Once in a DND 5E game on Reddit, a player's character, a clumsy wizard, tried to cast a simple spell to light a torch. But instead of the torch, he set his own robes on fire. It was hilarious as he ran around panicking while the other players just watched in shock and then burst out laughing.
There was a story where a rogue player on Reddit was trying to steal from a powerful mage. He thought he was being so sneaky, but he accidentally stepped on a magical rune that made his shoes sing every time he took a step. It was really funny as he tried to run away from the mage while his shoes were singing 'La - la - la' loudly.
In one of our adventures in Waterdeep for Dragon Heist, our group of adventurers got into a tavern brawl. The wizard accidentally cast a spell that made everyone's hair stand on end. We all looked like porcupines. It was so funny that even the angry tavern patrons couldn't help but laugh. And instead of fighting more, we all ended up having a drink together.
One funny DnD story from 4chan was about a player who tried to use a 'confusion' spell on a group of goblins. Instead of getting confused, the goblins started doing a chaotic dance and singing a made - up song. It was hilarious as the whole encounter turned into a comical performance rather than a fight.
Sure. There was a story about a guy who accidentally ordered 100 pizzas instead of 10. He had no idea what to do with all those pizzas, so he ended up giving them away to his neighbors and the local homeless shelter.
Sure. There was a story on Reddit about a guy who tried to train his cat to use the toilet. He set up all these elaborate contraptions and in the end, the cat just decided the bathtub was a better place to do its business. It was hilarious to read about his failed attempts and the cat's stubbornness.
In a DND campaign, a bard entered a tavern and challenged the local drunk to a singing duel. The drunk accepted, thinking it would be easy. But the bard started using all kinds of magical enhancements to his voice and performance. He made his voice echo like there were multiple bards singing, and he added illusions of dancing animals. The drunk was so flabbergasted that he passed out from shock, and the bard won the duel and free drinks for the whole night.
Sure. Once, my friend's character, a bumbling wizard, tried to cast a spell to make himself fly. Instead, he turned his robes into a giant, flapping bird that carried him around while he flailed helplessly. It was hilarious.
Once, a friend created a character who was a gnome bard. He was supposed to be a great singer but in his backstory, every time he sang, small animals would run away in terror. It made for some hilarious role - playing moments when he tried to perform in taverns.
One time in a DND game, our wizard cast a spell and rolled a nat one. Instead of hitting the enemy, the spell backfired and turned his own robes into a bright pink frilly mess. He was so embarrassed trying to fight while looking like a walking cotton candy.
In a DnD session, we had a paladin who was overly confident. He charged at a group of trolls, shouting heroic phrases. But he slipped on a banana peel (left by our rogue for some reason) and landed right in front of the trolls. They just stared at him for a moment before he scrambled up and we all burst out laughing.