Elaine Marley: Let’s face it, LeChuck. You are an evil, foul-smelling, vile, codependent villain and that’s just not what I’m looking for in a romantic relationship right now.
LeChuck: Darn yer riddles, ya saucy female! What d’ya mean?
"I can’t, I’m washing my hair tonight"
– Elaine Marley, reply to LeChuck asking her to be his undead wife
[Guybrush encounters a talking skull, floating in the water.]
Guybrush: Can I call you ‘Bob’? (Referring to the undead pirate Bob from the first game whose skull kept falling off, also possibly a reference to an old joke about what you call someone with no arms and no legs in a swimming pool.)
Murray: You may call me ‘Murray’! I am a powerful demonic force! I am the harbinger of your doom! And the forces of darkness will applaud me as I stride through the Gates of Hell – carrying your head on a pike!
Murray: All right then, roll! Roll through the Gates of Hell! ... must you take the fun out of everything?
[Guybrush manages to swim back to shore, where Elaine is still scanning the water looking for him.]
Elaine: Guybrush? Guybrush... I thought I'd lost you forever! Is it really you?
Guybrush: Yes, Elaine! Um... Did you really mean what you said out there? That I was the only man you ever loved?
Elaine: Uh, well... yes Guybrush... I guess I did.
Guybrush: Elaine, I'm a man of action. A swashbuckler. A rogue. A wanderer. A man who can hold his breath for ten minutes. I have no ties and no regrets; I sail with the wind and go wherever adventure takes me. But somehow, something always leads me--
Elaine: Guybrush, stop babbling.
Guybrush: Elaine... will you marry me?
Elaine: Oh, Guybrush!
[Guybrush, tarred and feathered so he looks like a man-sized chicken, enters Blondebeard's chicken shop.]
Captain Blondebeard: ¡Madre de Dios! ¡Es el Pollo Diablo! (“Mother of God! It’s the Devil Chicken!”)
Guybrush: ¡Sí! ¡He dejado en libertad los prisioneros y ahora vengo por ti! (“Yes! I have released your prisoners, and now I've come for you!”)
Captain Blondebeard: Well, yer not takin’ me without a fight!
[Blondebeard bashes Guybrush over the head with a frying pan]
“I’m not bald! I just have a really high widow's peak.”
– Murray, the demonic talking skull
Guybrush: You’re about as fearsome as a doorstop.
Murray the demonic talking skull: Is it a really evil-looking doorstop?
Guybrush: Never mind.
[Guybrush finds Murray hanging from a tall spike.]
Guybrush: How’d you get all the way up there?
Murray: Through sheer force of will!
Murray: … Okay, it was a bunch of those weird voodoo kids. They found me on shore and put me on top of this spike, all the time thinking they were so funny.
Guybrush: What do you know about lifting voodoo curses?
Murray: Oh sure. I know a lot about lifting curses. That’s why I'm a disembodied talking skull, hanging on a spike, in the middle of a swamp!
Guybrush: You sound bitter.
Murray: I’m sorry, it’s been a rough day.
Guybrush: If I gave you your arm back, what would you do with it?
Murray: I’d terrorize the South Seas! I’d torture the living! I’d demolish the… er… What I meant to say was, I’d use it to pet kittens.
Guybrush: Nope. You blew it.
"Mine is the name pirates fear the most: Edward “Snugglecakes” Van Helgen!"
Carla the Swordmaster: Do you have any idea how difficult it is to escape from Monkey Island?
Guybrush: No, how difficult is it to… (with emphasis)Escape from Monkey Island?
Carla: Well… it's really difficult.
Guybrush: How does Pegnose Pete smell without a nose?
Bait Shopkeeper: Awful!!!
Guybrush: I should've seen that coming...
“Life is like pillaging a trading vessel bound for Jamestown... Ya never know what you're gonna get.”
– Guybrush sitting on a bench on Lucre Island, in reference to Forrest Gump
“Ahh, the middle finger, the most communicative of fingers.”
– Guybrush, when looking at the middle finger of the giant hand in the Voodoo Lady's shop
“I may be a dunce, but at least I'm a mighty pirate dunce!”
– Guybrush, after getting himself kicked out of the pirate re-training school on Knuttin Atoll
“Are you sure we can't kill him? I’ve let him alive before, and it’s always been a big mistake.”
– LeChuck, about Guybrush Threepwood
“Well… you fight like a cow!”
– Guybrush, when LeChuck exits the Governor’s Mansion
“Get that thing away from me, you twisted freak!”
– Murray, when Guybrush shows him the “Abomination of Nature”
“SEE souvenirs of Guybrush Threepwood’s most famous escapades! TASTE culinary delights approved by genuine pirates! HEAR beautiful pirate folk music! FEEL your souls being gently ripped from your bodies by this restaurant of uncompromising EEEEEVIL!!! MWAH-HAH-HAH-HAAA!!!”
“Oh, the temperature’s a-rising while my sweat’s a-vapourising and I can not feel my legs below my knees anymore.”
– Guybrush, waiting for the ride in the First Church of LeChuck to begin
"Iron Maiden! Excellent! ...Uh, I have no idea why I said that."