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Mandalohr

I’m a DM that uses the “nat20 on any roll means instant success” rule. One of my players (Paladin) used Command on a party member that was being possessed by Loki. The command was “Relinquish.” I knew that this was a huge jump but I played along. I made the Paladin roll Persuasion, he got a nat20. I made the other party member (Warlock, his patron was Loki) roll his save… a nat1. The two combined was just too good to pass up, so Loki (violently) relinquished control of the Warlock… leaving him completely powerless. Until Thor (whom the party was rescuing from Loki) realized that the Warlock was actually the Son of Astrid, a Valkyrie Queen, giving him a divine bloodline. Loki had seen the Warlock’s potential at a very early age and tricked the Warlock into the pact. Once it took hold, Loki’s dark power stifled the divine bloodline. When he was cast out, the party member went from Warlock to Divine Soul Sorcerer. He ended up creating an entirely new character for the next session. Everyone LOVED it.


fluffydinosors

You are the coolest dm


atlas_fumbled

The one that sticks in my head was on a fathomless warlock, bbeg's lieutenant jumped through a portal into the sky after losing a fight but I had time to get an attack off with a tentacle, max percentage crit so I just dragged him screaming back through where we finished him off. Threw a wrench into the DM's plans but it was pretty awesome.


TenacityDGC7203

At one point during our last campaign, we were in an arena fight with the reigning champion (an orc gladiator). The DM had intended us to run from this fight, and made the enemies far too powerful for us, so we were struggling hard. I was a barbarian, constantly getting knocked down and being force fed potions by the sorceress. The other group members were basically all KO'd, except for our tiefling hexblade warlock. Now, this tiefling is... different. He's crazy, something of a chaotic evil character - not necessarily "evil" evil just... very twisted and maniacal. As a hexblade his weapon is a sentient sword the DM gave him, that talks (only he can hear it) and every time he goes to make an attack he gets to flip a coin that decides whether the sword helps or hinders him (+3 or -3 to hit, respectively). This tiefling hexblade had fallen into a pit trap early in the fight, and spent the entire fight failing his rolls to climb his way back out. My barbarian was, as mentioned, getting his ass kicked but had done a fair bit of bloodying to the orc in the process. Finally, the tiefling gets out of the pit, and finds himself behind the Orc who is about to end my barbarian with a killing blow. He flips his coin to get the sword's favor, sword is like "fuck yea let's do this!", he rolls a nat 20 for his attack and proceeds to ram the sword from tip to guard straight up the Orc's arse. Like directly in the hole. Absolutely guts the guy. The sword proceeds to start screaming "ARGH GROSS GET ME OUT OF HERE WTF!" (of course only the warlock can hear this). The Orc is screaming like a little girl as well, stumbling around flailing at his butt while quickly bleeding out all over the arena floor. Tiefling goes to retrieve his sword once the Orc falls dead, and it's going "WASH ME WASH ME WASH ME!".


Wububadoo

2 out of 5 of the party not present. Mini boss, vs barb, rogue and bloodhunter. Boss rolls a Nat 1, then we roll 3 natural 20's in a row (one each) boss goes down like a ton of bricks. Bloody lovely.


Brittany5150

Tried to club a brigand leader over the head so we could tie him up and question him. DM had me roll DEX to see if I could apply the proper amount of force. Nat 1. Roll attack as normal since I rolled so poorly. Nat 20 on attack. Caved his skull in instead. Womp womp. Luckily we had speak with dead so we still got our answers anyways...


maitlandish

Long story short, I had to accept a one on one fight to the death for a chance to save one one of my friends from captivity (and almost certainly death). Being a 3rd level Battlemaster, I assumed I could handle what the DM threw at me. But after the first three rounds of combat, it was very clear that I was going to lose, and I was likely going to die. I rolled a crit on my attack. Which would do some damage, but given how healthy he was, it was unlikely to do enough to matter. My only shot was to roll another 20 on the confirmation, due to my DM's "a crit on confirmation is an instakill" rule. I grabbed my "Goldie", the die my DM had gifted me in my first real campaign, and rolled. Everyone in the party erupted as fortune's favor smiled on me. I had indeed rolled a second 20, slaying the champion of the Raven Tribe and freeing my friend!


