What are your funniest Nat 20 moments? #9

[@marcusfabela3024]

Who else gets so sad when the outro appears. I’m like “aww it’s over? I wish these videos were longer

[@Bentron88]

I agree. So let’s submit as many as possible

[@aiodensghost8645]

Always. Which is why mega videos are the best

[@BrianVaughnVA]

We've got a long video coming soon about descriptiveness. Ripper is worried it won't do well, but if yall love it - we'll get more.

[@funnyplanet6787]

​@@BrianVaughnVAit's Brian Vaughn VA!!!!

[@BrianVaughnVA]

@@funnyplanet6787 It's me! It's you! We love you!! FP6787 I hope you have a wonderful December and please, make sure to keep hydrated!

[@TheSimbaman]

One of my friends ran a one shot of our group being kolbalts looking for a new home for our tribe. We rolled a world event in which we found a group of high level adventures. Our DM flat out told us that if this goes bad, this is a TPK. I was playing a barbarian, and with a little investigation we found out they were the cause of us losing our home fighting a storm elemental. The adventuring group looked at us and said we are sorry for your loss and I said “ it’s ok we F### like rabbits.” my DM told me to roll, nat 20 they laugh, and give us some gold for our troubles. My group is laughing their ass off.

[@Starfloofle]

Honestly that's hysterically in character for kobolds, that deserves an inspiration LOL

[@conspiracypanda1200]

My sister has been playing a game and telling me about it. Every session her cleric gets traumatised in some way. Her friends are burned alive, her tribe is eaten, her favorite NPCs get slaughtered, her own party members that she gets close to end up torn apart - for one reason or another everyone she cares about ends up dead in front of her! It started out as just plot to motivate her, but most of it just came down to bad luck and worse rolls. Early in the campaign, sis and her party adopted two dragon hatchlings. One of them, the female of the pair, bonds with sis. Basically, this dragon is like her daughter. Sadly, they have to send them away to another plane to grow up in safety, after which the dragons returned occasionally in adult human forms. One session, however, the party goes to an event that at the very end involves picking one of two boxes. One of the PCs picks a box and the other dissapears. Under the box is... The male of the two dragons they'd adopted. And the leader of the event wants the party to "sacrifice the dragon for the finale". This ends up with a big fight and the dragon dying. Thankfully, with sis being a cleric she is able to revive him and they escape. She then asks him if his sister, the one who bonded with my sis after hatching, was in the other box. The dragon confirms it and my sis realises her character is going to lose yet another loved one. So she prays really, _really_ hard to her deity. Nat 20. Her god decends down in a shower of light with the female dragon in her arms. The god hugs my sis' character while she cries and thanks them, then kisses her softly on the head. The god claims she has suffered more than any other, comforts her over her losses, commends her on her bravery, blesses her, and leaves so that the party and their dragons may recover. Two sessions later sis adopted an imp friend and an hour later it was one-shot in front of her via an arrow through the skull. So... back to the usual, I guess. Edit: She rolled a successful divine intervention before turn one of the semi-final boss fight even started (it was against an elder brain dragon) and her god kamikaze'd herself to kill it in one hit. Sis had to reclass for the next (final) session.

[@CoffeeBnuuy]

That cleric is gonna need a therapist by the end Jesus christ

[@mackenzierinier4956]

Our group was sent into a town. The entire town knew who we were and the loaner who lost his wife somehow has a wife. It was like we we somehow been living here all our lives. We had jobs and families that were curious why we were acting strange. Turns out it was a bunch of blood golems and we were under an illusion spell. We had to eat a mushroom to counteract the spell. The one player was refusing to eat the mushroom. He didn't want to loose his entire family again. I screamed "eat the f***ing mushroom!" Then rolled a nat 20 to shove the mushroom down his throat. Once he swallows the baby who he had been holding turns into some kind of worm made of blood. We still shout eat the mushroom when someone doesn't want to follow the group.

[@TopaT0pa]

imagine waking up from that illusion and holding that abberation. Phew...

[@kevvillanueva2660]

Holy crap that’s gotta be so emotionally brutal

[@ETREDROOMREVIEWS]

The DM and players in that last game are clearly fans of One Piece with that last story. "Just an injured old man."

[@ankh-es8os]

One peice? Isn't that the new Netflix show?

[@izuku3111]

@@ankh-es8os no its an incredible work of art

[@aiodensghost8645]

​@@ankh-es8osthe anime is over 1,000 episodes long. I'd be dead before I ever finished it.

[@GTdba]

The player shushing a zombie back to his grave happened to our party as well...except it happened with our Goliath Bard, El Caldero. He simply punched the lid of the coffin and pushed back the skeleton inside, stating " No! Malo Esqueleto, MALO!!!"

[@SomeRandomKydd]

My brother once rolled a 20,20,2 to kill a spider and it exploded. DM had us all roll Dex, which we failed, to avoid getting spider rights in our mouths. Then he did the same with the last of the skeletons we later encountered, then Nat 20ed the black dragon with a Sword of Dragon Slaying. For story reasons the dragon left rather than die, but my dad said there was more Nat 20s that session than in his whole prior career.

