I asked AI to Create a New Yorker Cartoon for Me. It Didn't Go So Well.

Midjourney nailed the cartoon itself. ChatGPT's attempts at a caption failed utterly.

It seems like ChatGPT can do almost anything–write (bad) poetry, write (mediocre) English papers, take and pass an MBA exam. So why not get it to help me realize one of my childhood dreams: to get a cartoon into the New Yorker?

I grew up in a house overflowing with old copies of that august magazine. While as a kid, I wasn’t reading John McPhee’s 9000-word meditations on rock sediment, I always read the cartoons, and tried my best to draw my own New Yorker-style cartoons using pen and ink wash. Of course, I never sent any of them off to the New Yorker; even as a kid with big dreams, I knew they weren’t good enough.

But now I have artificial intelligence on my side. I began my quest by turning to the generative AI art program Midjourney, asking it to draw a New Yorker-style cartoon of a cat sitting at a desk in an office–a very New Yorkeresque cartoon premise, I felt.

Midjourney nailed it, popping out several cartoons, of which the one above was the most New-Yorkery.

I then asked it to draw me a variant on this cartoon with the cat at the desk talking to a kitten, perhaps offering advice. It nailed this one as well.

Now for the tricky bit–coming up with captions for the things. (Obviously, the captions that Midjourney came up with, however amusingly surreal they were, were not going to cut it.) This time I had ChatGPT to do the heavy lifting. I described the first cartoon to ChatGPT and asked for a list of captions.

Sadly, I have to say; I was a little underwhelmed. Here are some of them.

"I clawed my way to the top... of this desk."

"Another day, another dollar... or should I say, another mouse?"

"I may be feline the pressure, but I'm always purr-forming."

"I thought they said 'nine lives,' not 'nine to five.'"

I mean, there was an attempt. There were puns. ChatGPT realized that there could be humor in the idea of relating cat behaviors to the corporate life. It just failed to deliver any.

I asked for more.

"I may not be the CEO, but I am the Chief Executive Cat."

"I may be a cat, but I still have to work for the scratch."

“I refuse to use a scratching post, I have a perfectly good desk for that.”

There was one that really puzzled me.

"I told my boss I was a 'cat-titude' worker, not a 'cat-itude' worker."

I asked ChatGPT to explain:

Certainly! The caption "I told my boss I was a 'cat-titude' worker, not a 'cat-itude' worker" is a play on words that makes a joke about the cat's behavior in the office.

The word "attitude" refers to a person's behavior or demeanor, and it is often used to describe someone who is confident and assertive. By replacing the first letter of "attitude" with the word "cat," the caption creates the phrase "cat-titude," which is a pun that combines the word "cat" with "attitude." This suggests that the cat has a confident and assertive personality, and that it is a good worker.

So far this is what I expected.

However, the caption also includes the word "cat-itude," which is a play on the word "cat" and the word "altitude." This could be interpreted as the cat being high-handed or arrogant, suggesting that the cat may not be the best worker.

What. The fuck.

Overall, the caption is making a joke about the cat's personality and behavior in the office, and suggesting that it has a confident and assertive attitude, but may also have an arrogant or high-handed demeanor.

It’s worth reminding ourselves sometimes that ChatGPT, however human it might appear at times, is, in reality, a profoundly alien being that doesn’t think like we do or perhaps even think at all.

One funny caption?

The only remotely funny caption ChatGPT came up with was, I thought, this one:

"Just another day of pretending to understand spreadsheets."

What makes this funny to me, a little bit anyway, is that it makes no reference to the office worker being a cat. Just an ordinary schmoe at work pretending to understand spreadsheets, who happens to be a cat. That’s kind of funny. But is it New Yorker-level funny? Hardly.

So I went back to ChatGPT to get some captions for the second cartoon, where the office cat speaks to a kitten. The AI intuited that the older cat would be giving the younger cat advice about business, like some sort of cat mentor. Unfortunately, it didn’t make this advice funny.

"I may be getting older, but I still have a few tricks up my sleeve. And by tricks, I mean knocking things off the desk."

"I remember when I was your age, full of energy and curiosity. Now I just have a lot of paperwork and a coffee addiction."

"The key to success in the corporate world? Always land on your feet, and if that doesn't work, use your claws."

"Ah, the memories of chasing laser pointers and playing with string. But now, it's all about chasing deadlines and playing the corporate game."

It’s trying. And failing, but still trying.

"They say you can't teach an old cat new tricks, but I beg to differ. I learned how to use the printer all by myself."

Ok, that one was a tiny bit funny. Printers are so routinely dysfunctional they’re sort of inherently amusing. But not good enough for the New Yorker.

I’m not going to send either of these cartoons to the magazine.

But I haven’t given up yet. Maybe GPT-5 will have a sense of humor.

Note: I wrote this a little while back when ChaatGPT used GPT-3.5. I tried it again with GPT-4, but honestly, the jokes weren’t any funnier. A lot of them were worse.