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Are there more than one possible reply to the insults? I vaguely remember playing Secret of Monkey Island a long time ago and ending up in a sword fight against either a pirate or the sword master, unfortunately can't remember which one. They threw an insult at me which I didn't have the correct counter-insult for yet, so I replied with another one that was kind-of fitting. And won the match despite using an "incorrect" reply.

EDIT: I'm not sure if the insult was this one, but this is what I mean:

Insult: Only once have I met such a coward!
Reply: He must have taught you everything you know.
Alternative reply: I'm glad to hear you attended your family reunion.

I don't currently own a playable version of Monkey Island so I can't verify if they work myself.

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How appropriate, you fight like a cow. – Jonathan Drain Dec 19 '11 at 12:32

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Yes, some of the Sword Master's insults have multiple valid comebacks. I just tested these on the Special Edition, but they should work in the original game as well.

Insult: Only once have I met such a coward!
Comeback #1: He must have taught you everything you know.
Comeback #2: I'm glad to hear you attended your family reunion.

Insult: I usually see people like you passed-out on tavern floors.
Comeback #1: I'm glad to hear you attended your family reunion.
Comeback #2: Even BEFORE they smell your breath?

Insult: My name is feared in every dirty corner of this island!
Comeback #1: So you got that job as janitor, after all.
Comeback #2: Too bad no one's ever heard of YOU at all.

Insult: My last fight ended with my hands covered with blood.
Comeback #1: I hope now you've learned to stop picking your nose.
Comeback #2: Your hemorrhoids are flaring up again, eh?

There might be more, but those are the ones I could find. I don't think any of the "regular" insults have multiple comebacks, though.

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And I've confirmed this is true on the original edition of the game. Good job with the research! – Jason Berkan Dec 20 '11 at 4:00
Brilliant, thank you! – Kaivosukeltaja Dec 20 '11 at 8:35
up vote 5 down vote

The insult sword fight quests in Monkey Island and Monkey Island 3 both follow the same routine: collect insult and counter-insults from various foes until you have a wide enough repertoire of counter-insults to battle the "insult boss". The "boss battle", so to speak, is what you roughly describe, he throws insults at you which you never heard before, but you can counter them with counter-insults you know from previous battles, but still fit the boss' insults. (in the case of Monkey Island 3, they always rhyme, which makes finding out the right answers a bit easier)

One thing to note though, while you can counter those "boss-insults" with your known counter-insults, if you try using the same insults on lesser foes, they'll reply that you're unfair by using those insults and won't be able to respond, it's up to you to find which of your counter insults fit.

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Thanks for the answer, but what I'd like to know is if there's more than one possible answer to some of the insults. – Kaivosukeltaja Dec 19 '11 at 12:55
As far as I recall, and I played both games several time through, no there wasn't, answer either fit their original insults or their boss-insults, but not different insults by the same guy. – JohnoBoy Dec 19 '11 at 13:00

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