[@attemptedunkindness3632]

High lvl game where we knew the king was going to be kidnapped and hostaged but didn't know when so sorcerer disguised as king would be the bait and we could spring the trap on the trap but first _we had to kidnap the king first_ allinall, a good plan. I was fighter and was expected to grab king from bed chambers and he resisted so I say "I am going to strike him in the head with the blunt edge of my blade to knock him out" I rolled a 20, then another 20.... I had a vorpal sword. We couldn't disobey the dice gods will, the king's head spun off his shoulders and fountain of blood shot up. We ended that session as wanted criminals, but fake king sorcerer was already sitting on the throne when this went down so we got away next session. We don't return there.

[@darioschottlender]

On my first ever D&D game I was some sort of warrior (I don't remember which mostly because at the time I didn't know about classes or whatever that much) and we were in a pretty laberintic dark dungeon, we didn't have a way to see. So I went in touching the walls to follow something, always the left side to not get lost and thought my party was following me; but it turned out that they got lost and I was alone. When I got into a room, suddenly torches went on and I found myself surrounded by 8 goblins (which I thought it was a death sentence if I would fight them). I decided to roll for intimidate, DM asked me "what do you do?", I said I swing my axe left and right while screaming... Ovbiously... Nat 20; DM makes 2 secret rolls. So he told me "You close your eyes and start swinging your axe left and right with such luck that the end of your axe hits one of the goblins and kills it instantly; the other seven run away in fear". I know it wasn't a super wow moment but I was so proud to having a moment like that in my first ever game lol, that did give me a confidence boost.

[@Neme331]

“Not like that! get away from my pants.”💀

[@DasPingvin]

One of the absolute best Nat 20 moments I have ever witnessed was as a DM for a group playing Descent into Avernus. The group had just had a fairly simple encounter vs a flameskull that had a golden crown with jewels inbedded in it and after the encounter the new druid said "It'll take to long to remove the crown out here, so I'll bring it back with us!" and puts it in his backpack unaware of the fact that a flameskull regenerates to full strength after an hour. So after an hour of sneaking back towards High Hall in Elturel a laughter emits from the druids backpack as it casts Fireball inside of the backpack, everyone has to roll Dex Saving throw and I have the Gnome Druid roll it with disadvantage due to wearing the backpack and he rolls a double Nat 20 and he describes it as "When i start to feel heat emitting from the backpack I toss it into the air and throws myself on the ground". We will never forget that session!

[@weebfanfics5454]

The last one is definitely the best

[@FuryJack07]

2:24 considering it's what she used when she didn't know what to do, I would've called it "Plan A, B and C"

[@Xarestrill]

This is kind of silly, but you asked for more Tame ways to shut down an encounter. Way back in high school in a 2e campaign, I was playing a Thri-Kreen who wasn't the brightest character. He was in a large town at the tavern. Suddenly hears banging on the door, so goes over and answers it to see who's there. Turns out it's a horde of about 30 zombies. I just said "Sorry, we're full" and closed the door. Several seconds of silence with the DM having an very confused look on his face

[@aiodensghost8645]

This is a "DM.exe has crashed" situation

[@Starfloofle]

Thri-kreens are those praying mantis looking dudes right? Somehow that makes this entire scenario all the sillier LOL

[@techicolorslowpoke2702]

First ever campaign i did. i was a Folk Hero Silver Dragonborn Paladin. We were in this crypt, and i suspect there might be a trap down the way. I find a boulder slightly bigger than a bowling ball, and roll to "roll it down the hallway to check for traps". Got a nat 20. There were no traps, but a homeless man was sleeping in the crypt, and my nat 20 bowling (granny shot style) had crushed this man's legs like an empty toothpaste tube. everyone was laughing their asses off, but i was just like "I SWEAR IT WAS AN ACCIDENT" and my paladin was violently sobbing

[@WytheA]

My best nat 20 moment waa the first encounter of our campaign. My character was walking through a dining room, when a chair mimic attacked me. My DM had me make a dex saving throw to see if I was grappled or not. Nat 20. And I had a +5 for the saving throw. 25 in total. My character dodge-rolled to the side before that mimic could even touch me.

[@karisasani7006]

It wouldve been better tbh if that big a saving throw meant you instead were the one who grappled the mimic

[@centric3125]

​@@karisasani7006 following up, he counters by throwing the chair mimic against a wall.

[@albinoreaper2949]

So, when my party began our first campaign, our DM asked us all to roll two D20’s to decide on what artifact of what element we would get to have, the closer to 20 obviously being how strong it’d be. I bet the DM that if I didn’t roll two 19’s or higher, my character would wear only a loincloth the first five sessions. She accepted thinking RNG would kick my ass. Two D20’s later, everyone is laughing their asses off and I have a flaming zweihander that can destroy souls.

