I had a rogue in my party who rolled a Nat 1 on a lock - picking attempt. Not only did he fail to pick the lock, but the noise he made alerted the entire dungeon of guards. We had to fight our way out instead of sneaking through like we planned. It was a disaster at first, but it led to an epic battle that we still talk about. Nat 1s can really change the course of a DnD adventure in the most unexpected ways.
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.
One time in a DND game, I rolled a Nat 1 when trying to pick a lock. Instead of quietly unlocking the chest, my character ended up jamming the lock so badly that it set off a trap. There was a puff of smoke and a small explosion that singed my character's eyebrows. It was hilarious because it completely derailed our plan to sneakily loot the treasure.
There was a ranger who rolled a Nat 1 when shooting an arrow at a dragon. The arrow flew in the completely wrong direction and hit a friendly NPC who was trying to help us. It caused a bit of chaos as we had to quickly explain to the NPC that it was an accident. It was really funny but also a bit embarrassing.
During a DND campaign, my character rolled a Nat 1 for a stealth check. I was trying to sneak past a group of guards. Instead of being quiet, my character tripped over their own feet and made a huge racket. The guards immediately noticed and started chasing me. My friends' characters had to quickly come up with a plan to either fight the guards or create a distraction so I could get away. It was so funny because it was supposed to be a simple sneaking mission but turned into a chaotic chase scene all because of that Nat 1.
In a different RPG scenario, a fighter was in a duel against a powerful enemy. The odds were stacked against him. But then, he rolled a nat 20 for his attack. His sword strike was so powerful that it not only hit the enemy but also sent the enemy's weapon flying. This completely turned the tide of the battle and led to the fighter's victory. It was an amazing display of how a single nat 20 can change the whole course of a battle.
One of the best DND stories I've heard was about a party of adventurers who were tasked with saving a small village from a horde of undead. They had a paladin in the group who managed to turn many of the undead away, while the wizard cast powerful spells to hold the rest at bay. The rogue, being the sneaky one, found the necromancer controlling the undead and managed to steal the artifact that was powering the horde, thus saving the day.
One great DND GM story is about a GM who created a whole mystery around a missing magical artifact. The players had to search through an ancient forest filled with strange creatures. In the end, they found out that the artifact was hidden in a tree that was actually a disguised ancient wizard. It was a really cool twist that made the game exciting.
One great DND assassin story is about an assassin named Zephyr. He was hired to take out a corrupt noble. Zephyr infiltrated the noble's grand manor during a masquerade ball. He disguised himself as a servant and got close to the target. With a swift and silent strike of his poisoned dagger, he completed his mission and vanished into the night without a trace.
One great grapple story was when our barbarian tried to grapple a giant spider. The spider was huge and the barbarian had to use all his strength. He managed to get a hold of one of the spider's legs and then started swinging it around, causing chaos among the other smaller spiders in the area. It was both hilarious and a strategic move that helped the party gain an upper hand in the battle.
Sure. A ranger was trying to track a rare beast. With a nat 1 on the tracking roll, he ended up leading the party in the completely wrong direction and into a nest of much more dangerous creatures. It was chaos as they had to fight their way out, all because of that one bad roll.