It’s an article of faith in literary circles that the proper way to read the New Yorker is to start with the cartoons and then place the magazine atop a neat pile of older issues and wait for nuclear winter to free up time to read the rest. Ever since the New Yorker’s first issue hit newsstands in 1925, these cartoons—cosmopolitan, sly, absurdist, and sometimes obscure—have been a treasured part of America’s visual culture, knitting together aspirational sophisticates across the country by letting them in on a multifarious common joke and a shared style of laughing at the world, through good times and bad. Over the past near-century, great cartoonists left their mark on the magazine’s pages and moved on—but very little about the cartoons themselves changed.

Now, since May, these cartoons are in the nimble hands of a new cartoon editor, the 29-year-old humor wunderkind Emma Allen. And the times they are a-changin’.

A journalist who got her professional start at Artinfo, where she worked alongside several current artnet News editors and evinced an arrestingly funny style covering everything from Katy Perry’s album designs to Bravo’s “Work of Art” reality show, Allen moved over to the New Yorker five and a half years ago and clambered up the masthead, first taking over the written humor sections and now the cartoons. A key to her success at the magazine has been her digital savvy, and, since she began, the New Yorker’s online humor has become a big part of its business. Now she is poised to continue this web migration with the cartoons, with wide-reaching implications for their many fans. Soon, we may be able to indulge in the New Yorker’s cartoons before we read anything whatsoever.

But don’t worry—Allen, in many ways, is a traditionalist. To find out more about where the magazine’s cartoons are headed, artnet News editor-in-chief Andrew Goldstein sat down with his old colleague to find out what their possibilities are online, who the next generation of great cartoonists will be, and how they can get her attention.

We’ve known each other for a long time, so when you segued from art journalism to humor for the New Yorker, I wasn’t too surprised—because you’re probably the funniest person I’ve ever met. And it’s not just because you have a unique, whip-fast sense of humor. It’s also because the world seems to throw funny things at you. You can walk down the street and something hilarious will happen to you. Many times, these are accidents; on certain occasions, they are not not embarrassing. When you relate what happened, people laugh. What’s your secret?

My nickname in college was the Queen of Catastrophe, because even my most well-meaning outings always ended in disaster. Which was sometimes funny. And the curse hasn’t abated!

You’ve always included observational humor in your writing, but when you were growing up did you ever think of pursuing humor professionally?

No. In college I did at one point have a column in the paper called “The Unethicist,” which was meant to be an advice column where I gave out the worst possible advice. That’s the closest I’d ever come to doing intentionally humorous writing. But that comedic drive has been the through-line in all of my various jobs, because I tend to observe the world by, as we say in the Talk of the Town department, “watching people hang themselves.” Rather than generating my own comedic fodder, I like to keep an eye out for what is funny in what’s going on around me.

I’m drawn to the classic Lillian Ross mode of writing, and even E.B. White—this sort of dry, observational style. What you get ends up being funny without actually having to write your own jokes. That’s why I hated having to do improv for that piece I wrote about the Upright Citizens Brigade! Having to be the funny guy on the stage is not something I derive pleasure from.

So you’re like the Henri Cartier-Bresson of humor, on the lookout for the “decisive moment.” 

No, it’s true! I did study photography—I double-majored in studio art and English—and what I’ve always liked about photography is that everybody has the same materials available to them. It’s very democratic, an easily reproducible and relatively cheap art form. But what you’re really doing is framing—it’s the crop that makes something good or bad. As my senior thesis, I ended up doing these really weird-ass collages, where I took family photographs, Polaroids, and crappy photos I’d taken of my friends and then bought all these really obscure books, manuals, and catalogs of dolls, and collaged them all together to create odd personal vignettes.

In a way, that sounds like a good mix of skills for someone who is an editor of cartoons.

Yes. It was so obvious, as soon as I graduated with my double major in English and Fine Art, that I would become cartoon editor.

There are lots of editors in the world, but very few cartoon editors. In fact, is there anyone else you can think of who has a similar cartoon-editor job?

I guess there are people who run websites that publish comics, and there are certainly people at Drawn and Quarterly. There are also some British ones like Punch and Private Eye, which are all really insider-y parliamentary jokes that I don’t understand. But the thing is, the cartoon in the New Yorker sense doesn’t really exist any other place in the world. We’re pretty much the only game in town.

