Nat 1s leading to your best RP moments.

[Ventruenox]

So for some reason, the dice gods seem to present amazing RP moments for my group. The Bard of my group (the DMs wife) notoriously rolls poorly on her performance checks, which she roleplays as idealougue slam poetry. The kicker is that her current character is a SJW (social justice warrior) from an entitled background. I will admit that she can deliver well, but one might expect that from a player who has given a TED Talk. My character is partially a mash up of Foghorn Leghorn and Colonel Sanders, so I'm playing up all aspects of deep southern stereotypes.

At one point during our session last night, her character lost her temper on some Halfling children and she went full entitled whacko, going so far as to deliver racial slurs that you'd see in Clerks II. The Charisma check she rolled shortly after resulted in a nat 1. The NPCs physically attacked her in response to her (perceived) half-hearted apology. My character ended up having to man-splain consensual touch and "no means no" to the SJW. The irony was delicious.

My question to you all is how have you turned critical fail rolls into your best roles?

[zinycor]

My first character, on AD&D was a fighter, who because of his great constitution it was very improbable for him to fail saving throws... However, he failed, a whole lot of saving throws, on nearly every encounter... To this day I remember when facing an evil demigod, my character was the only one to fail the saving throw against a spell that made it so I would change sides... Then I tried to protect my new master.... by rolling a 1.... So... I eneded up killing the evil demigod by trying to protect him.

Good times.

[Chronos]

We were making our way through the Underdark, on the way to a Drow city where some crazy priestess was about to conduct a big nasty evil ritual. We find that there's a colony of stone giants on our route, and my rogue goes ahead to scout. He's got a great Stealth check, there's no chance the giants will spot him.

Well, unless he rolls a 1, and they roll really well.

So, they grab him and ask where he's going. And my rogue, being a very frank and open type, says "We're just passing through on the way to <name of Drow city>"
"What do you want with that accursed place!?"
"Well, hopefully to make it a little less accursed. See, there's this evil priestess named <whatever>, and we've found out that she's planning something called the Great Revenancing, and we're not entirely sure what that would entail, but it sounds like bad news for everyone, so we're hoping to stop her."

Meanwhile all of the rest of my party is cringing at me telling this giant everything, and wondering if I'm under some sort of magical compulsion to tell all, or something. But it turns out that those giants weren't a big fan of the Drow city, and just never had any opportunity to do anything about it, and they appreciated honesty, so not only did they not harm us, they escorted us past what would have been the next encounter.

What made it even funnier was that, right after that encounter I talked us out of with the simple truth, the next encounter we had after that, the bard managed to talk us out of with the most brazen bluff you've ever heard, aided by a really high Deception modifier and a natural 20.

[ProsecutorGodot]

Just yesterday my jerk Artificer tried to make fun of the party being stupider. I attempted to convince them that the exit to the maze that was clearly not the entrance we came in through was actually the same.

My natural 20 deception (mod if 0) was met by the Monk's natural 1 insight (+9)

Quantum Maze Gates are a thing now, we finally "escaped" by entering from the exit. The monk player was thrilled to play along.

[Samayu]

We rescued an elf woman. Or at least it seemed like we rescued her, but it wasn't clear. So then she tried to explain how she was the prisoner. Insight checks. One guy rolls really well. The DM was like, "her story sounds fishy." But another guy rolled a 1. And he was already predisposed to like her, due to her being an elf or something. So he totally went with it, and started actively defending her. At the same time found her, we liberated a stash of potions. When he learned that one of the was a potion of mind reading, he gulped it to prevent the rest of the team from violating her privacy by reading her thoughts. Finally combat started and he lost a round due to the shock of it. She almost wiped us.

[dragoeniex]

My bard is hot on the heels of a terrorist who's planted explosives beneath the town square. Being a traitor who came in with a special task force, the terrorist flashes some symbol to the royal gate guards and says something drowned out by the rioting crowds to gain access. I switch my glamoured armor to match his task force uniform while weaving between townspeople, then try to charge through with a curt "I'm with him." I've got a +13 to deception, and there's no time to bother with explanations as long as my spell-drained self can catch up to the guy with the kill switch. All I need is not to roll a--

Natural 1. Oh dear.

I make a dex check to get through but take four attacks of opportunity trying to catch the traitor. As I get close, voice cracking with desperation, the charges go off. My character is thrown into the air by the force of the explosion and breaks his leg landing. Compound fracture.

Suddenly, the suave and collected team face is offering advice on how to set his own leg (highest medicine score) between fainting spells. Due to the power of friendship, I have my broken leg splinted to our wizard's broom of flying. This leaves me hopping tiredly along on one leg with the other bent at its knee and hovering at standing height.

There is nothing quite like playing "good cop" during a terrorist interrogation when you've been run around, drained of power, blown up, and are watching torture efforts from your dumb, flying scooter. Intimidation and negotiation efforts just start trailing off into "...Listen, I'm tired, and neither of us are going to rest well with all your screaming. Just do us both a favor and answer the question. Please?"

Trying to float-hobble up the tavern stairs to bed afterward was practically its own encounter.

[LuccMa]

This story comes from a Birthright setting. The northern part of our kingdom was overrun by eternal winter, Kriesha, an evil godess of winter, expanded her influence and opened up a portal there. Our group was tasked to stop that. On the way there we encountered a mysterious woman - a priestess of Kriesha. She used some magic on my character and i resisted with an epic fail.
The journey continues and we learn more about why Kriesha is here: She tries to find her daughter who ran away. After more encounters with the priestess from before and two (!) more epic fails from my character, he ist very much convinced that Kriesha will just go away if we bring her her daughter back. Kriesha isnt that bad anyways. (In our setting she was, since the ancestors of my character banished her from this world)

We finally found the daughter, a big fight broke out - we, as the heroes, together with a small army from our kingdom vs. Krieshas frost monsters, coming out from a portal which led straight to her domain. My character picked up the daughter, jumped through the portal and gave her back like a good doggy. He also swore fealty to Kriesha - problem: My character was named "Hector". The Hound-like big guy with a sword and not that many words. Krieshas followers were all women.

1 Week later, Hector became Hectoria and left the group. I continued to play his junger sister and Hectoria became an antagonist for the campaign.

[Laserlight]

The party has been sent to find and retrieve another adventurer (new PC), and they meet him on a an abandoned gnomish ship trapped in ice. A few seconds later a couple of existing PCs and the new guy drop into the ship's hold, where they disturb something Very Bad. The cleric casts Banish and scrambles for the back of the ship, looking to find a way back topside. The new guy follows him. The third guy breaks a hole in the side of the ship, not realizing that he's in the hold and below the waterline.
The cleric, who is crawling (gnome-sized corridors) in pitch black darkness in the belly of an unfamiliar ship, feels cold water start running down the deck he's crawling on, and starts cursing in Deep Speech, because cussing in Common really doesn't do justice to the situation.
The new guy hears this. He just met these guys about 40 seconds ago, but almost all the talking during that 40 seconds has been done by the cleric, so the new guy has a chance to realize that the voice he's hearing is the cleric.
Or with a Nat1, perhaps not.
He unslings his rifle and fires. In pitch darkness, so the cleric is probably safe.
Or with a Nat20 and Nat20, perhaps not.

Years later, the cleric's player, when hit by friendly fire, is still likely to yell in disbelief: "You SHOT me!", and someone is likely to reply "You sounded like a mindflayer!"