[@lotsaspaghetticodejr.6488]

I was a Human Monk struggling with alcoholism. Pathfinder. I took the Alcoholic flaw, meaning I'd have to make a Will (Wisdom) Save in the presence of alcohol to resist drinking it. I also took a few levels of Rogue for Sneak Attack because in Pathfinder there is a way to get Sneak Attack damage dice on unarmed strikes, during Flurry of Blows and it is just hysterically over powered. Session Zero where we all meet up. Everyone at the table is meeting up in the tavern and talking. Everyone, except me. I know, a drunk not in a bar? Whaaaat? They leave and the DM says they find a disheveled man passed out on the outskirts of town wreaking of alcohol and piss next to a bonfire. One kicks my leg and I wake up. DM: Okay go ahead and introduce your-- I SEARCH MY BACKPACK you uuh, find your belongings? Nooo, I want to roll to search. I'm a drunk and a thief. I want to know if I stole anything or lost anything. Okay okay fine roll. Nat 20. The very first roll of the game. Nat, fucking, twenty. DM let's out an annoyed sigh, flips through the pages of the book and says I stole an Everburning Torch that (house rules) can be used as a +1 mace (1d4 bludgeoning + 1d4 fire) ((normal rules, EBT is magical, non-harmful fire)) And that, my dear friends, is how my alcoholic kleptomaniac Drunken Monk / Thief build got banned from ever searching his own belongings again ahahahaha

[@earthbit.]

Man, I was JUST thinking I could use a good “rolled a 20” video to loosen up after work. Perfect timing. Probably used up all my luck for the week.

[@aiodensghost8645]

Take some of my luck... I have plenty to go around

[@biggiouschinnus7489]

My favourite nat 20 moment was with my high elf rogue. Our party - me the posh rogue, a creepy Slavic grunge druid, and a 2000s pop bard - are drinking in a tavern where all the npcs are halfling children. Eventually we learn that the there have been creepy sounds coming from the tavern basement. I decided to make a dramatic appearance by materialising from the shadows, and our DM (who loves this stuff), has me roll for performance. Nat 20. To visualise, my High Elf rogue was 6 ft 5, wiry, and wore a leather mask with green eye lenses, in addition to a full traveller's hood and cloak over a blood red tunic. And this guy just melts out of the shadows without so much as a whisper or a creaking floorboard. Shadows follow in his wake, his black hair seems to swallow light, and he doesn’t walk into the room so much as glide. The children are so awestruck by his dark majesty that they forget to even panic. Turned out that a demon had put all the adults of the town into an unnatural slumber, and we spent the rest of the session chasing down cute little animate bells that were needed to exorcise it.

[@theojarrett4155]

One of my favorite nat 20's was pretty recently. My character is a wild magic sorcerer kobold named Korki who has a chameleon familiar named Pascal, and he loves to play the bagpipes (which two of the party members swore was a horrid instrument). So, we were in the shadowfell to infiltrate some evil lady's castle to steal the macguffin when we came across some locals who were being held against their will as workers. The rest of the party hid while the warlock started to try and gain the trust of the local and I said that I wanted to start playing soothing bagpipe music from my hiding spot of a hay bale to attempt to comfort the captive local. As if out of spite to the now groaning fellow party members I rolled a nat 20 + 9 and the local was completely calmed down which allowed us to get a lot of information from him. We then promptly ignored a large amount of the info he gave and for some reason everyone thought the best way to get in the castle was to just walk in... power word kill is a nasty spell... R.I.P. the fighter

[@dwaynejackson551]

The best Nat 20 isn't mine but my brother's. He was playing a monk and asked for a plate at the very beginning of the campaign. He kept this plate until near the end of the adventure. As the BBEG ran off he throws this plate under the fleeing guys foot and trips him up and he falls so hard he shits himself. I, as the DM, rolled for damage from the fall and a constitution check because the rogue managed to poison the BBEG which was why he shit himself.

[@gengarzilla1685]

Well that's a Chekhov's Gun moment if ever saw one.

[@docwil2541]

I'm an old-school DM from the 70's and consider myself a storyteller, and the players are the heroes or villains in that story. The dice, they are the will of fate. Recently my 20 year old son was playing a 4th level Goliath Barbarian in my low-level campaign. When a war party of 6 goblins ambushed and killed the human farmers, they were trailing. He charged the 100 yard ahead of the party while the goblins were stripping their kill. He arrived just as the goblins looked up.... roll initiative, he goes first. He grabs the biggest goblin by the neck and rages (Nat 20).... Then smiling reminds me he just increased from Med to Large. I didn't even have him roll damage. I just ruled that he snapped the War Captain's neck as he reverse hung him. Morale check as one goblin nopes right on out. Next round initiative, son comes in about mid way. One goblin makes a brave attack with a spear... (15) , my son smiles again.... Stones Endurance. He turns toward the attacking goblin with the only weapon he has in hand (the War Captain), both hands around the neck he swings .... and he rolls another Nat 20, right in front of me. (it's going to be one of those nights). I'm like, yeah, the rest of the goblins, nope out and run into the forest. He spends the rest of his rage trying to impale goblins on tree limbs with the rest of the party, maintaining a very respectful distance.

[@phillosopherguitarist2673]

I've been sooo impatient for this!

[@Jessie_Helms]

In my homebrew world Naturverden, I decided when I’m determining gold if I roll max (nat20, a 6 on a d6, etc…) that means I’ll roll again. Veridia, a noble background Druid who’d been working at this fancy cigar house for most of the Tenday, invited the rest of the party to work there for their last day or work before their caravan was ready to move out. Shopping montage for getting fancy enough clothes and all. Well, Manasa, who’s been rolling horribly on all of their charisma based checks all campaign, and who we all joked would probably only get pity tips…. I rolled a _58_ Nat20, nat20, 18. Meanwhile Veridia got like 15 gold. “So seeing how utterly out of your depth you were, every single coworker individually decided to slip you a portion of their tips for the night- you were only _given_ like 5 gold in tips, but ended up with 58 by the end of the night.”

