t gonna stop. The wealth gap will increase. Immigration policy will almost certainly not get better. We’re about to see an unprecedented eviction crisis under a Biden administration; how are we gonna write our little yuks about that when we can’t blame Trump for all of it? Very few late-night hosts are equipped to deal with those things, so we’ll see how it goes.

One thing that stood out to me was this year’s DNC. At that point, we were all working remotely, but even on Slack it was more fun joking around with the other writers in the digital room. I specifically remember thinking during the event, Oh, this is better and easier to write for. I don’t personally love the Democratic Party, but it was definitely more fun to write jokes about that convention than the Republican convention the following week. I don’t know if it’s because of Trump or just a natural consequence of writing jokes about anything for four years straight, but having the two conventions back-to-back certainly highlighted the comedic potential of one and the same old shit of the other. You know, the banality of evil.

And mocking him felt pointless.

I don’t remember the last time I laughed at a Trump joke on any show, including my own. That’s not an indictment of my show or the host or the writers, it’s just that I can’t find the humor in this anymore. I can write jokes and hope that someone else finds the humor, but none of it’s funny to me. And it was useless. It doesn’t hurt him, it doesn’t do anything. It doesn’t change anyone’s mind.

But live audiences only responded to Trump jokes.

We tried to do silly non-Trump jokes. We rehearsed in front of a live audience, but when we were done with the Trump jokes, the energy just died. It was just clear that, for whatever reason, other stuff was just not going to fly. So most of the monologue ended up being 90 percent Trump jokes. It’s like an addiction: That’s all people wanted.

That infected other jokes too.

It felt like a lot of the time Trump was steering the ship. It’s not like we weren’t conscious of that after a while where we were like, “We’re not going to mention Trump unless we have to mention Trump.” But it’s kind of crazy, because let’s say that there’s some story about a panda rescuing someone or something. It’s so easy to make a Trump joke about that because, from the audience’s point of view, it’s so unexpected. So it’s very easy for even non-Trump stories to have a Trump punchline, because it’s this kind of shorthand. Then it becomes like, Oh my God, this is just, like, The Trump Show.

Late night gave Trump what he wanted.

It’s frustrating because you know the one thing he wants more than anything is attention, and that’s what the world (including us) has been giving him. Every day, whether on TV or just in our personal lives, so many conversations begin with “Did you hear what Trump did?” It’s the narcissist’s dream to have everyone thinking and talking about him constantly, and he manipulated us into doing that. We rewarded his abuse by giving him exactly what he wanted.

It stopped being fun. Really quickly.

It’s like drinking poison: How much poison can I make myself drink today? Maybe I can filter out some of the poison, and they can hear the news through this comedic perspective. But after a while, you get tired of drinking poison every day. I think that’s why a lot of people start out in late night and then very wisely move on to other things — they get to running a sitcom or something like that. I don’t have the gene for that, unfortunately. I just always wanted to do late-night stuff. I still don’t really want to do anything else. So I’m probably just going to keep poisoning myself until I drop dead, or until I age out of employability.

But joking about Trump sometimes prevented you from crying.

Approaching it as a joke writer was a way to stay anesthetized to what was happening. So as much as it was torture to have this low dose of it every day, it prevented us from having a day where we just walked around crying.

Not every host found the “right” way to tackle Trump.

Jimmy Fallon would tell the audience, “The goal of the show is to get you relaxed and sleepy before bedtime.” It was kind of a self-deprecating joke, but it was also true. The problem is when you need a little levity and you’re talking about Trump. The show was looking for a solution, but it might be that there just was no answer for the right way for Jimmy to be funny and relevant during the Trump years.

The problems went beyond the writing.

There should also be a total overhaul when it comes to considering which guests to book. Why is fucking Rahm Emanuel making the circuit, straight up lying about Bernie Sanders’s gun record? Why was Chris Christie a regular guest on The Late Show? How is that any better than Rick Santorum getting a CNN gig? It’s bad enough that these people get booked on regular news shows, but there’s no mechanism in place for late-night shows to issue retractions or to hold disingenuous politicians’ feet to the fire if they lie. They’re not those kind of shows — so stop booking people who famously always lie.

Complacency during Biden’s presidency is a concern.

The end of Trump’s presidency is probably a relief to a lot of the more traditional late-night hosts. Not only can they stop focusing on Trump, but so can their audiences. If you’re a fan of The Tonight Show or The Late Late Show, it’s going to be a lot easier to enjoy pre-2016 fun games and sketches with celebrities when the audience isn’t thinking about the latest horror to occur. On the flip side, there’s the chance that we all move too far in the other direction of, “Everyone is now tired of politics. We solved it!”

And it’s unclear if audiences will stick around.

When people find out who I write for now, they always say something to the effect of, “What’s he gonna do now that Trump is gone?” I’m not worried about our ability to write funny, good jokes, but there is some question of whether our audience will stick around if we’re not just dunking on Trump every night. Our YouTube comments are insane — just like, “President RUMP is a threat to Democracy! Call your senators! Individual Number One must be STOPPED!!!!” So the audience definitely comes to our show for a certain thing, and we’ll have to see if they’re still interested if that guy they hate is gone.

Specifically, it’s going to be interesting to see how those people respond to jokes about the Biden administration doing some of the same stuff that Trump did. It’s easy to hate Trump because he’s hateable, but I’d be pretty surprised if Biden got all the kids out of cages or took down the border wall. Is that gonna be a tough pill to swallow for some of our audience? It’s not something I worry about when I’m writing jokes, but if it causes a big enough dip in our ratings, it will certainly come up in some fashion.

Our boss tells us, “We just want good jokes.” But if the good jokes aren’t pulling in the same kind of numbers as lukewarm jokes with a more palatable political take for our demo, strictly from a business perspective, that’s going to be something that someone, somewhere at the network has to think about. Fortunately, that person’s not me.

This story has been edited and condensed for clarity.

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What I Learned in the Late-Night Joke Mines