You know the feeling. You’re sitting in a waiting room, or maybe at a coffee shop, and you pick up the magazine. You flip to the back, or maybe you're just hunting through the ads. You see a drawing of two cows wearing business suits. One is holding a briefcase. The caption says something about "synergy" or "the grass being greener on the other side of the merger."
You smile. Or you stare at it for thirty seconds trying to figure out if you're dumb or if the joke is just that high-brow. That is the magic of New Yorker cartoons. They’ve been a staple of American culture since 1925, and honestly, they haven't changed that much, which is probably why they still work.
The Art of the "Huh?" Factor
Most people think a cartoon's job is to make you laugh out loud. But that’s not really what Bob Mankoff, the longtime cartoon editor, was going for during his tenure. He often talked about the "humor of recognition." It’s that little spike in your brain when you realize the drawing is mocking the exact kind of person you saw at Whole Foods ten minutes ago.
It’s sophisticated. It’s dry. Sometimes it’s just weird.
Take the famous "On the Internet, nobody knows you're a dog" cartoon by Peter Steiner from 1993. At the time, it was just a funny commentary on the anonymity of the early web. Now? It’s arguably the most reproduced cartoon in the magazine’s history. It’s been on mugs, t-shirts, and probably a few million PowerPoint slides. It works because it captures a universal truth before we even realize it’s a truth.
Sentence length doesn't matter when the vibe is right. Some of the best ones have no caption at all.
How the Sausage Gets Made
Every week, hundreds of professional cartoonists—and thousands of hopeful amateurs—submit their work. They call it "the look." Cartoonists like Roz Chast or Emily Flake bring in a batch of rough sketches. The editor looks through them. Most get rejected. In fact, most great ones get rejected.
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The selection process is brutal. It’s not just about what’s funny; it’s about what fits the "voice" of the magazine. That voice is often described as "urbane," which is really just a fancy way of saying it’s for people who live in cities and worry about their therapists' opinions of them.
Why New Yorker Cartoons Break the Internet (Every Week)
You've probably seen the "Caption Contest" on the back page. It started in 2005 and basically turned the entire readership into unpaid comedy writers. It’s genius marketing. It forces you to engage with the art.
But there’s a deeper reason these single-panel drawings thrive in the age of TikTok and 10-second reels. They are the original memes. Long before we had "Distracted Boyfriend," we had New Yorker cartoons. They are a single image that tells a whole story. They’re fast. You can consume one in three seconds, but you might think about it for three minutes.
People like David Sipress or Liana Finck have mastered this. Finck, specifically, uses a very "unrefined" style that looks like it was doodled on a napkin. It feels raw. It feels human. In a world of AI-generated art that looks too perfect, there’s something deeply comforting about a shaky pen line and a joke about social anxiety.
The Evolution of the "Vibe"
If you go back and look at the cartoons from the 1940s, they’re different. They’re wordier. The art is more lush. Charles Addams (yes, the Addams Family guy) was a regular. His stuff was dark. It was macabre. It pushed the boundaries of what a "funny" drawing could be.
Then came the 60s and 70s. The jokes got more psychological.
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Now? We’re in a weird, meta-era.
Some cartoons today are just about the absurdity of being alive in 2026. They tackle climate change, zoom calls, and the soul-crushing reality of the gig economy. But they do it with a wink. It’s not a lecture; it’s a commiseration.
The Cartoon Bank and the Business of Wit
It's not just a hobby. It's a business. The Conde Nast "Cartoon Bank" is a massive archive where you can buy prints or licenses for these drawings. If you want a cartoon for your textbook or your corporate retreat, you pay for it.
This brings up an interesting point about E-E-A-T (Experience, Expertise, Authoritativeness, and Trustworthiness). The magazine has maintained its authority because it doesn't chase trends. It is the trend. When a cartoonist gets published in the New Yorker, it’s like a musician playing Carnegie Hall. It’s the gold standard.
But it's not perfect. For decades, the roster of cartoonists was... let's be honest, it was mostly white guys in New York. Under current editor Emma Allen, that’s finally shifting. There are more women, more people of color, and more diverse perspectives than ever before. This hasn't "ruined" the cartoons; it’s made them sharper. The humor is less about "my wife is annoying" and more about the actual complexities of modern life.
How to Actually "Get" a New Yorker Cartoon
If you’re looking at a cartoon and you don’t get it, don't panic. Here is the secret:
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Sometimes, there is no joke.
Sometimes the "joke" is just the absurdity of the situation. Or the joke is a reference to a specific literary trope or a piece of news you might have missed.
Pro Tip: If you're really stuck, try replacing the caption with "Christ, what an asshole." It’s an old internet theory that this caption works for about 90% of New Yorker cartoons. It’s surprisingly accurate.
But seriously, the best way to appreciate them is to stop trying so hard. Look at the expression on the characters' faces. Usually, the humor is in the gap between what the character is saying and how they actually look.
Actionable Steps for Cartoon Enthusiasts
If you want to dive deeper into this world, don't just scroll past them on Instagram.
- Follow individual artists: Check out Liana Finck, Will McPhail, or Emily Flake on social media. You get to see their "rejected" piles, which are often funnier than the ones that make it in.
- Study the composition: Notice how the artist leads your eye. There’s usually a "hero" of the drawing and a secondary detail that provides the punchline.
- Try the Caption Contest: But don't be basic. Avoid puns. The winners are usually the ones that are a bit "off-center" or slightly melancholy.
- Visit the Archives: If you have a subscription, use the digital tools to look at cartoons from the 1930s. It’s a fascinating time capsule of what people used to find stressful (mostly hats and servants).
The New Yorker cartoon isn't just a drawing; it’s a mirror. It shows us our vanities, our fears, and our ridiculousness. As long as humans are weird and socially awkward, these cartoons will stay relevant. Go grab an issue, find a weird drawing of a cat in a therapist's office, and just let yourself not get it for a second. That’s part of the fun.