[@postapocalypticnewsradio]

PANR has tuned in.

[@swagathan5]

Hello there!

[@Arelenedhel]

This is exactly what I needed today. Thank you for bringing a smile to my face.

[@darioschottlender]

9:14 That was the best "drops mic" moment I've ever seen lol

[@NexeL_NKC]

It wasn’t a nat 20, but was a critical success if it still counts. My character had been taken down by a flesh golem, and I was rolling death saves. The drunk monk of the party saw I was down, then threw a health potion, INTO MY MOUTH. Monk: **throws potion**. The bottle: **thunk**. Me: **wakes up in hysterics due to to the incredible throw of the monk.**

[@oogiedaoctopus774]

Once I rolled nat 20s back to back in real life once. I was on youtube and I got recommended a MrRipper video! But then after I clicked on the video it started with "Hey everybody, Brian Von Via here back at it again..."! Truly work of the dice gods above.

[@xamoel3884]

For context we were at the begining of a session, at the final battle, Me : can i, befriend it? Dm : sigh, alright roll for persuasion Me : 20 Dm : it stops directing its murderous intent towards you but is now convinced that everyone else are trying to kill you, his friend and goes into a rage. Next turn Me : can i seduce it? Dm : seriously? Fine you know what i'll allow it if it's a 20 Me : nat 20 Long story short, the dm hates me because apparently seducing the last boss and ruinning a session isn't funny

[@Mr_GoR_]

Ok, so, this is kind of dumb... running ToA (no spoilers); Party is finishing up combat in one of the rooms in the dungeon, one player uses a ranged spell attack against a creature that had been exchanging melee attacks with another PC and shouts, in character, "KS!" [kill steal] before rolling. Nat 20. The NPC wizard that had been accompanying the group sees how this "chant" greatly improved the result of their attack and on his turn does the same, shouting "Kei'ess!" as they use firebolt -NAT20! So now this wizard believes "Kei'ess" is a secret word of power that increases the accuracy/potency of spell attacks.

[@frankyquilavafireblast895]

It’s been a hot minute since I’ve watched any of the longform videos. I always keep forgetting how much of Brian‘s warlock voice kills me every time he does it.

[@peripheraldevotee94]

I was running a speedrun version of Curse of Strahd for one of my groups while our regular DM was on holiday in America, and the group were up against the last druid in the Wizard of Wines they found (by the basement door). The open-hand monk of the party was the only one who rolled higher in the initiative than the druid, and he rolled three nat 20s with each of his attacks and wiped him. I was using gummy bears for miniatures and threw that one at him after that poor druid got piledriven through the stairs into the hard ground.

[@Enigma1788]

In one of the first campaigns I took part in as a player, we had a party that consisted of myself (a fighter), a ranger, and a rogue. Our group was tasked with finding bandits hiding out in the mountains. We eventually managed to find their hideout and came across three guards that were spread out and watching the entrance of a cave. Not wanting to raise an alarm, the rogue and myself moved on ahead in stealth to try and take out two of the three guards while the ranger held back and prepared to fire at the third. The plan was to take out the guards all at once as there was just enough distance between them to potentially sound an alarm if we couldn't take them all out at the same time. Anyway, the rogue gets near their target, the ranger is ready to fire at the second target, and I'm ready to dash in and slaughter the third. At that moment, the rogue critically fails their stealth roll. The ranger attacks and takes out the second target in one hit and needs to focus on saving the rogue. Meanwhile, my own target is alerted and running towards the cave. Not knowing any better, I do the only thing I can think of: Me: I want to throw my greatsword at the bandit! My two party members just give me this look that says "You can't be serious!" Once the DM stops laughing, he says: DM: Sure, I'll allow it! He's only about 25 yards away, but I want you to roll at disadvantage since this isn't something your weapon is designed for. Roll two d20s and use the lower roll as your chance to hit. Then the famous last words: DM: Just don't go into this expecting to actually hit the ban..... Me: Two 20s. That means I hit him, right? At this point, my two other buddies playing the ranger and rogue are completely losing it and unable to breathe with all the laughing they are doing. Meanwhile, the DM is just completely dumbfounded that against all odds, the dice willed this completely ridiculous idea into being. DM: That's...*sigh*...just roll your damage. 4d6 plus your +3 strength modifier. In hindsight, I believe my friend that was acting as the DM was silently praying that I rolled low enough to wound the bandit, but not kill the bandit. I roll the four dice and come up with 23 once everything is added up. My friends are howling, the DM is just staring at my damage roll, and after a moment I realize the damage I did is far more than the arrow that killed the first bandit. Me (unintentionally metagaming): I assume that a 23 kills the bandit? John killed his bandit with far less damage. DM (still absolutely dumbfounded): Yep, this is really happening. DM (now narrating): "The greatsword gracefully spins through the air before landing dead center into the back of the skull of the bandit and embeds itself up to the hilt of the weapon. The bandit stops dead in his tracks, stands for a moment, then slowly falls forward, but the body stops at about a 45 degree angle as your sword manages to perfectly balance itself onto its tip following a one in a million shot that will NEVER. HAPPEN. AGAIN!" For the record, I did try to prove the DM wrong on that last bit in a future session only to have the dice extract their revenge as a natural 1 ensured my sword got embedded into a wall the next time I attempted my nonsense. The dice giveth, and the dice taketh.