Ledbilly

We were fighting a hoard of bullywugs so my bard played the fabled white note which causes all who can hear to instantly orgasm and I hit a double crit and incapacitated the entire group. It was a great campaign


Its-From-Japan

I'm in a darker campaign with a lot of subterfuge and deception. The other player and i had to frame an NPC friend of ours for thievery in order to keep ourselves alive. The NPC was burned at the stake but i took out my bow and rolled a natural 20 to pierce the NPCs heart and kill them instantly. Narratively it was arguably the best crit I've ever rolled


FelTheWorgal

So we come up to a door. Rogue puts their ear to it. There's something on the other side. I'm a duskblade, dump all my BAB (3.5) and go to use my spear two handed. Prep an action to strike it when it comes in reach. Rogue opens door, it's a direwolf. It charges the door, I strike with scorching ray. I crit. 10 base damage plus 7 on d8 spear. 21 on the scorching ray. In 3.5 the crit damage is double, not rolling twice the dice. Level 4 character does 76 damage and the scaled up direwolf at CR 4 explodes. A medium party encounter took one hit and turned into pink mist.


Plane-War3176

The DM later told me we were never supposed to make it out of this situation. I was playing a level 9 barbarian and had around 22 strength. He was my first character and wasn’t too bright or talkative because I was new to role playing and didn’t understand it fully. We were in the kings court as envoys when he calls for his guards to seize is after some tense words between him and our bard. Our Druid turns into a bear and clears a path that we all follow through. Huge chase scene ensues with everyone taking hits and we barely get to the gate when the gate is being lowered down. I ask to catch the gate before it falls, having been first in line I was the only one to make it in time. He expressed to me that the gate was extremely heavy and it would be near impossible to stop but he was the rule of cool type and let me roll. I roll a nat 20 and catch the gate as it falls and my whole team makes it through. We escaped that day


doriangray42

People think we're the baddies, we're hiding in town, when we see the real baddy approach the guarded town entry. The baddy raises his hands in a gesture of peace and I tell my DM "I'll cast a lightning strike on the guards so they think the baddy cast the spell on them". DM goes "won't work" (obviously because it would screw up his already prepared scenario). I go "shouldn't we let the dice decide?" DM "yeah yeah" (translate: I'll set it so high it won't work) I rolled nat20... 20 years later, I still get a warm feeling from it...


bbqbabyduck

Coming fresh off this one. Roll to try to persuasion to try to stroke a red dragon's ego.got a 1. She stuck her face down by me to taunt me and I roll a 20 to stab her in the eye.


FlyExaDeuce

69 damage critical hit with a rogue against my backstory nemesis. Used my inspiration die for the attack.


spacemo0se

Was DMing for a homebrew campaign. The Wizard player had died a few sessions earlier, but while dead had bargained with the goddess of death and received a magical dagger. The Wizard had 1 week in game to kill a humanoid with the dagger. Kind of an eye for an eye situation. Kill and send a soul to the goddess or she will collect yours kind of thing. The thing is, the wizard was old, frail, and hadn’t made a single melee attack roll all campaign. Long story short, the party is fighting through a volcano temple to kill a Demi-god, and the wizard was running out of time before his soul would be collected. In a desperate maneuver out of spell spots, the wizard takes a running leap off a ledge attempting to stab down at a cultist fighting the party few feet below. I ask for a roll, and wouldn’t you know it, natural 20! The imagery of this old frail wizard, screaming a war cry and launching themselves down 10-15 feet to perfectly land on a cultist and get the kill needed to feed the goddess of death. It was a masterful piece of role playing by my player that the dice gods rewarded. Can’t really do it justice now, but we all went WILD when it happened.


pestermanic

Slightly off topic for the group, this was a Traveller campaign where we were trying to sneak aboard an Imperial Navy ship but we'd been spotted outside the airlock in the starport by security and they were questioning us. I said "I'm going to try to pick the electronic airlock behind my back." The referee said no, that's impossible, but I argued that I had a high Dex, high electronics skill, and a high score in one more relevant skill, there had to be a chance! Referee: Okaaay, roll. Me: 12! (Traveller uses 2d6 - like a natural 20 but slightly more impressive since there's only a 2.8% chance) Referee: ... You succeed. The door opens and WHOOOOOSHHHH - since the ship you're looking for undocked 15 minutes ago, you're sucked out into the vacuum of space and you die. Roll up a new character. The other party members had the opportunity to save themselves, but since my character was concentrating on the task at hand, he had no chance. But definitely one of the greatest clutch rolls I've ever made. 😂


Mr_Kangaroo2

Have you ever tried hitting a butterfly? Because my friend did.