You joined the New Yorker a few years ago as an editorial assistant. Can you describe the winding career path that took you to your new role?

I started as the assistant to Susan Morrison, who edits Shouts and Murmurs and Talk of the Town and is currently writing a book about [“Saturday Night Live” creator] Lorne Michaels. Basically, she’s the great onetime Spy magazine editor who totally transformed Shouts. So I was working with her doing a lot of assistant stuff, trying to exorcise the ghosts that were constantly in her computer, making photocopies—badly—and opening mail. I also slowly started to do line edits on Shouts and Talk, which is a fun section—it’s like a puzzle that you have to put together every week. One of my jobs was to pick the little [Otto] Soglow spots that go at the top of all the different items.

You’re referring, of course, to those classic little cartoon drawings that go at the top of each item in the Talk of the Town section. They’ve been in the magazine every week for decades, but what most people don’t know is that the artist actually died in 1975. How does that work?

Otto Soglow drew them specifically to accompany different articles over many decades, and we have huge binders of them organized by category. I would go through and cherry-pick ones that I thought were sort of funny to go with items in the Talk section, because the drawings are just evergreen. Most of them at least—there are also a lot of them that are super racist, some crazy KKK ones, and Hitler ones.

Like pro-Nazi?

No, more like Hitler reading the New Yorker in a bombed-out building… we’ve spent a lot of time trying to reverse-engineer what article could’ve possibly generated the spot. For a while, we switched over to having someone draw new versions for the articles, but they weren’t as witty or good—it was just an illustration of the story versus a sort of visual slant rhyme. Talk is already so slant in its approach, so it was a better fit. Soglow was a genius. He was a cartoonist here too. I have a Soglow that Susan made into a magnet for me. Everyone from the Talk department got them as a Christmas present, with each of us getting a spot that represented us in some way, and mine is of a naked woman holding a hammer and a sickle and dancing in heels.

She must have liked you. What about Tom Bachtell, the artist who draws the illustrations that appear in the Talk items themselves, depicting what they’re about? Did you work with him too?

Yeah. I don’t know him that well personally, except that I corresponded with him over many years, saying things like, “Can you draw Cate Blanchett while she’s holding a…” fill in the blank?

He pretty much operates on his own. But I did get to send lots of fun emails being like, “We want these Palm Beach poodles, except they’re climbing over a bed, and there’s a dog underneath them, and Trump is behind the car!”

So you were essentially cartoon-editing from the very beginning. When did you start to get more involved with Shouts and Murmurs, the magazine’s famous humor column?

Around the time I joined the magazine we decided to launch Daily Shouts, which would be an online vertical platform for more frequent humor, and we brought on Andy Borowitz to do his thing on the site. At first it was just a dumping ground for rejected Shouts, but then, about three or four years ago, I started working on it more. I didn’t really have an agenda, except that I was spending a lot of time going to comedy shows, and a lot of my friends were writing for late night and other TV shows, so I started to recruit people to write Daily Shouts to give it a more intentional and responsive feel. Slowly I just became the point person for all of the humor that was coming in, and then I officially became the editor of the section. That became a big part of my job, but I was also still working at Talk and Shouts, now as an assistant editor, and writing Talks, and writing a couple of longer pieces, too.

But the Daily Shouts site was something you kind of carved out for yourself.

Yeah—with no plan to do so. But it ultimately became the thing I liked doing the most. I also was—and to a certain extent still am—reading everything in the slush pile, which when I started was a real disaster zone because people didn’t really know what Shouts and Murmurs were. Some people would, you know, send in these long depressing essays about how their brother died of leukemia, and they’d be like, “This is more of a murmur than a shout,” and you’d be like, “It’s really neither in this context.”

But, over time, as Daily Shouts became more of a thing, the slush pile actually became really good. We started getting a lot of people through the slush pile, and ultimately it became a great resource.

You’ve built the online humor section into a incredible success, with millions of readers and talented contributors who go on to bigger and better things. Just how successful is it?

