Every adventure involving the Pirate Penguins is likely to have at least one crowning moment of funny, with some of the best being Captain Tusk's quotes:
Tusk: Men of the sea have both good and evil otters in their hearts!
Tusk: Penguins, stir up that peanut butter in yer heads and think. This ship here easily weighs 3,000 Du'Inkes. Now why do ye suppose the ship doesn't just sink into the sea? Spirit. It be the spirit of us men of the sea. My spirit be 100, and ye penguins' are about 1.
Tusk: I don't care! All we have here are some penguins and a siren... And I'm some sort of sea mammal.
Gilbert is pretty funny in and of himself, but combined with the penguins he's comedy gold:
Gilbert: Ooohhhh, penguins are craaaanky because they don't haaaaave girlfriends....
Tusk: Make him walk the plank.
In "Two Pearls" when Elazul tries to open the door of fate at the Tower of Lieres and his memories aren't enough to open it, he claims that the door can only be opened by those who is close to the person behind it; when the player character simply barges through the door with zero effort, its funny imagining what his thinking at this point.
In "The Blessed Elixir", you fight Niccolo early on while he's drunk. Practically anyone else with you seeing how the barrel in a soul gets water looks at it in silence. If you have Niccolo along when you head to the oasis (noted to not have an well seen route of a small fork), a different dialogue is triggered with the nuns' elation that you caught the culprit as well. Niccolo grumbles in the end.
Watts when he was victim to Niccolo's cons while he was busy. Watts insists that they get gator skin so he can get his money to 'pay' Nicollo back. Niccolo is baffled at this. And pretty much expected it by the end you got the gator skin from him (either by a reward in "Diddle's letter", item grind like crazy on the only enemy that drops it, or just go to Miss Yuka who gives you free gator skin when you don't have any for that.)
The Remaster has a new animated opening with a couple of moments: Pearl is wandering through the jungle and Elazul is behind her, hilariously uncomfortable in the heat and humidity while Pearl is just fine. Also, Inspector Boyd is shouting at Niccolo while Sandra is casually waving to him from the background.
The Teardrop Crystal anime
Episode 2: When Niccolo try to say hello to Shiloh, the latter retort, saying that he didn't recall that Niccolo is his business friend. Shiloh didn't forget about what happened back thennote the event of "Niccolo's Business Unusual" quest in the game. and demanding Niccolo to give back the 300 Lucre. Predictably, Niccolo run away, saying that goods are non-returnable.
