I think the best one was Thoruk, my Barbarian (who I'm very proud of).

The setting: The band had been asked to clear out a dwarven homestead full of Kobolds, and Thoruk went full-rage on them, scattering them as he went. He was faced by 2 routes, and I rolled randomly as a raging thoruk (intelligence 8) wouldn't care much for decision making. Turns out that the room I went into was a shrine, and I foolishly said "I'll smack whatever's closest with my sword, then go back", expecting to just break a chair or something. Nope, DM decides the closest thing's an alter, and I smack it one with my dragonsword. one contested strength test later (intended to throw Thoruk back akin to Gimli trying to break the one ring) and I roll a nat 20, and overpower the alter, cracking it in half.

This (naturally) leads to the embodiment of the Dwarven Goddess of protection appearing and trying to give Thoruk a talking to about his antics. As she approaches, Thoruk (seeing she has a neatly trimmed beard) holds out his hand and says (to this swirling apparation of a dwarven goddess who wasn't there 3 seconds ago):

"Stay back sir; there could be more." and charges further into the house.

Thoruk then was grabbed by the Goddess, who asked him what in the blue blazes he thought he was doing. Thoruk replies that he was told by the (Dwarven) owners of the house to go in and "destroy everything". When asked to roll Deception, I argued that Thoruk honestly believed this, so we agreed instead to roll Persuasion. Natural 20. He persuaded the goddess of protection of the home that the homeowners wanted him to smash her alter. All because he wasn't really listening when he was told what to do.

I must say, Thoruk is awfully good fun to roleplay as.

That's freaking hilarious. XD

A goofy bit of an OOC conversation I had with one of my players last night:

Morrigan's Player: Yeah, Morrigan will probably pass then. She'll visit them on the way back. (If she doesn't do anything stupid and die before then, at least) Also, what does Morrigan know about her home country?

Me (DM): You better survive. XD Ah. Good question. Let me grab those notes.

Morrigan's Player: I would say "You don't get to say that, you're not Morrigan's mom," but as the DM, you technically ARE her mom, AND her dad XD

Me (DM): I'd give you a real life inspiration point for that, if it were possible. XD

Dm: " A giant butt monster ate your gold coins "

Wizard " I climb in the giant butt monster and get the coins back "

Dm " Roll a DC 10 Dexterity Check to get out "

Wizard " I rolled a 3 "

Dm " You are trapped in a giant butt monster "

I ... honestly have no response to that.

I think you may have on of the funniest quotes in this thread.

innkeeper, wondering how to dispose of a dead NPC: "okay, does anyone here know how to dispose of dead bodies?"

My rogue/barbarian bounty hunter Goliath: "how hard to find do you want it to be?"

innkeeper: "...please leave."

(for those wondering, it was a fire that our party did not cause. If anyone can think of a shape changer with the death burst trait, please notify)

Bonus quote:

Me, OOC: "so I'm a barbarian-rogue multiclass. Trust me, it actually works pretty well. I also plan to take a level in wizard."

A hodgepodge adventuring team encounters a hag coven and things go sideways real bad.  The hags unleash their Hangman's Tree and it immediately starts attacking the group's paladin. 

The level 1 Bard (who just joined the group) rises to the occasion.  "Hey tree!  Your bark is worse than your bite!" (No other action but to taunt the massive, possessed tree)

(The poor, brave bard was strung up in vines the next round and spent the rest of the fight hanging KO from the tree.)

Quote from Bartjeebus >>

 

A hodgepodge adventuring team encounters a hag coven and things go sideways real bad.  The hags unleash their Hangman's Tree and it immediately starts attacking the group's paladin. 

The level 1 Bard (who just joined the group) rises to the occasion.  "Hey tree!  Your bark is worse than your bite!" (No other action but to taunt the massive, possessed tree)

(The poor, brave bard was strung up in vines the next round and spent the rest of the fight hanging KO from the tree.)

 That's dark.  Really dark.  Bard needs some chocolate for that.

A summing up of something that is a role-play thread, started by my character:

Me: We all have things we regret.

Other guy: I don't!

Me: Didn't you kill a bunch of gods?

Other guy: Yes, but I didn't regret that. Everything in my life has had an enjoyable consequences.

This one was from my last PC in Descent into Avernus. Probably the funniest moment in any campaign I've played.

So we're in Hell and fighting a bunch of devils. We get the bright idea to push one into a pool of demon ichor because the fight isn't going our way and we know demon ichor is dangerous stuff. 

While RP'ing, one party member sarcastically asks "What's next?! Are we 'gonna give them f***ing wings?!" because we've accidentally swung the battle in their favor with some bad decisions. 

I cast a spell that forces one devil into the ichor and the DM rolls on a table to determine what happens. DM begins laughing really hard and narrates that the ichor's effect caused the devil to sprout functional wings, one on either side of it's head.

*party erupts with laughter*

Devil flies out of the pool while cackling at us as the sarcastic PC is cry laughing with all of us and he's trying to RP "OH, F***ING GREAT! NOW YA DID IT! AMAZING...JUST WHAT WE NEEDED!"

I slap Harold.

Roll for damage.

(harold has one 1 hit point)

Warforged paladin speaking to anti-warforged activist:

You're right in one thing. I am an but an instrument. An instrument of divine justice and wrath.

Hags: “Who sent you?”

Rogue: “A friend.”

Hags: And what was his name -“

Paladin: “My deity. My deity sent us.”

Rogue: (at the same time) “Arthur Dent!”

Paladin: (panicked) “My deity’s name is Arthur Dent!”

(in a different campaign with different characters several months later)

Sorcerer: “Arthur Dent! Save us!”

Also, in an Eberron campaign:

Psi Knight (OOC, describing his appearance): He was at one point a normal (I forget what race he was), but because daelkyr are weird, he has -

Evil Bard: Multiple eyes?

Psi Knight: No, purple skin.

Bard (now in character): Are you sure? Because I’m a collector.

Someone (I forget who): Of WHAT?

Bard: Lots of things. Mysterious glowing orbs... I work for a museum.

Wizard: But eyes?

"All right, it's time to initiate Operation: Totes M'Goats."

"You're acting like this thing is your child, when it's probably 400 years older than you."

"Execute Operation: Innocent Lad"

Quote from Maelstrom51210 >>

"All right, it's time to initiate Operation: Totes M'Goats."

"You're acting like this thing is your child, when it's probably 400 years older than you."

Quote from Cindrellic >>

"Execute Operation: Innocent Lad"

 Both of these need additional context.

Rogue: If you think about it, the throat is just the butt higher up.

Artificer: Yeah, all animals are really doughnuts.

Blood Hunter: Or straws.

“Why do I have to do everything myself!?”

“You really don’t. The rest of the party has been dealing just as much damage.”

”....true.”

Paraphrased:

Barbarian: "...the Giant I single-handedly killed--"
Rogue: "--Excuse me?!"
Barbarian: "...that I nearly killed singly-handedly but gave you the glory..."
Rogue: "Okay. I'll accept that."