Well, I had the benefit of having stumbled upon this thing I love doing, and having a good network of people to help me with it. Also, it’s almost cheating, because humor on the Internet is, like, whoa. But I won some Condé corporate award that came with a Tiffany paperweight calling me a Q4 Accelerator for generating 20 million page views. I remember it was 20 million, because I called my best friend, Susanna [Wolff], who was the editor in chief of College Humor then and now writes for the new Bobby Moynihan show, and she said, “Yeah, I just posted one picture of boobs with a funny caption on College Humor and it got like seven times that.” So in the context of quiet, deeply reported magazine journalism on the web, humor stuff does really well. But not compared to pictures of boobs on College Humor.

You could always bring pictures of boobs into the New Yorker.

That’s true, like between every other paragraph. They’d have to be very small.

What about the Borowitz Report? It’s gigantically popular, though for a while it was kind of confusing because it wasn’t clearly marked as humor, and its headlines—like “Millions Willing to Work for Mueller for Free If That Would Speed Things Up”—edge into the realm of plausibility. Recently, that changed, and now it has disclaimers saying it’s satire and “not the news” all over the place.

People wanted to rebrand the Borowitz Report after Trump was elected, to make it clear that it wasn’t fake news—to mark it. But that generates a huge following. Going by the number of clicks, I think it gets more readers than anything else on the site. I once gave an impassioned, Mr. Smith Goes to Washington speech side by side with him about how satire wasn’t fake news. We’re basically just buddies.

What’s amazing is that the New Yorker was founded in 1925 as a humor magazine, and now it actually seems to be becoming a humor magazine for the first time.

Yeah! Among other things. There are some deadly serious, very unfunny clicks on the site too, if you’re not careful.

What is the balance of the humor section with the serious news division, in terms of the volume of content?

In terms of what we’re publishing online, I’d say 12 to 15 things go up a day, generally, and three or four of those are funny things. So it’s a pretty large percentage of what’s going up. Sometimes, it’s like, “Yeah, I posted a daily cartoon,” so that’s one post. And then some poor schmuck had to go to Russia for four months to report out an incredible investigation, and that’s another post.

Your predecessor, Bob Mankoff, is a cartoonist who was hired 20 years ago by Tina Brown, in a very different publishing era. When he retired, you—a young, web-savvy non-cartoonist—were a surprise choice.

It certainly surprised the cartoonists.

How did that happen?

Well, David talked to me about creating a role that was editing humor more broadly, and which would take in cartoons. I think the cartoonists are pretty happy with the new arrangement because there are a thousand cartoon submissions every week and only about 15 things are bought. So it used to be that even our most beloved, most frequently published cartoonists were producing a ton of work but not necessarily making money every week. Now they are also doing daily longer comic posts for the web, writing shouts, and illustrating shouts for me; some of them are working on video, too. So there are many more ways to be published and make money, and also to get feedback from an editor who you’re dealing with all the time versus throwing cartoons into the ether and desperately awaiting okays.

What was the transition like? How were you introduced to the cartoonists?

The cartoonists got an email announcing the changing of the guard, and then Bob had a sort of farewell tour with people coming to say goodbye. On his last day, there were hundreds of cartoonists coming in. I had been making all of these flash cards, because I knew all of these cartoonists by their signature and cartoons, but who on Earth knows what any of these people look like!

That sounds like a challenge.

Yes, although many of them do look like the people in their cartoons, so there was a little bit of a tipoff. But, anyway, for the first couple weeks people basically came into the office wanting to get a sense of who the hell I was, whether I was going to be incredibly mean and throw them overboard, or whether I had this grand vision that was going to totally change everything. By now I think everyone knows I’m not intimidating at all, but those first couple weeks were mostly cartoonist meetings where people came in and sat there, and I quaked and they quaked, and I sweated and they sweated.

An editor typically has to know the rules of style and grammar better than the writers. Does a cartoon editor need to understand the rules of funny better than the cartoonists?

I actually have an aversion to any idea of the rules of funny, because if I’ve learned anything from editing Shouts over the past five and a half years, it’s that the things that are the funniest defy the rules. And that’s especially true at the New Yorker, where people try to create something that they think feels like a “New Yorker Shout piece” or a “New Yorker cartoon,” and it comes off as canned version of a bad imitation. I always find it’s much better when something feels totally unlike a thing you’d expect to find in the New Yorker and still makes you laugh every time you encounter it.

The magazine’s fiction editor, Deborah Treisman, once said that there was no set template for a New Yorker story, just that whatever the story sets out to do—to be a linguistically ingenious postmodern story, or an emotionally gripping narrative—needs to “succeed on its own terms.” It sounds like you’re saying something similar for the cartoons. 