[@maxblake5564]

I’ve got a great one. Our party was saving a bunch of Kenku from being bred as slave labor in a warehouse when one character, our yuan-ti murderhobo motherf*cker jackass druid, decided to set the warehouse on fire. Why? I still don’t know. We managed to get all the Kenku out safely somehow, and were just about to leave when two smoldering bugbears popped out of two smoldering crates. We roll initiative, and my character, a CN Tiefling School of Necromancy wizard, went first. My character raised his finger, pointed at the druid, and shouted at the top of his lungs “HE DID IT! HE DID IT!” DM had me roll Persuasion. I rolled, saw the result, and screamed almost as loudly “OH MY GOD! NAT 20!” After hysterical laughter on everyone’s part (except the druid’s) the DM said that the bugbears immediately charged straight at the druid, and kept attacking even though the druid tried to heal them. I did not take part in the battle and ran away as the authorities approached to ascertain WHY THE HELL THE WAREHOUSE WAS ON FIRE. Side note: because of this encounter and a few other things, our half-drow GOOLock called my character “the master of the perfectly timed Nat 20.”

[@Placidusax-101]

"Not like that get away from my pants!"

[@emberthecatgirl8796]

I was playing Lancer (mech sci fi). What happened was that we were falling towards a planet in an escape pod. The DM says “the escape pod is second hand, so I’m rolling D100 to see how smooth the landing is”. We rolled nat 100. Needless to say not only did we barely feel the touchdown, but we evaded enemy radar AND got a free repair. When we disembarked, we found two enemy mechs crushed underneath and a perfectly cooked goose stuck on an antenna.

[@madmalkavian3857]

DM was very determined to have this character outrun me but luck decided that shit wasn't happening as I rolled 5 nat 20s in a row. Literally each time was asked roll to keep up and so my musketeer looking ass was just relentlessly chasing this person trying to escape.

[@SoraPierce]

Had a Nat 20 for a one shot where i was playing a Minotaur fighter. My two sorcerers were trying to convince the final boss and his lizardfolk underlings that we were entertainers sent by the city. DM has us roll performance checks for dancing cause our guy sorcerer had like ghosts and a ghost dancing to save me from ignoring a stealth check like a minute prior. Our girl sorcerer, she rolls a 8. Hes unimpressed. My minotaur fighter rolls a 20. Everyone including the DM started cracking up at the idea of this nearly 7ft tall minotaur dropping his greataxe and proceeding to drop it low for the homies. Boss laughs so hard he believes us to be a comedy group. We then proceed to nearly escape, forget the hostage then i rolled a dirty 20 to "kool aid man" break through the keep wall to rescue the hostage without starting the encounter. Threw her on my back then we just went running. It was the DMs first time running a dnd thing and he got the circus ending.

[@saychaysarchive7065]

We're doing some one on one mini sessions to cover an in universe timeskip in our Transformers TTRPG campaign in a post-war Cybertron. My player is solving a murder mystery and tracks the killer to where the Seekers live (Seekers all look like Starscream but are different colors). He was interrogation Sunstorm whilst I had the music bot play Ace Attorney music (Orange Starscream) and he had caught Sunstorm in a lie and rolled to press him on it. He rolled the big two-zero, so I put the Pursuit them on and Sunstorm came clean totally, had a breakdown, and even revealed he had an accomplice.

[@luigines6457]

Had a couple of funny Nat 20 moments in a game I'm in. First one was when we were talking to the Mayor of Phandalin in the Mines of Phandelver campaign, and he was being stubborn and not giving information. The first time we met him, we had captured some bandits and put them in the prison in the town hall. I tried to speak with the bandits to get some information. They mocked me, and I attacked one, and rolled a 19. I then intimidated the mayor to see if I could get some information from him instead. I was allowed to roll at advantage, and succeeded. After going into the hideout, we came back to the mayor, and he hated me, but frustrated at how little he was giving us some trouble, so I rolled for intimidation again, and rolled a Nat 20. He gave us what we wanted after that. The next funny story in the campaign was after we went to a tavern to have some fun, and my brother, who is a Rogue, rolled to steal my poison set I had, and rolled a 19. Just as he was writing it down that he stole it, I said I rolled to try and steal it back. Nat 20. He was paranoid that I poisoned his drink, he refused to drink at all that night (I didn't poison his drink, but I let him believe it). Last funny story isn't mine, but my friend's. He's a Barbarian, and when we were in Cragmore Castle, he went into a rage before charging into a room. He asked if he could break the door down before entering. He rolled a Nat 20 on a strength check and sent the door flying into the other end of the room and knocked over a Goblin that was in the line of fire, and was left at 1 HP, before charging up to it and finishing it off.

