Right at the beginning, Guybrush is telling his embellished tiresome old stories.
Guybrush: and then LeChuck cries, "Guybrush! Have mercy! I can't take it anymore!" Pirate 1: I think I know how he must have felt. Pirate 2: Yeah, if I hear this story one more time, I'm gonna be crying myself.
The "how much wood could a woodchuck chuck" conversation between Guybrush and a carpenter.
Guybrush: How much wood could a woodchuck chuck if a woodchuck could chuck wood?
Woodsmith: A woodchuck would chuck no amount of wood since a woodchuck canít chuck wood.
Guybrush: But if a woodchuck could chuck and would chuck some amount of wood, what amount of wood would a woodchuck chuck?
Woodsmith: Even if a woodchuck could chuck wood and even if a woodchuck would chuck wood, should a woodchuck chuck wood?
Guybrush: A woodchuck should chuck if a woodchuck could chuck wood, as long as a woodchuck would chuck wood.
Woodsmith: Oh, shut up.
And the Call-Back to this is equally hilarious when Guybrush asks LeChuck, who cuts him off and answers "Seven cords."
The Wanted Poster on Phatt Island, especially towards the end of the game.
WANTED: Guybrush Threepwood: For the murder of G. P. LeChuck, and also for the use of witchcraft on the person of Largo LaGrande, the thievery of clothing and medically-prescribed hair supplements for such witchcraft, graverobbing, trespassing, larceny without a permit, disturbing the peace, illegal gambling on a sporting event, use of falsified identification for the purchase of alcohol, exceeding allowable FDA limit for rodent parts in vichyssoise, premature entombment of a non-dead individual, reckless tampering with city-maintained plumbing without prior acquisition of environmental impact report, transportation of animals not in a mental state to give consent, vandalizing a historical miniature, reckless use of gardening tools, impersonating a woman in order to evade prosecution, two counts of unauthorized exiting from a penal institution, impersonating a federal mail boat, reanimating dead persons within city limits, possession of library books not specifically checked out to oneself, mixing drinks without a liquor license, and releasing a dangerous reptile in a populated area.
Also wanted for questioning regarding the disappearance of prescription eyewear.
Guybrush lighting the match in the dark room of LeChuck's fortress. And the explosive aftermath.
Use a bucket on the swamp on Scabb Island, and you'll receive a Bucket O' Mud, as well as this gem of a quote:
Guybrush: Wow...A whole Bucket O' Mud...And it's MINE! ALL MINE!!!
To build a Voodoo Doll to use on Largo, Guybrush needs to locate personal items of his, including "something of the head" (Scalp flakes), "something of the thread" (An article of clothing), "something of the body" (Errant saliva), and "something of the dead." (The bone of a deceased relative.) What ends up being Largo's "something of the thread"? A pearly white bra.
Stan and the coffin. It would be reprehensible if it weren't Stan. Even then, it's still kind of a dick move, but at least it sets up a nice Brick Joke for the sequel.
The part in LeChuck's fortress where Wally and Guybrush are hanging marks one of the few times where death is actually possible. If you wait too long, the trap is set off, with Guybrush and Wally sent to their doom screaming in pain (the voice acting in the Special Edition only makes this even more hilarious). Of course, by this time you've forgotten Guybrush is actually reciting how he made it to where he is, which leads to Elaine lampooning him for trying to convince her that he actually died.
Before that, when LeChuck is explaining how his needlessly complicated machine works, Guybrush can ask, "Why didn't you just shoot me?" LeChuck will respond "Because we had an extra disk."
In the original version, examining most objects will yield the description "Nice [Name of Object]", resulting in hilarious sentences like "Nice Bart", "Nice Fink", or "Nice Voodoo key to jail". The Special Edition has Guybrush saying 'Nice' without any modifiers but in an array of different inflections, which can lead to hilarity.
Easily missed. When Guybrush is taken to Governor Phatt's mansion, at one point Phatt will swallow the flies surrounding him when he is fed by his tube machine.
"We can't go there, mon. That's the Forbidden Ovoid."
"We can't go there, mon. That's the Forbidden Elliptic Hyperboloid."
Trying to pick up Captain Kate. She has plenty of lines and comebacks on par with the best swordfighting insults.
Guybrush: You'd be in good hands with me, baby. Kate:You can go bein your own hands, creep. GB: Let's get out of here and go someplace we can talk. Kate: Preferably long distance. GB: Come here often? Kate: Once TOO often, obviously. GB: You know, I could really fall for a girl like you. Kate: Hopefully off a cliff. GB: This ship is so small the rats leaving it are humpbacked Kate: The guy who writes your lines is as funny as your tailor.
The back cover of the game advertises that the game has an "optional easy mode for beginners and magazine reviewers."
It's a bummer in-game, but having Guybrush starting rich just to lose it all in his very first move is an audacious but hilarious way to kickstart the game. Of course, if you go in one direction, reload, and choose the other direction, Largo still mugs you.