Also, so much of humor is inherently surprise, so as soon as you get into anything that’s too formulaic it ruins the joke. And you only have so many chances in a cartoon. You have one second of processing the image and one second of processing the line, and if there’s no surprise anywhere in that it’s probably not that funny or good.

I think one anxiety that a lot of the cartoonists had is that I wouldn’t know anything about art, or the drawing side of things, because there is a real level of expertise there, and specialized craft. There have only been three people who did this job before me and two of them were cartoonists, so there was this sense of, “Oh no, how can a non-cartoonist do this thing?” But, you know, I know a little bit about art.

It’s also striking that, as a millennial, you’re leading this gaggle of cartoonists that includes some nonagenarians who have been at the magazine forever. For instance, George Booth, the legendary Missouri-born cartoonist of shotgun shacks and neurotic pets, is now 91 years old and still contributes regularly. What’s it like working with him?

He comes in almost every week. He recently sent in a cartoon that won’t end up in the magazine but just made me laugh so hard. It involved these old women on a porch, in this classic George Booth setting, while a guy is working in the yard, and the caption was, “Laverne”—or whatever his George Boothian name was—“is no good at composting, but gee whiz you should see him in bed.” Just a really raunchy composting joke that just killed me.

So what happened to it?

I think David [Remnick] blushed and politely declined.

That raises the question: do you have to run all the cartoons by David Remnick before they can be published? What is the process?

Yes. So it goes like this: I get a thousand submissions, and then Colin Stokes, the associate cartoon editor, and I go through them together in a daze and winnow them down to around a hundred. Then I look at them again and get it down to about 60, and then, from there, David buys between 15 and 20.

So he’s the ultimate decider.

Yeah. We have these meetings where I feel very huckster-ish, where he picks up a cartoon out of the pile and I go into pitch mode, like, [high-pitched, sped-up voice] “Well, the interesting thing about this, you know, is the person who drew that has a funny story, see….” Or, “You know, the one with the cat is not really about a cat, it’s about….”

You’re like the Don Draper of funny doodles.

But I’m like Don Draper on speed, because I only have like five seconds before David decides to move on.

Because he’s got Netanyahu and Bob Dylan in the next room, waiting. 

Yeah, exactly.

To go back to your cartoonists, as one might expect, many of them are quirky, interesting people, some of whom have quirky, interesting side jobs. Alex Gregory, for instance, is also a Hollywood screenwriter who has written for “Veep,” “Frasier,” and once directed a film called A Good Old Fashioned Orgy. Is cartooning something that most of your contributors do in addition to something else?

Well, there is definitely a generational difference. With the older guard, for many years they made a living from cartooning, because the New Yorker wasn’t the only game in town. On Tuesdays they would go from publication to publication, starting with the Saturday Evening Post, because they had jelly donuts and they paid the most, and then to Playboy, the New Yorker, and Colliers. By the end of the day, they’d have sold their entire batch to one place or another. Now that’s not really possible anymore.

What are some other interesting side jobs?

Kendra Allenby works at a tech startup where she draws out esoteric technological concepts in these cartoon-like processes to explain them to visual thinkers, so that they make sense. Bruce Eric Kaplan is also a TV writer.

Kaplan, it so happens, is the guy who wrote the famous “Seinfeld” episode “The Cartoon,” where Elaine confronts the New Yorker cartoon editor over a nonsensical cartoon—only to find out he doesn’t get it either and just “liked the kitty.” Tell me the truth: do you always “get” the cartoons you publish?

That’s one of the many values of looking at them with Colin. We’ll come to a cartoon and he’ll say, “Oh, that’s hilarious,” and I’m like, “Wait… why?” Or sometimes we’ll both think something is so funny, and then when we show it to David and he doesn’t get it we’ll realize that we both had totally different interpretations of it.

There was one a little while ago with people in bed doing a crossword puzzle, looking for a word with six letters, and that’s the whole cartoon. I thought the word was was “orgasm,” and Colin had thought it was something totally different, and David thought it was something totally different, and then we all just sat there like, “Let’s all just never talk about this again.” It was just the most horrifying conversation where I’m saying the word “orgasm” to my boss, and also we were all probably wrong.

