- Guybrush Threepwood: How much wood could a woodchuck chuck if a woodchuck could chuck wood?
- Woodchuck: A woodchuck could chuck no amount of wood since a woodchuck couldn't chuck wood.
- Guybrush Threepwood: But if a woodchuck could chuck and would chuck some amount of wood, what amount of wood would a woodchuck chuck?
- Woodchuck: Even if a woodchuck could chuck wood, and even if a woodchuck would chuck wood, should a woodchuck chuck wood?
- Guybrush Threepwood: A woodchuck should chuck if a woodchuck could chuck wood, as long as a woodchuck would chuck wood.
- Woodchuck: Oh, shut up!
- [Looking at a bust in Elaine Marley's room]
- Guybrush: You know I heard some guys talking about Marleys bust, this must be it.
- Herman Toothrot: If a tree falls in the forest and no one is around to hear it, what color is the tree?
- [the player must now go through 40 or so answers before finally being allowed to select:]
- Guybrush: All colors?
- Herman Toothrot: Exactly. Now, what has this experience taught you?
- Guybrush: That philosophy isn't worth my time.
- Herman Toothrot: I'm very impressed. It takes most people years to reach this point.
- Guybrush: If I could just reach my pirate utility belt...
- [Guybrush is being mugged by Largo LaGrande]
- Guybrush: HEEELP! Police!
- Largo: HA! Scream all you want, there are no police on Scabb Island.
- Guybrush: Then who eats all the doughnuts and roughs up the transients?
- [after finding out LeChuck will be brought back to life]
- Guybrush: He's going to come after me!
- Voodoo Lady: Yes.
- Guybrush: He's going to try to kill me!
- Voodoo Lady: Undoubtedly.
- Guybrush: Can you just kill me now and get it over with?
- Rapp Scallion: Now I can finally rest within the fold of the earth... like a Steamin' Weenie on a hot bun.
- Largo LaGrande: You're not from these parts are ya? This here's a toll bridge you've got to pay.
- Guybrush: Is this some sort of bribery situation?
- Largo LaGrande: No more like extortion, here allow me to demonstrate.
- [Picks up Guybrush and holds him upside down over the side of the bridge]
- Lechuck: Largo you've been my trusted henchman for many years but I will not hesitate to drag your entrails from the back of my ship if you do not bring me Guybrush Threepwood before he finds that treasure!
- [after Governor Phatt has said that LeChuck is offering a large bounty for Guybrush's capture]
- Guybrush: I bet that money could buy a lot of bacon grease and pure fat, huh?
- Guybrush Threepwood: I'm on a whole new adventure.
- Bart: Growing a mustache?
- Guybrush Threepwood: No. Bigger than that.
- Bart: A beard?
- Largo LaGrande: You're making me mad, Marty.
- Mad Marty: That's my name, don't wear it out.
- Guybrush Threepwood: Do you like my new beard?
- Voodoo Lady: There's only one way to escape from Lechuck.
- Guybrush Threepwood: How?
- Voodoo Lady: You're doing it right now.
- Guybrush Threepwood: Fiddling with the change in my pocket?
- LeChuck: I... am your brother!
- Guybrush Threepwood: No! No, that's not true!
- LeChuck: Search your feelings, you KNOW it to be true!
- Guybrush Threepwood: Noooooooooooooooooooo!
- Guybrush Threepwood: Hey, dynamite... just like it says on the side!
- Voodoo Lady: Two, four, six, eight, who do we assassinate? Largo, Largo, yeah!
- [LeChuck has captured Guybrush and Wally and explained them the intricate torture mechanism]
- LeChuck: Do you know what happens next?
- Guybrush: Umm... Well...
- LeChuck: I will then take your bones, still alive and in great pain, and make them into a chair. I will call it "My Screaming Chair". Every day I will sit in it and listen to you scream. Any questions?
- [LeChuck soon gets tired of Guybrush's stupid questions and leaves the scene]
- Wally: He didn't say what he was going to do to me!
- Guybrush: An ottoman comes to mind.
- Rapp Scallion: Violets are blue. Roses are read. We're coming aboard. Prepare to eat lead.
- Guybrush Threepwood: Leg or no leg, I trust you about as far as I could throw Manhattan.
- [to LeChuck]
- Guybrush: Have you ever tried conditioner on that beard?
- [while hanging over a pit of acid]
- Guybrush: Wally?
- Wally: Yeah?
- Guybrush: Could you scratch my nose?
- Wally: Yeah, right after you kiss my butt.
- [Using Voodoo doll on Largo]
- Guybrush: Take that you stumpy little dim-witted toad!
- [to Elaine Marley]
- Guybrush: So? You and the gardener, eh?
- Guybrush: They don't call me the Bone Master for nothin'!
- Guybrush Threepwood: She named the dog Guybrush?