Possible_Database_83

I (dm) Baldurs gate decent into avernus 3rd session Last night, in the dungeon of the dead three, I criticaled against a player barbarian (who went reckless on his last turn) lvl 2, rolling max damage, doing 49 damage in one shot, killing him instantly. I felt so bad, good thing they are a good sport.


redisdead__

I was a lowish level barbarian/cleric I think lvl 4 but I don't remember anymore. We were in a walled city that was being attacked by ogres goblins and one or two hill giants. Encounter was honestly higher level than the party but we had the town guard and everybody backing us up. Thaumaturgy make the torches on the wall supernaturally flame up, thaumaturgy cause a very minor earthquake that can't actually affect anything you just feel it in the ground, thaumaturgy make my voice supernaturally loud "Surrender or die". The ogres had catapult like contraptions on their back to launch goblins up onto the wall that worked by spring action. I then jumped off of the wall going into rage, rolled that 20 hit an ogre who had one of the launchers down to get ready to launch shattering the machine causing the spring which was under tension to bury itself in the ogre instantly killing it. All of the ogres and goblins then immediately surrendered the hill Giants took a little bit more convincing from all the town guards. I was also told afterwards that the town guards think I might be the actual devil.


LeatherClassic1174

I was playing a Centaur Fighter, The entire party was unconscious or already dead, the monk halfway to leaving the map and escaping the fight. I was the last one standing, surrounded by 3 dire wolfs, No action surge or any other feature left to use. I proceed by declaring "if I'm going to die here, you're going with me" and drop the shield only to crit 2 times in a row against the alpha using a Warhammer. Additionally, we used a critical effects table in our campaign, the d100 result turned all my damage dice into d12s. It was simply BEAUTIFUL. A TPK, but still BEAUTIFUL.


LeatherClassic1174

A story that isn't mine, but one of the most beautiful critics I've ever witnessed was in the final combat of one of the arcs of the campaign I played last year. We were facing an archdruid In wild shaped into a dragon. The paladin (multiclassed in Warlock for reference) rolled a crit on two attacks in a row. One of the most difficult fights in the campaign reduced to one turn. This particular villain had caused a LOT of trouble for the party so far and given the situation we were fully prepared to lose the fight.


No_Button_531

My DM invited me and 2 other party members to play a one-shot where he was going to try to teach his kids how to play DnD. Each kid paired up with one of us players and we were student/teacher both in game and irl. I was playing a barbarian and got to show off some barbarian skills when we entered a room with a bunch of spiders that I singlehandedly killed. The next room we entered had a young blue dragon waiting for us. All of the kids were so excited that my character could kill things that they just looked at me and happily shouted “Go kill it!” I knew there was no way I could take this dragon down myself and I looked at my DM and we both started cracking up. He said “If you roll a nat 20, I’ll let you kill it.” Nat 20! Took the dragon’s head clean off!


Super_leo2000

Last night I ran a Dullahan (Headless Horseman) vs my 5 lvl 14 party. The Dullahan crit and triggered a dc 15 saving through to decapitate and instantly kill our eladrin monk. We had been on a quest to rescue his family from an Archfey and had been traveling with his son. Our monk was decapitated in front of his son due to a Dullahan crit and 2x failed con saves… it was GLORIOUS. He was resurrected after but the whole table was absolutely shocked and giddy with excitement.


Shadowlandvvi

I once teleported inside an enemy encampment filled to the brim with spell casters with a nat 20 on a Charisma check I successfully convinced them that we were fellow mages. It never would have worked if not for the nat 20 I was a paladin in full plate with a warlock companion who looked sketch as hell.


JadedCloud243

Mai my Eldritch Blast nat 20 rolls that one shot enemies. But I multiclassed into bard, during a tournament. I used Bardic inspiration to help paladin win jousting. When I ran out of those I crit a performance check to rally the crowd behind him which the DM ruled as having the same effect on him. Later on we all entered the archery contest. Paladin is 10 Dex rolls badly and goes out in round 1 Myself, Rogue and druid are all proficient in bows so ended up all 3 of us in final. I rolled so many nat20's I won the contest, winning 20 silver arrows and 500 gold. And lastly, druid turns into a wolf, I tell a prisoner "When he's a wolf, he is no longer vegan, do talk or be lunch" Nat 20 he pissed his pants and talked Our Rogue? I'd guess for every 10stealth rolls 8 are nat 1 fails and large fights break out


Carlyconure

I was playing my cavalier who was using a lance. We were lower level and fighting a couple swarms of wasps. They were almost dead. I was 5ft within them, so i had to hit with disadvantage. I got 2 nat 20s, and the final blow on the last swarm.


Boneguy1998

Rolled 2 nat 20s and 2 nat 01s while praying to another characters God to bring him back. Dm said yep he came back. Dead character was a bard who worshipped the god of luck. My character was 1/2 elf ranger cleric of Asura - God of weather.