Did you ever check?

No.

Cartoons are a format that has been around for centuries, going back to Daumier and further to the naughty captioned murals in Pompeii.

Yeah. Cave paintings used to have captions, they just wore off faster.

At the same time, they are almost cutting-edge, in a way, because they are ideally suited to the kind of instant visual communication we have on social media. How do cartoons fare online?

Before I started as the editor, a wonderful woman at the New Yorker named Lainna Fader decided to create a cartoon Instagram account, and it blew up, obviously. Because cartoons have this weird alchemical combination of pleasing drawings and jokes—they’re like the ur meme. Before anybody was writing “cheezburger” on cats, we were doing that. We have all of the cat cartoons of all time, so this is something that sort of does the work for itself online.

With the Daily Cartoon, though, we totally reworked how it gets published. It used to be that a cartoonist would just get tapped for however many weeks and they would just send something every day to get a light copyedit and go up. Some of them have an incredible stamina for doing this, but sometimes people were burning out and we would get things that weren’t very good but that we’d have to publish because it was all we had.

So after I took over, Colin and I modeled the process on the Onion headline-submission process, where every morning they send a bunch of ideas and we pick one right when we wake up. In the Trump era this has been great, because cartoons in the New Yorker are not usually explicitly political—though they can often be political in a wry, arched-eyebrow way, like using the recurring “king” conceit as a way to talk about Trump. Now, with this Daily Cartoon, we’re responding to the latest breaking news. And, sometimes, even in the hour it takes us to post it, it already feels tired. But it’s a fun way to use cartoons with a timeliness that you can’t have in a weekly magazine.

There seems to much more latitude in what you publish online too, even in terms of format. Not everything is a single drawing with a single caption.

Yeah, we’re also doing these Daily Comics as a way to get in a much broader base of contributors who don’t necessarily work in the gag format and aren’t necessarily interested in doing single-panel stuff, but are the great artists and writers in this new, incredibly vibrant world of graphic novels and web comics and ‘zines.

It’s not like in the magazine where there is a word count, and specific topics that we’re looking for. So sometimes we have these weird lyrical drawings, sometimes it’s a classic multipanel comic strip, or we are excerpting graphic novels.

You mentioned Trump, and it reminds me that Seth Meyers recently said that Trump “thinks in cartoons.” Well, evidently cartoons also think in Trump. For two months this summer, every daily cartoon has been about Trump or politics except for three—one about firework-singed birds wishing each other a “happy Fifth of July,” one about Penn Station being the pits of hell, and one about Travis Kalanick hailing a taxi after getting fired from Uber. Do you ever worry that the continual satirical focus on Trump will turn some people off?

That we’re going to alienate Trump supporters? I think if the election taught us anything, it’s that everyone is siloed in their own media consumption already, and the New Yorker already feels pretty strongly that it has a responsibility to take on Trump as he dismantles our democracy in any way that we can. Satire is a really good way to do that, and he definitely presents himself as a prime target for it by acting like an idiot all the time. I think the bigger concern for me is finding the right balance, because I think satire stops functioning when you’ve become weary of it—you just glaze over. It goes back to the importance of surprise. Also, humor is very pleasant as an escapist form, so it’s nice to occasionally be able to stop thinking about Trump and instead think about how stupid La Croix water is as a fad.

So, in a relatively short span of time, you’ve taken the New Yorker’s humor and cartoons to a whole new level of visibility, with the online components, the sensational Cartoon Lounge video series, the podcasts. As you’re tackling this venerable part of the magazine, what are some other directions you could take it? Will there ever be a “Lego Movie” for George Booth’s dogs?

I would watch that forever. Actually, David told me, “Remember how National Lampoon was a magazine and then a Hollywood presence that created its own feature-length films? We should do that.” And I’d love to do that, but currently my days are spent just getting all of the stuff up, and fielding the never-ending content submissions. I would love to do more animated stuff, too, although in some ways the great thing about the gag cartoon is its purity. It’s the art of distillation, conveying a complex joke in a compact format, sometimes without even a caption. Building that into a VR thing with cartoons? In some ways it could be cool, and I’m sure we could do something that is narratively interesting and get great comedy writers on it, but part of the joy of the cartoon is its format exactly as it is. So as much as I have grand plans to do longer comic stuff, and videos, and definitely animated videos online with the cartoonists, I’m also as beholden to preserving this gag style in some version of what it is.

