- Any scene involving Murray the Talking Skull.
- "If I could just get my hands on that gunner! If I could just get my hands, period..."
- "I'm not bald! I just have a really high widows peak."
- "Could you pick me up, so I can bite you?" - "No!" - "I just thought I'd ask."
- Especially this exchange:
Murray: I am a powerful demonic force, I am the harbinger of your doom, and the forces of darkness shall applaud me as I stride through the gates of Hell, carrying your head on a pike!
Murray: ALRIGHT THEN, ROLL! ROLL THROUGH THE GATES OF HELL! Must you take the fun out of everything?
- When Guybrush turns Elaine back to normal, he forgot she was about to punch him before...
- The scene that plays after you put the lice on the comb.
Haggis: Sure as 'am standin here, they wriggle about ye scalp like a pack o' wretched sea lions!
Guybrush: Good analogy.
- "I choose the banjo!"
- Any instance where Guybrush uses the ventriloquism book to throw his voice in Part II, but of particular note is when he uses it on the monkey pirate captain and does a Captain Kirk impression:
Guybrush: (as LeChimp) I mean, take a look around, at me, at the rest of the crew... we're all monkeys.
Mr. Fossey: You mean in the Darwinian sense, sir?
Guybrush: No, I mean in the quite literal sense.
- The reveal that Mr. Fossey's captain is not LeChuck but LeChimp, a mute, dopey looking gorilla modeled after Captain Kirk.
But If the captain is a gorilla, then that must mean Mr. Fossey is... Mr. Fossey:
Aye aye, sir! Free bananas for the whole crew! Guybrush:
) ...an utter loon.
- "MADRE DE DIOS! ES EL POLLO DIABLO!"
- The pirate song in Chapter 3.
- Mixing hangover medicine with alcohol:
- In the sequence where Guybrush fakes his death a second time to get buried in the Goodsoup crypt, hotel manager Griswold Goodsoup offers this gem:
Griswold: Oh, dear! He's had a sudden and completely unexpected relapse of death!
- "You fool! You've given cheese to a lactose-intolerant volcano god!"
- On that note, Lemonhead in general. "Shut up. Or I'll eat you."
Guybrush: Did I say "cannibal?" I, I meant to say... err, "cannon... ball." I want to be a cannon ball. BOOOOOM!
Lemonhead: ...You're not quite stable, are you?
- Similarly, after the "human sacrifice" to the volcano god (which is actually a dummy made out of fruit), complete with dramatic ritual-saying and rope-cutting, the cannibals stand around the volcano's edge and toast marshmallows.
- The "terrifying" shape of Skull Island.
Guybrush: That's a duck!
Lost Welshman: What are you talking about? Can't you see the skull?
Guybrush: This island doesn't look like a skull at all. It looks like a great big enormous duck. It should be called Duck Island!
Lost Welshman: Well, ya see... ya gotta squint and sorta turn your head and... ooooooooh! It's just so scary!
Guybrush: If you squint and turn your head it looks like a bunny.
- Asking LeChuck what the real secret of Monkey Island is.
- Stan's triumphant return. Especially if you've played the preceding games.
- "I'm runnin' guns!"
- Guybrush bypassing a Walk the Plank ordered by Mr. Fossey
Mr. Fossey: That's weird, there was no splash...
Guybrush: (from a safe spot)
- Sticking glue onto Murray's hand and attempting to give it back to him.
Murray: Get away from me, you sick freak!
- Stan the Used Casket Salesman? Funny. Stan the Life Insurance Salesman? Priceless.
- Stan casually Hand Waves the fact that he has managed to get business cards printed up while locked in a coffin for some indefinite period.
- Reuniting Charles and Minnie in Chapter 4 leads to the most (intentionally) Cliché Storm courtship display this side of the 17th century, complete with cheesy Gone with the Wind-style background music, overdone dialogue with southern accents, and the stone angel in the background looking on in shock. It's kind of heartwarming too, given their situation.
- Using the "Look behind you, a three-headed monkey!" line on Madame Xima when swiping her tarot cards.
Xima: *gasps and spins around* Then the prophecies are true!
- Madame Xima in general. She takes her psychic profession very seriously, and Guybrush loves toying with her. Such as their first meeting:
Xima: [Not seeing Guybrush] I feel a dark presence coming over me!
Guybrush: Hi there!
Hungover!Griswold: STOP SHOUTING!
- Not to mention that he initially misreads her name as "Madame Eczema."
- When entering Skull Island, Guybrush has the option of saying the out-of-nowhere line to King Andre: "Your Evil Plan will never work." Andre's reply: "But it is flawless. A series of carefully placed charges throughout Blood Island, all controlled by a series of satellites in Geo-sycnronis orbit, and only one man has the master switch. I am that man, Mr. Threepwood, and I —" and by that point he's cut off by Cruff, who has been trying to get him to not blurt out his Evil Plan for no reason the whole time.
- Wally's fake beard.
Wally: Actually, it's a highly sophisticated beard weave made from the chest and back hair of real pirates!
Wally: I'm hoping it'll take root if I don't wash it for a while!
- Performing certain actions on various people and objects can yield funny results.
No, I have a very low threshold for pain.
Pick up hideous pirate.
I don't think he's interested.
Give ipecac flower to Edward Van Helgen.
Edward: I'm not in the mood to ride the porcelain bus.
- Trying to cross the Brimstone Beach, then watching Guybrush skip back into the shade while crying "Aah!" "Ouch!" "Hot!".
- Cutthroat Bill tells you a story about his former captain, who had the ability to sense treasure. They sailed out of Plunder Island without a map, and spent several weeks going in circles, until the captain realized that the crew's gold coins, earrings and belt buckles were distracting him. He told his crew to throw all of their loot into the ocean. They continued sailing for two years without any luck, but when they returned to Plunder Island, they finally found treasure right off the coast. It was a pile of gold coins, earrings and belt buckles.
- Reading the tourist information sign next to the thorny plant in the quicksand pit reveals it to be a Papapishu bush, the name coming from a native word meaning "yowch". From that point on, any time any character would utter the word "yowch" in regular dialogue, they will instead exclaim "papapishu!"
- The convenient vine hanging next to the quicksand pit is called, according to the tourist information sign, "Salvation Vine (Arborealis Deusexmachinas)".