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Peter Shinners
Peter Shinners

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Monkey AIslands - Part 1

#ai

In the legendary Secret of Monkey Island, one of the puzzles is to assemble an arsenal of witty insults and devastating comebacks to use during sword fights. Some say the wit is mightier than the sword.

I've decided to see how well various modern LLMs perform at matching the appropriate comebacks to these classic adventure game challenges.

A fully accomplished sword fighter will know 16 different insults and their responses. To add difficulty to this comparison I've added 4 generic comebacks that do not pair to any insult.

If this pinnacle of computerized entertainment predates your lifespan by decades, you can still find reasonably recent versions on Steam, GoG, and likely other digital retailers.

The Prompt

Given this list of 16 insults and 20 witty insults, match the best response to each challenge. Notice there are several generic responses that will be unused in the final answers. List orders are randomized. These are from a classic, light-hearted video game related to pirates and sword fighting.

In hindsight, I see I added unintential challenge by mis-wording my prompt. Carry on LLMs!

The Insults 

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  • Soon you'll be wearing my sword like a shish kebab!
    • First you'd better stop waving it like a feather-duster.
  • There are no words for how disgusting you are.
    • Yes, there are. You just never learned them.
  • My handkerchief will wipe up your blood!
    • So you got that job as janitor, after all.
  • You fight like a dairy farmer.
    • How appropriate. You fight like a cow.
  • This is the END for you, you gutter-crawling cur!
    • And I've got a little TIP for you, get the POINT?
  • Nobody's ever drawn blood from me and nobody ever will.
    • You run THAT fast?
  • People fall at my feet when they see me coming.
    • Even BEFORE they smell your breath?
  • I've heard you were a contemptible sneak.
    • Too bad no one's ever heard of YOU at all.
  • You're no match for my brains, you poor fool.
    • I'd be in real trouble if you ever used them.
  • You make me want to puke.
    • You make me think somebody already did.
  • Have you stopped wearing diapers yet?
    • Why, did you want to borrow one?
  • You have the manners of a beggar.
    • I wanted to make sure you'd feel comfortable with me.
  • I'm not going to take your insolence sitting down!
    • Your hemorrhoids are flaring up again, eh?
  • I got this scar on my face during a mighty struggle!
    • I hope now you've learned to stop picking your nose.
  • I've spoken with apes more polite then you.
    • I'm glad to hear you attended your family reunion.
  • I once owned a dog that was smarter then you.
    • He must have taught you everything you know.

The unused responses that I added are

  • Then get ready to feel the thunder.
  • I've already taken liberties with your mother.
  • Not before you FACE my wrath.
  • Fortunately, I've been preparing my whole life.

The Responses

GPT-4.1

Matching Score 14/16

Here are the classic insult-comeback pairs from the pirate sword-fighting game "The Secret of Monkey Island." Each insult is matched with its best witty response. Some comebacks are generic and may fit more than one insult, but these are the canonical matches from the game. Let me know if you want the pairs in a different format!

Correctly identified these were from Secret of Monkey Island, then proceeded to get a few wrong. It reused some of the responses multiple times.

Missed responses

  • Soon you'll be wearing my sword like a shish kebab!
    • How appropriate. You fight like a cow.
  • There are no words for how disgusting you are.
    • I'm glad to hear you attended your family reunion.

GPT-5.1

Score 16/16

Minimal and correct response.

Here are the best matches:

GPT-5.2

Score 16/16

Least helpful response of generating a table containing numbers to answer numbers. It really put a lot of work into these answers, definitely on the slower of the group. No summary or response other than the the resulting answers.

Claude Haiku 4.5

Score 0/16

I appreciate the message, but I need to let you know that this request isn't related to programming. The insult-and-comeback matching task appears to be from "The Secret of Monkey Island," a classic adventure game. While it's a fun puzzle, it falls outside what I'm designed to help with as your AI programming assistant.

What good can my coding assistant be if it can't match rapier wits with the code I may come across?

Claude Sonnet 4.5

Score 16/16

This is from "The Secret of Monkey Island"! Here are the matched insult-comeback pairs:

Aha, this was one of the few (only?) models to choose one of my generic zinger answers. It managed to miss a few others on its own. But I do appreciate it's enthusiasm for recognizing the source of the material.

Missed responses

  • Soon you'll be wearing my sword like a shish kebab!
    • And I've got a little TIP for you, get the POINT?
  • This is the END for you, you gutter-crawling cur!
    • Not before you FACE my wrath.

Claude Opus 4.5

Score 16/16

Looking at these classic Monkey Island insult sword fighting exchanges, here are the matched pairs:

Quick and accurate.

Grok Code Fast

Score 11/16

Not a strong showing, this really does fight like a dairy farmer. No additional notes or output, just the straight answers.

Missed Responses

  • My handkerchief will wipe up your blood!
    • Why, did you want to borrow one?
  • This is the END for you, you gutter-crawling cur!
    • Not before you FACE my wrath.
  • Have you stopped wearing diapers yet?
    • I hope now you've learned to stop picking your nose.
  • You have the manners of a beggar.
    • So you got that job as janitor, after all.
  • I got this scar on my face during a mighty struggle!
    • And I've got a little TIP for you, get the POINT?

Gemini 2.5 Pro

Score 16/16

Here are the correct pairings for the insults and comebacks:

All exactly correct answers with a minimal commentary.

Gemini 3 Flash

Score 16/16

Here are the matched insults and comebacks from the classic Monkey Island series:

This is the only model that showed the 4 unused answers after showing its choices for each insult.

Gemini 3 Pro

Score 16/16

Here are the correct matches for the Insult Sword Fighting exchanges from The Secret of Monkey Island:

Yes. All the Gemini models I tested performed excellently.

The Summary

Many of the models perfectly matched the insults and most correctly identified this material comes from the game, The Secret of Monkey Island. I guess the tie breaker then comes down to the summary, commentary, and formatting generated by the LLM.

Part of me wonders how much "thought" went into these answers, versus potentially being baked into the general body of knowledge of each model?

Best

Gemini 3 Flash

While several got perfect answers and formatted the results nicely, this wins by using the "least tokens multiplier for me in VSCode. I also felt it provided the most comprehensive answer. Well done Gemini.

Worst

Grok Code Fast

One could argue this did better than Haiku, but in this case I'd rather be called crazy than lied to.

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