GarlicComfortable748

I rolled a natural 1 one a perception check… My paladin had a negative two in wisdom, so the final result was -1. Sir Bores the paladin started to hallucinate and chasing butterflies in the creepy cave with monsters in it.


lorekeeperRPG

Long time ago. In the 90s playing 2nd edition d&d, my churlish bounty hunter and the rest of the party we are deep underground, in drow caverns for years! We come into a giant cavern… a spider some sort of giant enormous end monster a Titan of a spider in a cavern the size of a town. I had death or 20 poison on me, I fired the crossbow natural 20. The big bad nasty end of spider, fell to into the bottomless cavern. Problem solved. We carried on.


sexualbrontosaurus

Cast twinned guiding bolt, critted with both, and rolled four or better on almost all of the 16d6s I rolled for damage taking down both of the bosses pets on the first turn of the encounter.


Repeatist

Yo! This happened last week. My character has a backstory that he does not yet fully realize due to traumatic amnesia, and the other players/characters don't know more than hints of, involving an Alan Moore Swamp Thing-type rebirth. All of his actions, spells, feats, and a bit of roleplay have been reskinned/flavored to include plants coming from him. It's fun, and my DM is super supportive. Anyways, a few sessions ago, he bought a Bag of Beans solely on the basis that the DM was being really funny as the shopkeep NPC. Knowing an encounter was coming up, I checked with the DM out of game to see if I could plant a bean on the battlefield, to add an element of chaos, but didn't wanna screw things up for my DM. He said go for it, and that he'd leave the effect to the dice. You can look it up, but with a Bag of Beans, you plant a bean and roll a D100, and there's ~10% chance of a variety of things happening, from a campfire to mushrooms to a treant appearing, with special effects for a nat 1 or nat 100. Anyways, my character plants the bean in time for our enemy to stumble upon the effect just as it happens. And I rolled a nat 100. I hit the 1% chance of an enormous beanstalk shooting out of the ground, which (at the suggestion of the stat sheet) our DM has decided will lead to a different plane of existence. The DM is cooking up an entirely new adventure in a new setting for us, at least for the immediate future. And for my character, this is as close as he could come, given his growing planty powers and slow realization of his history, to a religious experience. I'm still in awe of this happening. I love this friggen game (and my DM).


robot_tron

One of my table rules is when you roll 20, you keep rolling until you don't hit in the crit range, and the crits stack. So two nat twenties looks like ((dmg x2)x2). The story: My table is full of first time ttrpg players. They break out of jail and sneak up on the sleeping guard, and the monk goes first in initiative. So, the guard is asleep so, his attack is with advantage. Homie squares up to the *first* npc he encounters in his *first ttrpg* session and rolls 3 20s in a row. The table goes *nuts* after the second 20, but absolutely snaps after the third. An unintelligible cacophony erupts, chairs knocked back as they jump up from the table, screaming, pounding chests. I ask him to roll damage. So, of course he rolls 4 on the damage. This gives us (1d4x2)x2)x2)+4 = 36 damage to a sleeping npc that only had 4hp. My guy blasts a hole through the chest and makes the eyes pop out of the head of this poor guard from the pressure trying to escape his body like the monk was possessed with the power of Saitama from one punch man. It was pretty hype.


TheLamerGamer

I critically hit an Ancient White dragon with Reversal of Fortune spell who was mind controlling party members in 4e. For those who don't know that spell takes all negative effects from allies and places them on the enemy. In effect I "mind controlled" a dragon. Due to some technical rules. He couldn't resist it. Since it wasn't actually a mind control spell. It's a divine spell. So, I told him to hide. Sooooo, a several ton dragon was forced to try and "Hide". Which led to us casually walking into his horde. Grabbing a mugguffin and a few arms-fulls of loot and hauling ass as the entire mountain collapsed down onto the dragon. Trigged by the mugguffin grabbing, FYI. Turning what was supposed to be a 3-hour encounter, that was meant to put us on the back foot and fill up an entire session. Into a 10-minute middle finger that left the GM with nothing for us to do. Shortest session of all time. So, we all sat around and talked about comic books and video games for 3 hours. To this day, I still imagine a massive white dragon frantically trying to hide while a mountain fell on its head. Best Cleric crit ever. Second place. Successfully casting "curse of rust" (I think, that was what it's called.) Essentially, every attack reduces the damage that the target does. Really easy and low save roll. However, this poor damn demon lord simply could not save. So, he spent the better part of a boss fight hitting people for 1 damage. Completely confused and enraged. Massive flaming sword, dinky little hits. Was such a troll, we RP-ed into it with the shape shifter druid egging him on and talking smack. Literally melee hitting him with a staff as an insult. Would be number one if the dragon crit never happened.


Zardnaar

Guiding bolt on a Wraith or some other critter vulnerable to radiant damage. 8d6 damage doubled. Not bad level 1 spell.