[@sunfurycommenting1013]

Two stories of mine; During my second D&D session ever, our party faced some troglodytes (pretty sure I misspelled that) and finished them off. We later stumbled upon their lair, a foul cave of horrid odor and abhorrent fluids amidst the garbage piled within. Even my character, a gold dragonborn fighter who loved to collect knickknacks and shinies, refused to even search for anything because of how disgusting the place was. The half-orc wizard, however, decided that the best way to deal with the place was to burn it. My character and our half-elf ranger disagreed, but the human paladin supported it, so we didn't try to stop him. Unbeknownst to all of us, our DM rolled for flammability. Nat 20. The monsters den flat out explodes, acrid and sickening smoke billowing out into the tunnel (we were underground) and the paladin failed a constitution check and began hurling from the stench. Our half-orc friend nearly died, and forever after has a wretched smell lingering around him, tainting all that he touched with its vile nature. Second story; Same party as before. We were looking for a way out of a cave system and came upon a fork in the tunnel. The ranger and I scouted ahead since we were the stealthiest, and we had heard there was a cat like beast around. I ended up choosing the catty path, and nearly ran right into its sleeping body. It rolled a Nat 1 on perception, lower than my 4 upon approach, and because my character Lhachiel felt killing it in its sleep was wrong, she snuck back out. The party then proceeded since we needed to get past the cat, and wouldn't you know it? It rolled another Nat 1 perception. Lhachiel wanted to leave it be but then someone shot it. It rolled low again for its attack, and did next to no damage as we brutally murdered it, Lhachiel crying, "I'm sorry!" as she slashed its nose. It died pitifully and we found out that it was half blind, deaf and old (DM's way of explaining how it failed its rolls so miserably) and Lhachiel vowed that if we ever found another ice cat, she will refuse to fight it. Meanwhile the wizard wanted to skin it cause the fur was sparkly with frost. I still feel bad for that poor cat 🤣

[@abhimaanmayadam5713]

This was in Star Wars: Edge of the Empire, so not nat 20s but my friend basically rolled as high as you basically could in this particular circumstance. We were in Mos Shuta in the starter encounter for Edge of the Empire. We're stuck there being chased by stormtroopers. My friend is playing a force sensitive smuggler, his first time playing any tabletop. All the other party members were running towards the spaceport and we were buying time in a firefight. He has the big brain idea of knocking over the water tower to block the stormtroopers rapidly setting up a heavy repeating blaster as it was me and him left closest to the stormtroopers. Bro gets 4 successes and several advanrages when he rolls. So basically he nails the frag grenade throw. Grenade blows up, water tower falls over, washing away the sergeant, knocking over the ERB and the stormtroopers setting it up, and frying the guns of two storm troopers. We book it back to the spaceport, pry off the docking clamps and fly off. 10/10 experience. Also this happened last week.

[@lordbiscuitthetossable5352]

Awesome! I’ve been playing this system for at least 7 years so it’s a good time what those dice can do. ^^

[@WindchargerPrime]

Not the player, but a friend of the DM. A friend of mine had run a one shot for her young daughter and her friend, homebrewing everything for them to make it easier. Her daughter played a weed eater, her daughters friend a Rabbit and she as the DM played a Unicorn at her daughters suggestion. They eventually camp out for the night and hear sounds coming from a nearby cave, they investigate and find a bear eating a large chicken. The DMs daughter then asks the typical Player to DM Question. "Mommy, can my friend, ride the unicorn holding me and we weedeat the bear?" After a few moments of laughter she said roll for it. Natural freaking 20. Needless to say with the simplified combat the bear died and the chicken that wqs dead at this point was hauled to the village so the townsfolk wouldnt starve. Her dad said he had never been so proud, that she asked that one question. As a DM myself I await the day when one of my players asks me to do something chaotic thats just hilarious at the same time.

[@silvanusasher446]

When I played in Curse of strahd, we were playing the death house intro. When my Monk learned of the horrible things that transpired there he took a natural 20 sh!t in the hand of the statue of strahd! A little green Verdan squatting over the hand, making a perfect little soft serve curl at the top!

[@jackharris1564]

In a campaign a friend of mine hosted, my character became the protagonist due to his insane luck. One mission in the campaign involved us to kill a man that aided in supplying the armies of the main antagonist, who was described with the heaviest British accent and the most yellow teeth on earth. After we snuck onto the ship with conveniently shaped barrels for each of our characters, we had to find this man, which wasn't an easy task, as this wasn't the average trade ship as this ship was gigantic like those ships that carry containers from country to country. After a while we find his quarters probably after several close shaves with guards and crew members. We enter the quarters to find he's not there. So the gnome in our party suggests to ransack his quarters, steal his money, destroy papers, etc. Eventually he enters his quarters, and see the mess we've made, and after he enters the room in ask the DM 'Can I punch him in the face?' or something along the lines. nat 20 My character begins to do a few stretches. 'What are you doing?' he asked. 'Stretching' I said back. 'For what?'. 'This'. I clock him in the face with all my strength, collapse on the floor, dead. My punch was so strong that I caused this man's face to collapse in on itself.

[@MattHedgern]

Just had one of these happen! In a previous session, my lizardfolk barbarian Karnos found a magically enhanced greatsword, giving it some extra damage. Turns out, not the only effect it gets. We faced off today against some goopy slime guys (idk what they're called) that slowly erode any physical weapon used against them. When it was Karnos' turn to face one, I initially thought to slam it down with my warhammer (my main weapon so far), it's not like I had anything better to do. But wait, I just got an enchanted sword. But wait, I don't wanna erode the thing I just got. But wait, can a magic weapon even erode? DM asks to roll Arcana (which I had -1 in), natural 20. Bro has no idea what a magic is, but he's sure that his fancy new toy not only hits even harder than normal, but straight-up can not break. I then proceed to one-shot not one, but two slimes in a row with what I can only imagine was some full-on Monster Hunter greatsword combo shenanigans. One of my party members started calling me The Slayer after that.

