Irony Illustrated
News headlines in, dry New Yorker-style cartoon prompts out.
April 2025 (Updated Models in February 2026)
Custom GPTSatire
The Concept
The news is already absurd. Irony Illustrated takes real, published headlines — the ones that read like parody — and renders them as editorial cartoons using AI image generation. Each piece starts with an actual headline from a major outlet and ends up as something a political cartoonist might have drawn at 2am with unlimited coffee.
The project started as a question: can AI generate genuinely biting political satire? Not just "funny picture" — but a real cartoon with a point of view. The answer, mostly, is yes — with the right prompting strategy.
Tools Used
🤖
Converts any headline into a ready-to-use New Yorker cartoon image prompt
✦
GPT Image 1 / Meta AI / Grok
Image generation — GPT Image 1, Meta AI, and Grok all produce different styles
💬
ChatGPT 5.x
Powers the Custom GPT + caption writing
📰
Real news headlines
Source material — used verbatim
✂️
Substack
Publication + audience
The Gallery9 cartoons
Filter
The New York TimesAIFeatured Cartoon
How Was Trump's Speech? Choose Your Own Adventure
Two families watch the same speech on different screens. A robot with remotes stands between them. The algorithm decides what you see.
The New York Times
Feb 2026
CNNAIHow to Make $3.8 Trillion Disappear in the Federal Budget
A magician on a Capitol Hill stage, wearing a top hat labeled 'OMB,' waves a wand over a giant hat stuffed with dollar signs. The audience claps uncertainly.
CNN
Apr 2025
EconomyGPT Image 1
The New York TimesAITrump Administration Delays Plan to Limit Pricey Bandages
Trump as a doctor wrapping a paper cut in a jewel-studded bandage. Meta AI renders the absurdity in photorealistic detail.
The New York Times
Apr 2025
PoliticsMeta AI
The New York TimesAIU.S. Bond Yields Spike as Tariff Turmoil Spooks Investors
Economists climbing ropes as a tariff-themed jack-in-the-box explodes. 'Is this the invisible hand or just slapstick economics?'
The New York Times
Apr 2025
EconomyMeta AI
ESPNAILakers' Luka Doncic Wipes Away Tears, Then Whips Mavs in Return
Luka in a Shakespearean collar, dramatically scoring revenge on his former team. One tear rolls. The scoreboard does the talking.
ESPN
Apr 2025
SportsGrok
ESPNAIUFC Partners with Meta to Expand Reach Through Technology
Two fighters in VR headsets flail wildly in opposite directions. Zuckerberg referees. A fan in the stands laments: 'I miss when punches landed in reality.'
ESPN
Apr 2025
SportsGPT Image 1
The New York TimesAITrump to Undergo First Physical Since Retaking Office
A doctor holds a stethoscope to a golden statue. The X-ray shows 'approval ratings elevated.' The chart on the wall reads: 'Still no vital signs.'
The New York Times
Apr 2025
PoliticsGPT Image 1
CNNAITrump Is Waiting for Xi to Call. The Chinese See It Differently
A panda sits by a phone with a sign: 'We'll call when it suits us.' Across the table, the phone waits. Strategic patience meets strategic ego.
CNN
Apr 2025
PoliticsMeta AI
CNNAIUS Removes Commander in Greenland Following Vance's Controversial Visit
Inside an icy military outpost, a lone U.S. commander is escorted out while penguins watch. Diplomacy by subtraction.
CNN
Apr 2025
PoliticsMeta AI
Behind the Cartoons
How Each Cartoon Gets Made
Step 01
Find the headline
Scan major outlets for stories that are already unintentionally absurd. The best cartoons start from 100% real quotes.
📰 Real news
Step 02
Run it through the Custom GPT
Paste the headline into the Irony Illustrated Custom GPT. It outputs a complete, ready-to-use image generation prompt — New Yorker style, single panel, pen-and-ink, visual metaphor baked in.
🤖 Irony Illustrated Custom GPT
Step 03
Generate & refine
Feed the Custom GPT's output directly to GPT Image 1, Meta AI, or Grok. Usually takes 3–6 generations to nail the composition, perspective, and visual irony.
✦ GPT Image 1 / Meta AI / Grok
What Worked
AI Political Cartoon Learnings
| Technique | Result | Notes |
|---|---|---|
| Specify exact art style (New Yorker, broadsheet) | ✓ Works | Much cleaner than generic "editorial cartoon" |
| Include actual headline text verbatim | ✓ Works | Grounds the image; prevents GPT Image 1 from drifting |
| Ask for text / caption in the image | ⚠ Partial | GPT Image 1 renders text better than older models, but still inconsistent |
| Named real politicians or public figures | ✗ Blocked | GPT Image 1 refuses. Workaround: describe role/outfit/context without name |
| Metaphorical visual direction (show A doing B) | ✓ Works | Best results come from concrete scene descriptions, not abstract ideas |
| Multi-panel strip format | ⚠ Partial | Compositions often collapse — single panel is more reliable |
Read the Full Story
Irony Illustrated: My Custom GPT for New Yorker Cartoons About the News
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