Like ancient Greek lyric poetry, or the haiku. Do you get a lot of letters from readers defending the house style and decorum?

I get a filtered selection, thankfully. Some real good ones come through, though. My favorite one for Shouts came after a really great Canadian writer named Scaachi Koul wrote a piece that was a very gentle mocking of dads, about a dad restaurant where everything in the place catered to dads. It was very soft and sweet, and this woman wrote in and was enraged. She said, “I can’t believe you published this—it’s so insensitive. Aging is a real problem, especially for older Americans.”

Your predecessor started in this job 20 years ago as a lowly cartoonist and left a fabulously wealthy cartoon tycoon—or, as you might call it, a tycoonist.

I saw that one coming.

Now leads this fancy life and drives a Tesla. How did that happen?

Well, he sold Tina Brown the Cartoon Bank concept, where anyone can license New Yorker cartoons for their own purposes. It’s now owned by Condé Nast. He is also a very compelling public personality, in a way that I fear I will never live up to. He sold a lot of cartoons, he sold a lot of books, and edited a lot of books. And then he got a Tesla.

There’s even a Cartoon Lounge video of him driving around in his Tesla, which I believe was on autopilot. 

And then I did mine on my skateboard, which is my Tesla.

I didn’t realize Tesla made skateboards.

No, my skateboard is from high school, and it has a Yale sticker on it, and a Triple A sticker. I dusted it off for the Cartoon Lounge.

As the young editor coming in, part of your job is to cultivate a new generation of talent. After all, as you mentioned, aging is a real problem among older Americans. How do you go about finding new talent cartoon to bring in?

It’s an interesting dilemma, because while there are a lot of very funny people out there, they aren’t really making gag cartoons on their own, except for the real fanboys and girls out there, who tend to be pretty insane. So it requires approaching people who are in this vibrant other world of graphic novels and comic arts and first, figuring out if they are interested in trying their hand at this very specific, weird thing—which many of them aren’t—and, second, deciding if it’s worth trying to convince people to do this thing that feels unnatural to them.

One thing we might do is start pairing up gag writers and artists, which was a big part of the history of the New Yorker. I have no specific aversion to that. There’s also just a lot of trolling the internet. Instagram has been incredibly useful, because people who work in comic forms tend to be on Instagram. And when you start to follow them all compulsively, the platform will start suggesting people for you to follow—because the world of graphic arts and comics is vaster than the current pool of people who contribute to the New Yorker, but it’s still an insular world. Everyone knows each other, and they all go to the same conventions.

I had a very brief stint working in the New Yorker’s library once, and I actually tried to draw a cartoon. It was a old-fashioned, curly-haired woman sitting at a desk in front of an office, and she’s reaching for a ringing telephone when, at the same time, an identically permed woman leaps athletically out from the right, grabbing the receiver first. The caption was “Interceptionist.” 

I could’ve guessed you would have had a really punny cartoon.

I gave the cartoon to an assistant, who brought it to the cartoon editor, Bob Mankoff, and I think I was escorted out of the building. Do you have any advice for aspiring cartoonists?

Well, they can get in touch with me. They can come in on Tuesdays between 11 am and 1:30 pm. I have all sorts of crazy people come in, so if you are relatively non-crazy and have a good cartoon, I will be pleased to see you.

Do you have donuts?

The first month I brought in donuts for the cartoonists, and I had fresh flowers on my desk every week, to bring the feminine touch that I’m known for to the office. Eventually the will to sleep in overcame both my generosity and my interest in the feminine touch, so I stopped.

You’re becoming a pro. Any other advice?

I do not love a punny cartoon, ahem. It helps, like anything, if you study the form, but then keep in mind that you’re not trying to imitate anyone else’s style or voice. It’s the breadth of new voices and perspectives and new types of jokes that makes it better. It’s also worth knowing that I came up on the classic ‘90s sitcoms, and I do love Jerry Seinfeld, the cutting observational joke that feels very specific. Recently I got a submission that I loved of a croissant lying in the desert, with the caption, “The driest croissant in the world.” But it has to feel specific and real, not just broadly stated stereotypes about whatever world people think New Yorker editors live in, because it ain’t me! I don’t drive a Tesla.