Irony Illustrated: My Custom GPT for New Yorker Cartoons About the News
What happens when you feed headlines to a cartoonist with no hands and too much compute.
What Is Irony Illustrated?
I love New Yorker cartoons. The dry wit. The squiggly lines. The existential dread masked as charm. I don’t exactly seek them out on my own, but my wife and father-in-law have this wholesome tradition where she gifts him a New Yorker cartoon-a-day calendar every Christmas. He’s retired; she’s not. So naturally, he becomes the official curator—filtering through 365 panels of shruggy absurdism and sharing only the best.
It’s kind of like a personal Substack of middlebrow satire. Which got me thinking…
What if a GPT could generate that kind of cartoon—from just a headline?
Enter Irony Illustrated, a Custom GPT I made inside ChatGPT that transforms real news into imagined New Yorker-style cartoon prompts. Just drop in a headline and get back a perfectly absurd sketch idea—dry, ironic, and cartoonishly accurate in prompt form.
👉 Try it yourself here
How It Works
Paste in a real headline from CNN, NYT, ESPN, whatever.
It spits out a black-and-white cartoon prompt in New Yorker style.
You copy/paste the prompt into DALL·E, Meta AI, Grok or any Image Generator.
You marvel at the absurdity of our world.
Caveat: I’m only sharing the unique part of the prompt in this post. Every one of them includes boilerplate text like:
"A cartoon in the style of a New Yorker magazine sketch. Minimalist background. Black and white. Dry, intellectual tone."
Why These 6 Cartoons Made the Cut
I pulled 11 real headlines from CNN, NYT, and ESPN. Then I ran each through Irony Illustrated and generated images using three different models:
DALL·E (OpenAI)
Meta AI
Grok (Elon’s no-rules playground)
Then I picked the six funniest cartoons.
Confession time:
As an AI geek, I’m kinda embarrassed to admit this was my first time actually using Meta AI.
Yeah, I knew about it. It was super annoying when it first launched on Instagram. But I hadn’t touched it in a standalone setting until I was making the last image: a headline about Meta partnering with the UFC. I couldn’t not give Meta AI a try for that one. It just felt wrong.
Now here’s the real talk: not every result looked like a New Yorker cartoon. Some were way off stylistically. Some nailed the tone but failed the visuals. And nearly all of them had one tragic flaw: text.
Despite being called large language models, most of these tools are still totally useless at generating actual readable text in images. That’s the big irony here—language models that can’t write legibly. A lot of what they spit out was hilarious when paired with the caption, but made zero sense on its own. Like a punchline with no setup, or a sketch where the speech bubble just says “blorpt.”
Hopefully this improves soon with some much anticipated updates to DALL·E and other popular image generation models.
DALL·E probably came closest to actually matching the New Yorker style—but that didn’t always correlate with how funny or interesting the result was.
Anyways, here are the 6 funniest cartoons—with the winning model for each.
CNN – How to Make $3.8 Trillion Disappear in the Federal Budget
Prompt Snippet:
A magician on Capitol Hill labeled “OMB” pulls $3.8 trillion out of a giant top hat. The audience of taxpayers claps uncertainly. A child whispers, “Is this the trick where they forget where it went?”
Best Image: DALL·E
CNN – Trump’s Economic Team of Rivals Braces for Turbulence After Doing Little to Curb His Tariff Appetite
Prompt Snippet:
A chaotic airplane labeled “Trump 2025 Economy,” with Trump at the controls slamming the “Tariff” lever. Advisors wear parachutes and read “Free Markets for Dummies.”
Best Image: Meta AI
NYT – Trump Administration Delays Plan to Limit Pricey Bandages
Prompt Snippet:
Trump, dressed like a doctor, wraps a tiny paper cut in a $12,000 jewel-studded bandage inside the “Bandage Lobby HQ.” Aides wheel in platinum gauze.
Best Image: Meta AI
NYT – U.S. Bond Yields Spike as Tariff Turmoil Spooks Investors
Prompt Snippet:
Economists climb ropes attached to ballooning “U.S. Bond Yields.” A jack-in-the-box labeled “Tariff Policy” explodes with a Trump caricature in full war regalia tossing tariff confetti.
Best Image: Meta AI
ESPN – Lakers' Luka Doncic Wipes Away Tears, Then Whips Mavs in Return
Prompt Snippet:
Luka in a Shakespearean collar drops 40 on his old team while dabbing a tear with one hand. A scroll on his hip reads “Revenge, Act II.” Mark Cuban weeps in the wings.
Best Image: Grok
ESPN – UFC Partners With Meta to Expand Reach Through Technology
Prompt Snippet:
Fighters in VR headsets swing wildly in a UFC octagon. Zuck, wearing a ref shirt, gives a thumbs up next to holographic ads. A fan says, “I miss when punches landed in reality.”
Best Image: DALL·E
Try It Yourself
You can try Irony Illustrated right now:
Paste in a wild headline.
Copy the prompt it gives you.
Use that prompt in your favorite image model.
Witness modern absurdity, in cartoon form.
If your image model refuses (DALL·E is moody), try Meta. If that fails, summon the chaos engine that is Grok. I’m not responsible for what it draws—just what it was told.
Thanks for reading, and thanks in advance to the New Yorker cartoonist who’s already crafting the panel about a guy who made GPT write him a cartoon about making GPTs write cartoons.
We’re all just sketching in circles now.
—Charlie
PS - Between writing and posting this, I saw a headline so unhinged I had no choice but to make one more cartoon. I wasn’t about to rewrite this whole post, so here’s a bonus comic.
People – Surgeon Fined $10K After Sharing Photo of Swastika Tattoo on Coma Patient's Penis
Prompt Snippet:
In a sterile, fluorescent-lit hospital operating room, a group of surgeons stands over an unconscious patient. One surgeon, holding a smartphone mid-snap, turns to a colleague and says dryly, "I thought the Hippocratic Oath had a social media clause." The others look unimpressed, one jotting notes with a visible sigh. A whiteboard in the background reads “Today’s Procedure: Ethics Bypass.”
Best Image: DALL·E
Very clever. Ethics bypass bonus!