[@mifigor1935]

Our rogue failed a check to lean out of balcony. Then succeeded a dex save to land safely, fell straight into a lap of a guard sitting below it and rolled a nat 20 on seduce check while Barbarian turned the other one into a bloody explosion because he thought it was supposed to be a surprise attack (he also rolled nat 20 and max damage)

[@AkaTrios]

I am the kind of DM who lets players do even dumb rolls, like making a Strength Check to see whether they can open the door of a rather ruined building. The idea is to have them roll on many things, not just a few super important ones, so that they won't know when a roll might have major consequences or not so they are hit harder by the result when I intend them to be. Anyways, in the first session of my campaign (which btw is also the first campaign I am actually doing, rather new to DnD) with my friends, one of them tried to open the aforementioned door of a rather ruined building. I chuckled, because that player has a rather bad Strength Modifier, so I let her roll the Strength Check and... well Nat 20. As Nat 20s go, I want to make the non-important ones at least hilarious and over the top, so we can all have a laugh, so our Warlock/Sorcerer with a Strength Modifier of -3 RIPPED OUT THE DOOR, shingles and all, in a display of strength that would have somewhat unsettled the party, if they were there already (this is before the party met). Her Nat 20 was the first roll in the game, and it immediatelly showed my players how I'd go about d20 rolls. Campaign's still ongoing and while we're all still learning about DMing and Character/Role Playing, we're having a blast.

[@goji3755]

Whenever a party member asks my character to sneak ahead and scout enemy territory or do some sabotage, I usually roll stealth without saying anything in character. Sometimes I roll a nat 20 and the DM rules that the character making the request looked away for a split second in the middle of their sentence and when they looked back I'm gone. So yeah, my character has a habit of pulling a Batman.

[@lulubelle0318]

So I just finished running a session of Lost Mine of Phandelver (spoiler alert for that adventure) for a few friends. The party met up with a group of redband ruffians and our fighter asked to kick one of the ruffians in the nuts. He rolled a Nat 20. Later at the ruffians' hideout, two of the enemies the party was fighting died to two Nat 20s the first got decapitated while the second got kicked in the nuts.

[@Victor-056]

11:50 The DM clearly had fun making a Warlock act like Monkey D Luffy...

[@ChristebelCoertze]

In my nat 20 I played as a Satyr bard who collects skulls to talk to the ghosts inside, my party got attacked and none of the attackers noticed me so I rolled a nat 20 to chuck the head at an enemy and as I did I shouted "Good morning Farun!" and it instantly killed the guy it hit XD. Everyone in the party then collected skulls for me like it was going out of fashion. lol

[@brycebarraclough9365]

One of my favourites was my first official campaign, it was only one session after which everyone but me lost interest but it was still quite fun! I initially planned to create a kenku necromancer themed off of a great horned owl, he was massive figure wearing a crooked plague doctor mask and massive robes made out of rags that made him even larger. He was going to be a necromancer but after some forceful advice from a friend on the difficulties of playing a necromancer and the uselessness of a scythe he became a truly monstrous tank wielding a great hammer and having an armour class so high there might have only been one enemy that actually managed to roll high enough to hit him in the time I played as him. The session had us wake up in a bandit camp as prisoners shackled without weapons. My kenku with little effort managed to snap his and the other party members chains like paper, and through misunderstanding a party members plan to sneak by a crowd of sleeping bandits he used the same chains to strangle a bandit to death in their sleep which led to a combat encounter. In this fight we abused the mechanics of a door to kill these bandits, For context our dm ruled that opening a door costed an action, the bandits only had one action so upon opening the door and going through it, the door would be promptly closed behind them and as consequence they would be isolated and murdered. Though the greatest moment was at the end of the session after freeing some other prisoners there was an open stretch of land before freedom, I didn’t trust this and rolled to find the “saddest most eager looking to escape” prisoner of those we saved and upon doing so I told him to run ahead to freedom, my suspicions were proved true when he was viciously mauled and killed by the bandit chief’s pet bear who was hidden behind a tent Truly a fun time.

[@sokandueler9578]

We were running Rime of the Frost Maiden while our DM compiled material for the next arc in our home brew campaign. My friend was playing a Tortle Druid (my DM gave us all warm clothes to start out so we didn’t get bogged down with con saves in the cold) who was an absolute stoner. We go in to investigate a murder in this cabin, and the guard stops us at the door. “Papers please, only official investigators allowed.” The tortle, without missing a beat, walks up and hands the man a blunt and says “here’re my papers.” Nat 20. The guard takes the blunt, walks off, and we go into the house to check out the murder scene.

