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.
Once, my character, a clumsy wizard, was trying to cast a simple light spell in a dark dungeon. Instead of just a small orb of light, he made a huge explosion of blinding light that not only illuminated the whole area but also scared the rats so much they ran right into the goblin guards, causing total chaos.
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.
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.
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.
One funny paladin DND story is about a paladin who was so dedicated to his code of honor that he accidentally challenged a very old and cranky tree spirit to a duel. The tree spirit was just sitting there, minding its own business, but the paladin misinterpreted some rustling of the leaves as a threat. The duel consisted of the paladin trying to swing his sword at the branches while the tree spirit just dropped acorns on his head. It was hilarious to see the paladin getting so frustrated.
Once, our party's bard tried to charm a dragon with his music. He started playing this really wild tune. The dragon just looked at him like he was crazy for a moment, then started to sway along as if it was enjoying the show. It was hilarious seeing this huge, terrifying dragon getting into the music instead of attacking us right away.
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.
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.
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.