Winslow's man-crush on Guybrush ("I like it when you point at the map"), LeChuck's attempt at solving an adventure game puzzle, Coronado De Cava's obsession that Guybrush has a thing going with the Voodoo Lady, Guybrush possessing the Voodoo Lady and not only enjoying her "physics" but also finding out why she "never stands up when I'm around", De Cava's crew's obsession with the rather-dead Santino (and the discovery that he was the most awesome person in the crew), Murray's political turn, two pirates squabbling over who gets to bury the treasure, De Singe's obsession with amputation, "Pirate Spunk", a spin on insult swordfighting where you have to help a manatee hook up with a bloodthirsty female, McGillicutty's "torture" technique, and of course, Murray's commentary over the end credits of Leviathan... and we're only 3/5 of the way through!
Speaking of the manatees...
Guybrush: This is satisfactory.
Manatee: Stop saying that!
There's usually one of these right at the end of the lukewarm open. Of special note is Chapter 1's:
Guybrush: "This'll be a snap. *tries snapping* A snap. A sna- (poxed hand punches him in the face) OW!"
Guybrush pretending to sacrifice the Pink Pajama Pierre Porcelain Power Pirate figurine at the altar in Chapter 1.
Also funny is when he does that pretend voice while dipping the figurine in a vat of ink. "Sacré bleu! Eez zis ze end of Pink... Pajama... Pierre? Glug!"
Also, Guybrush distracts De Singe on the last wind idol so he finds a way to have De Singe blast himself sky-high and onto the idol. You can even hear De Singe yelping in pain as Guybrush rotates the idol until the correct facial part-matching makes him sigh in relief.
Not to mention Guybrush's reaction if you attempt to use the weather vane like you do with the other idols.
Guybrush: Oh, I'd love to, but I'm pretty sure that De Singe doesn't have the necessary... slots.
When Guybrush is looking around the Voodoo Lady's shack for the first time in Chapter 1, he sees a closet. When he goes to open it:
Guybrush: Wonder what's in here—?
Voodoo Lady: Don't touch that! It's where I keep my...unmentionables.
[Guybrush shudders in fear and disgust]
If you move the pointer over the closet again, it's title will have changed from "Closet" to "The Scariest Closet In The World".
"Nice cans. ...I mean, nice cans."
Of all the options available during the swordfight at the beginning of episode 2 of Tales Of Monkey Island, few are as satisfying as inspecting the ship's mast. Repeatedly.
During the sword fight with Morgan at the beginning of Chapter 2, Guybrush tries to distract her:
Guybrush: Look behind you, a giant three headed sea chimp! Morgan: No thanks, I already had lunch. Guybrush: Eewww...that's just taking it too far.
Having to walk LeChuck through a particularly simple puzzle. Especially if you've used the SCUMM interface of the earlier games. "Use... breath mints... yourself."
"Use... claw thingie... yourself."
McGillicutty trying to make Chieftain Beluga talk.... by trying to drown him/her. Beluga is a merperson. The best part is Beluga constantly telling him that it won't work.
The alternative questions you can ask Chieftain Beluga instead of asking how to use the summoning items:
Guybrush: Can I have a cookie? Beluga: You cannot. Guybrush: I'm sorry, may I have a cookie? Beluga: You may not. Guybrush: Cookie? Beluga: No.
Guybrush: You wouldn't happen to know the secret of Monkey Island, would you? Beluga: I know the secret of Donkey Island if that helps. [Beluga leans in and whispers in Guybrush's ear] Guybrush: Eew, no!
Murray. Just Murray.
In Episode 3, when Guybrush "kills" the clearly dead and skeletonized Santino by cutting Murray off his shoulders to intimidate the crew... and it works.
In Chapter 3:
Guybrush: Seabiscuit!!! [runs and takes an actual sea biscuit near the seahorse head] Mmm... I love these things. [eats up the biscuit, then gasps in surprise] And a seahorse head!
The whole monkey scene with Elaine and LeChuck in Chapter 3. Still gets us every time!
Another one from Chapter 3: the "Pirate Face-Off" scene is funny on its own, but it's even funnier with the subtitles on, as the growl each pirate makes when showing their face is subtitled as *[Name of last expression] SOUND*. (e.g. *GEEZER SOUND* or *MEANIE SOUND*
From episode 4, add any time Guybrush and his lawyer interact with each other. As well as any time the judge gets angry. "The defendant will stop pretending he knows how to speak Latin!"
And Episode 5, despite being the Darkest and Edgiest episode yet, has the sequence where Guybrush taunts Bugeye, just about any conversation with Galeb, and the revelation of what happened to Guybrush's corpse.
LeChuck in his speech to Elaine near the end of Chapter 5: