The Secret of Monkey Island: Special Edition

(Missable)

During the Three Trials section of the game, Guybrush will visit Captain Smirk and learn the art of pirate fighting. As they spar, Smirk will teach you the first two pirate insults to use. Once Guybrush has learned these beginning insults, you should place him in a highly trafficked area on the map (the intersection to the left of the "fork" seems to be the best place to initiate a fight). Once an encounter is started, have Guybrush threaten the pirate by saying, "My name is Guybrush Threepwood, Prepare to Die!" This will be your chance to pick the insults you already have learned, in order to hear the correct responses from the pirates as well as giving you the chance to use the correct responses on the insults they say to you.

At times, the pirates will not give you the correct response and will use a neutral response like, "Oh yeah?" or "I'm rubber, you're glue!" In these instances you will need to use the insult on another pirate in order to learn the correct response. The trickiest and most time consuming thing can be waiting for the last one or two insults to be used by a pirate. I found that once you get down to the last remaining insults to be unlocked, it is best to have Guybrush use the top insults on his turn and use an incorrect response to every insult in order to give each pirate more chances at unlocking the insults you are needing.

The trophy will unlock once you learn the 16th insult. Here is the list in order of how they will appear in your text list:

Insult: This is the END for you, you gutter-crawling cur!
Response: And I've got a little TIP for you, get the POINT?

Insult: Soon you'll be wearing my sword like a shish kebab!
Response: First you better stop waiving it like a feather-duster.

Insult: My handkerchief will wipe up your blood!
Response: So you got that job as janitor, after all.

Insult: People fall at my feet when they see me coming.
Response: Even BEFORE they smell your breath?

Insult: I once owned a dog that was smarter then you.
Response: He must have taught you everything you know.

Insult: You make me want to puke.
Response: You make me think somebody already did.

Insult: Nobody's ever drawn blood from me and nobody ever will.
Response: You run THAT fast?

Insult: You fight like a dairy farmer.
Response: How appropriate. You fight like a cow.

Insult: I got this scar on my face during a mighty struggle!
Response: I hope now you've learned to stop picking your nose.

Insult: Have you stopped wearing diapers yet?
Response: Why, did you want to borrow one?

Insult: I've heard you were a contemptible sneak.
Response: Too bad no one's ever heard of YOU at all.

Insult: You're no match for my brains, you poor fool.
Response: I'd be in real trouble if you ever used them.

Insult: You have the manners of a beggar.
Response: I wanted to make sure you'd feel comfortable with me.

Insult: I'm not going to take your insolence sitting down!
Response: Your haemorrhoids are flaring up again, eh?

Insult: There are no words for how disgusting you are.
Response: Yes there are. You just never learned them.

Insult: I've spoken with apes more polite then you.
Response: I'm glad to hear you attended your family reunion.

These insults serve a second purpose as well, as the responses are needed to fight the Sword Master. She will not be using the same insults but the responses you learned will be used. For informational purposes, I am adding them here to help you with that fight:

Sword Master: I've got a long, sharp lesson for you to learn today.
Response: And I've got a little TIP for you, get the POINT?

Sword Master: My tongue is sharper then any sword
Response: First you better stop waiving it like a feather-duster.

Sword Master: My name is feared in every dirty corner of this island!
Response: So you got that job as janitor, after all.

Sword Master: My wisest enemies run away at the first sight of me! & I usually see people like you passed-out on tavern floors.
Response: Even BEFORE they smell your breath?

Sword Master: Only once have I met such a coward!
Response: He must have taught you everything you know.

Sword Master: If your brother's like you, better to marry a pig.
Response: You make me think somebody already did.

Sword Master: No one will ever catch ME fighting as badly as you do.
Response: You run THAT fast?

Sword Master: I will milk every drop of blood from your body!
Response: How appropriate. You fight like a cow.

Sword Master: My last fight ended with my hands covered with blood.
Response: I hope now you've learned to stop picking your nose.

Sword Master: I hope you have a boat ready for a quick escape.
Response: Why, did you want to borrow one?

Sword Master: My sword is famous all over the Caribbean!
Response: Too bad no one's ever heard of YOU at all.

Sword Master: I've got the courage and skill of a master swordsman!
Response: I'd be in real trouble if you ever used them.

Sword Master: Every word you say to me is stupid.
Response: I wanted to make sure you'd feel comfortable with me.

Sword Master: You are a pain in the backside, sir!
Response: Your haemorrhoids are flaring up again, eh?

Sword Master: There are no clever moves that can help you now.
Response: Yes there are. You just never learned them.

Sword Master: Now I know what filth and stupidity really are.
Response: I'm glad to hear you attended your family reunion.

Please remember: You will not be able to respond to the Sword Master's insults with these responses, if you never learned them from the pirates so it is useful to finish all 16 insults and responses before moving on each time you play. For speedruns or impatient players who already have achieved the trophy, you will be able to get by not knowing up to two of the responses and may still best the Sword Master to continue the story if needed.