* The dragon the Devourer cult is using to freeze up Korthos is being controlled by a mind flayer named Drastix Achthend. In Draconic, this translates to [[HoistByHisOwnPetard "dragon food."]]
** Even better, when you finally destroy the artifact that is allowing the flayer to control the dragon, the Dungeon Master notes that the dragon looks "[[{{Understatement}} very annoyed]]" as she [[LiterallyShatteredLives turns Drastix into an illithid popsicle with her ice-breath]].
* The person that respecs your feats is named... Fred.
** And he's a ''mind flayer''. When your character [[LampshadeHanging points out how odd this is]], he explains that it was the name of his first customer, and that [[YouCannotGraspTheTrueForm his real name is unpronounceable]].
* The quests Delirium and Acute Delirium(which take place in the same inn) are full of these moments. Due to interaction with creatures from Xoriat, the realm of madness, you: [[spoiler: teach a key a lesson, have a drinking contest with beholders, fight hambies(zombie ham), can grief an Elder Beholder that wants to solve a tile puzzle, fight puzzle tiles, escort beds and bookcases to form an airship, travel to Xoriat in the airship while holding off beholders from boarding said ship, and going into a giant beholder to receive the scepter that caused all of this.]]
** You forgot the best part: [[spoiler: to escape said giant beholder you have to make him puke you and your party back up.]]
** Also, the dialogue from the mimic that ate the scepter, the Dungeon Master, and the beholders make this quest even more hilarious.
* In the quest Siegebreaker, there's a rest shrine located in a disgusting pool where the enemy have been using it as an open air bathroom. If you're not careful and fall in, you get hit with a debuff called "What's That Smell?". And the ledges around it are VERY small.
** In the same quest, detonating the Droaam bombs spawns two optional minibosses, a kobold and an ogre named [[PinkyAndTheBrain Brinky and Pain]] respectively. Their dialogue ends with:
--->'''Pain''': What are we going to do now, Brinky?
--->'''Brinky''': The same thing we do every day, Pain. [[ShoutOut Take over the world!]]
** Yet another one from Siegebreaker; there is a (rather fat) half-orc miniboss named Skinny. He's the cook, and has an attack called Frying Pan in Face, complete with sound effects, a brief stun effect, and [[BreadEggsMilkSquick about twelve points of damage]].
* All of the Kobold dialogue in the Challenge Packs.
* Otto's Sphere of Dancing . It's a disco ball floating in the air that....................makes nearly everything break into dance. It lasts up to 80 seconds.
* From general chat:
--> No amount of alcohol will help you forget ''[[ThatOneLevel The Pit]]''
* From Irrestone Inlet, when you kill the boss, Yaaryar "Yaaryar shrieks furiously, '[[WeWillMeetAgain I'll kill you! Kill you all...]] grrghh....' [[DeadpanSnarker Then he dies, effectively calling his own bluff.]]"
* Named monsters sometimes have a BossSubtitles under their names. In a challenge, one is Ugg <[[DumbMuscle Confused Meatshield]]> and the other is Dr Will Eve Rushmore <[[SmallNameBigEgo Renegade Master Wizard Himself]]>.
* The Bargain of Blood quest from the Sentinels of Stormreach pack has some pretty hilarious moments. You turn an open air tavern into a warzone, with a fireball happy wizard, a meatshield swinging a big sword/axe... And the [[UnfazedEveryman tavern patron]] just [[UnusuallyUninterestingSight just wonder where the waitress went]] (she hit the deck).
** And the Magic Mouths advertising for the service the pirate run bazaar offers. Some try to sound legitimate but are blatantly transparent as to the criminal origin of the goods, other just straight up tell you they set up a slave trade... All are just hilarious.
* The end "fight" of Partycrashers if you complete ''all'' the optional objectives is hilarious.
--> '''Lokael''': "Ahh, so you're the famous Viceroy of House Phiarlan. I notice you've emptied your cup -- you really liked that drink, didn't you? Too bad for you it was POISON! Baw-ha-ha-ha!"
--> '''Cyan''': "I'm afraid your Poisonmaster didn't live to touch the Viceroy's cup... tragic accident in the Library, all those paper cuts...."
--> '''Lokael''': "Touche! But, I always have a backup plan... like BRAINWASHING your own guards to kill you! Baw-ha-ha-ha!"
--> '''Cyan''': "I'm afraid the guards aren't coming... they're too busy burying the corpse of your Spellmaster."
--> '''Lokael''': "Impressive... but I always have a backup to my backup... such as a full TROUPE of Cabal assassins, hidden right under your nose, BAW-HA-HA-HA!"
--> '''Cyan''': "You mean the Tieflings in the upstairs private rooms? I'm sorry, they didn't have invitations, so I had them... flushed."
--> '''Lokael''': "What? All my wonderful plans... ruined...."
--> '''Cyan''': "(Bluff) There, there, it's been a terribly hard day for you, hasn't it? Here, have a drink and try to relax."
--> '''Lokael''': "(Gulp, gulp) Ugh, my stomach...." *collapses*