Funny DnD moments

[Jorin]

Hello all, I'd like to share one of my greatest DND moments with you.

Me and the party were investigating this town for evidence on a evil cult. Our entire party consisted of very charismatic PC's being three tieflings of different classes and one human bard.

Our bard decides to cast detect magic using his lute and begins to skip through town as a traveling entertainer for the kids.

Being the mischevious tieflings, we skipped along casting Thaumaturgy while doing jazz hands causing all the doors and windows nearby to open and shut along with the tune.

We attracted a lot of attention to say the least.

[Buji]

One of our groups is full of funny/stupid moments.

First off, most of this is done by our Cleric, or by me (a Druid) and the Cleric.

Second, our DM likes to homebrew stuff and base things on anime, games, and movies, and he likes doing stupid stuff 70% of the time.

Our Cleric, named Abraxis, is Chaotic or Neutral Evil I believe (it's been a while since we played these), anyways, he's a crazy Cleric. He use to be a pirate.

And my Druid (Land-Mountain), name Wispy, is Chaotic Neutral and seems to be along for the ride, doesn't really have a purpose. Though he does have a cursed deer skull on that doesn't come off, and is always showing even when he transforms, so I can be like a rabbit with a deer skull helmet, a whale with a giant deer skull (it changes size according to my animal)

First one:
Anyways, one night, Brax and Wispy were walking around, and Brax sees a stable, he tells me to transform into a horse and wants to play a prank on the stable owner. I'm like, sure why not.

Later in the night, the stable owner is checking on the horses to feed, and my Wild Shape runs out. The owner sees me and I escape through the window. Brax sees me running and he goes to the stable owner saying that he needs to go, and would like his horse back.
The stable owner says, "I saw your weird horse turn into a man and run away." Which Brax then accuses him of selling his horse while he was away, calling the guards. He tells the owner, "Are you accusing me of giving you a fake horse?! I have had that horse for many years and he is a dear friend to me, I have never once ridden a man in my life! If you don't want the guards to come and jail you, you better pay up 10 gold." Got a nat 20 on intimidation or persuasion. Gave me 5 gold later because that's all I'm worth I guess.

Second:
Brax goes diving in a lake and finds an old boot or something, worth a few copper. We were at a shop for someone's quest and he's telling the shopkeep about how the boot is a rare item and is trying to sell it starting at 2 gold or something. Once again, he gets a good persuasion roll but the shopkeep is kinda skeptical.
Wispy walks in and admires the boot Brax is holding and I roll a good deception to convince the shopkeep it really is rare, and do a bid on it for 5 gold. Brax is totally in on it and tries to get the shopkeep to bid higher, which he does for 7g, then I just go, "Welp, I can't beat that," and walk away. The actual player gives me a look of like, extreme disappointment/betrayal, which is what broke me into laughter.

Third:
The 2 of us go to a woodcarver's shop, and he requests the shopkeep to sell a cat tower to him so I could lay on it. I turn into a cat and go along with it. Later we're at a bar/rave and he brings the tower with him and ends up getting so drunk he is using it as a boat to crowd surf.

4th:
Our group was doing a DBZ style tournament, where if anyone exits the ring, they lose. Our DM gave Brax a reverse gravity ball that he chucked at the enemy team, and used a wind spell to push them all off the stage.

5th:
Our party was going to fight a Red Dragon, I had a potion of flying and one more use of Wild Shape, Brax was our most reliable damage dealer, so I ended up drinking the flying potion, turned into a brown bear, Brax mounted me, and we charged into the Dragon's lair as a crazy cleric on a flying bear. He ended up getting feared but I was able to still get him closer. One of our party members died but we defeated the dragon.
The dragon turned into a small sentient lizard (had some magic on him that made it a crazy big dragon) that Wispy wanted to befriend. The "dragon" said no, so Wispy obliterated it with a lightning bolt

Edit:
And there's stuff other people in our party does.
Whole party 1:
In one of our first assignments, we had to raid a goblin filled cave, and we ended up kidnapping one of the goblins who we named Gary, we let him go eventually, but throughout the campaign, Gary has shown up as one of our plot points to help us out or to be used as bait of some sort.

We traumatized him so bad that he ended up killing some other goblins so we wouldn't hurt or kill him.

Whole Party 2:
Shorter one, we were walking through the forest when we encountered some giant toads, who kept eating our ranger, they didn't really do much else, so Wispy just sat in a tree and watched her struggle. She now has a fear of frogs.