I remember a bard in our party who was supposed to sing a song to calm a group of angry goblins. But he forgot the lyrics and started making up the most absurd words. The goblins were so confused that they just sat there scratching their heads. It was a great comical relief during a tense moment. And we all still laugh about it when we recall that session.
My group had a paladin who was always so serious. One time, he had to cross a rickety bridge. He was being all cautious and noble, but then a squirrel ran across the bridge and he freaked out, thinking it was some kind of magical beast. He ended up falling into the river below. His pride was a bit hurt but the rest of us couldn't stop laughing.
There was this time when our rogue tried to pickpocket a noble. He thought he was being so stealthy, but he actually grabbed the noble's pet mouse instead of his purse. The mouse started squeaking and running all over the noble's clothes. The noble was freaking out, and we were all trying hard not to laugh. Our rogue was so embarrassed.
One time, a character in our game was so scared that he ran into a wall instead of away from the approaching horror. It was hilarious to see the player's face when they realized what their character had done. It was like a cartoon moment in the middle of this spooky game.
A paladin I knew in a DND session tried to use his holy powers to bless a barrel of ale. He thought it would make it a 'holy ale' that would give extra strength to those who drank it. Instead, the barrel exploded, drenching everyone nearby in ale. It was quite the mess and everyone was laughing at his miscalculation.
I had a really funny moment when I was trying to rob a stagecoach. I jumped on it all confident, but then I accidentally fell off the other side. My character landed in a bush and got all tangled up. The driver just whipped the horses and drove away while I was struggling to get out of the bush.
During a mission in Waterdeep for Dragon Heist, our cleric was supposed to heal a sick person. But instead, he misread the spell and made the person's nose grow really long, like Pinocchio. It caused chaos in the town square as everyone was trying to figure out what happened. We had to run away from the angry mob while still laughing at the cleric's mistake.
One funny story is about an engineer who was presenting a new software design. He was so excited and talking really fast. In the middle of his presentation, he accidentally clicked on a wrong button and a cat video started playing on the big screen. Everyone burst out laughing.
I heard of a nursing teacher who was demonstrating the use of a wheelchair. She sat in it and was supposed to show how to move around, but she accidentally rolled right into a stack of textbooks. It was really funny.
A friend of mine was at a water park. She went on a really fast water slide. When she came out at the bottom, her bikini top had twisted in a very strange way that made her boobs look all wonky. It was super funny. She had to quickly adjust it while we all laughed.
In one DND session, a druid decided to turn into an eagle to scout ahead. But he misjudged his flight path and ended up crashing into a tree. He then transformed back into his normal form, dazed and with leaves in his hair. His party couldn't stop laughing as he tried to explain how the 'evil tree attacked him'. This simple mistake made for a really humorous moment.
There was a game where a group of players formed a secret alliance. They were so secretive about it that they accidentally started attacking each other instead of their real enemies. It was a total mess and really funny to watch as they scrambled to figure out what went wrong. Their expressions of confusion were priceless. This moment made the whole game very entertaining.