[@johntatman7477]

I used to be the National Secretary for 'The Guild of Melee & Magic' an association of around seven clubs scattered across SE England. As such I'd try an visit different branches when ever I could. So I did the London Club and they squeezed me and my Half Elf Ranger into a group. Party is sneaking down a corridor, trap triggers and we all slide down (me first) into a huge underground cavern with a lake. In the gloom the monster of the depths rises up so I do what any self respecting person would, tried to hit it and rolled a natural 20. At that point crits were new and I'd never encountered them before, so ask 'Now What?' 'Roll again' So I got another twenty followed by an eighteen and did some insane damage. DM's party challenge monster gets split in half with a single blow. Never mind, quick thinking the water stirs and a second creature starts to raise up.. Giving me the chance for the classic line, 'I've killed mine, this ones all yours'

[@HyperJohnua]

So in my game, bloodstone isle a rollmaster darkmaster pirate themed games our himebase was under the effect where the gm could decide if he wanted to rotate our dice or not, d100 so a 69 would be a 96, the rolls are open ended 96-100 is our nat 20 I roll for deceive to make a disguise shadowmage (F), i roll a 69 and he tells me to flip them and reroll, i respond "you just dont want me to say *click* noice" i reroll and roll a 99 and tell me "ha flip those! I dare you" after another reroll i end up with the piints i put into my skill and the rolls i made 300+ my 6 foot tall half elf(ish) girl leaves an a 7 foot tall orange tree man with bush hair comes out. It was a pointless roll but i still loved it.

[@andrewmoore2580]

My brother rolled to see if his character got a hangover from drinking once, First nat 20 of the first champaign i ever played. He has since discarded that character and came up with the exscuse that he went to fight a dragon and never returned.

[@brittg7131]

I was a longtime player who decided to GM for the first time. I decided to run The Dragon's Demand, a module for Pathfinder 1e. The party beat a miniboss and received a treasure: an Amulet of Mighty Blows. Nobody in the party was really built to do unarmed strikes or natural attacks, and selling items was off the table for the moment because of plot developments, so there was some debate about who should get it. Well, there was a catfolk wizard who happened to have the feat Improved Unarmed Strike (only to qualify for Deflect Arrows), who thus argued that he should get the amulet. The rest of the party was skeptical about this, because he is a wizard. To support his argument, he said he wanted to throw out a few punches as a demonstration, so I said, "OK, make an attack roll. Of course, he got a natural 20. I said "For just a moment, you managed to look like a prize boxer." Everyone else in the party was suitably impressed and conceded the amulet to him. After that, I think he might have thrown like one punch at a rank-and-file enemy before they faced the final boss of the module.

[@usr3773a]

I think we were playing Strad (rescuing prisoners in a church in a town under siege). After clearing the dungeons (mostly) out party of 8 was ready to leave. We'd made the mistake of splitting the party in the beginning and a mimic had seriously damaged 3 players before it ran away. I told everyone to hold on since I wanted to go find it. Found it majorly wounded in a corner. I got close to it and told if if it behaved, I'd take good care of it. Got a Nat 20, everyone including the DM dropped a lot in their pants and I got a 2D4+4 Mimic sword. Bad part? a few months later, found 2 mimics in a room and drove them into a corner in a room full of flammable items and told them to serve me of burn to death. Nat 20. This DM had heard the previous story and each round I faced them, he knew what I was planning. So once I rolled it, he said. "They choose to serve you, they kill all the enemies in the dungeon, end of game" I am the reason Mimics arent allowed in future games

[@AlfredDoe]

Free act of service, get away from my pants😅🤣😂😆

[@aaronkoss8001]

This was back in 2010 when I went to Job Corps in my state. I was first introduced to D&D 3.5 by my now great friend Matt. He was the DM. He is an awesome DM but harsh with XP. We played with 3 others for a total of 5. To show you how harsh he was with XP, our first month of play, mind you this was after our classes ended at 3: 1-We go to the Rec building and hog a room to ourselves and start playing until dinner at 5 or 5:30 and pause the game. 2-Spend an hour at the cafeteria and go back. 3-Play until Rec closes at 9. We did this for a month straight, 7 days a week. At best, 5 hours a day for 30 days. Yes I know, it was f*cking great...BUUUUTTTTTT!!!!! We went from Level 1 to level 3 in that time. Anyways to the story you all want. We managed to get to Hell and meet Asmodeus. We were at level 8. Our Bard, for some messed up reason, decided he wanted to *attack* Asmodeus to see if he really was powerful. Matt, our DM, told him to roll for attack. Nat f*cking 20. We all were shocked with our eyes wide. At the time, I was not sure if this was a rule Matt made up to correct it but he asked roll again to confirm crit meaning he needed to roll a 19 or 20 to do extra damage. Bard rolled 20. Another f*cking Nat 20. Crit confirmed. Defeated, Matt gave in to our cheer and said "F*ck It" roll d20 again. 3 Nat 20s in a row. Level 8 bard vs Asmodeus. ASMODEUS! What was the result of 3 Nat 20s you may ask? We looked to Matt with his face redder then a tomato glaring at our Bard. With a tried calm breath he asked, "How did you kill him?" We all screamed and cheered. If you this stops here, think again. Bards are notorious for the """flirting""" Even as new players, somehow our Bard still kinda followed this. He discribe that he ran to our fighter, jump from our fighters back towards Asmodeus and took out his d*ck and mid-air d*ck smack Asmodeus in the face. Asmodeus died by shock that a mortal dared to do this to him and just died. Heart attack? Idk but he just died. Our Bards response to this? "Our mortal women takes d*ck better then Gods".

[@conecarina2566]

I made a Gloom Stalker Ranger in my latest campaign, originally it was going to be a Druid but I swapped for party composition purposes, and boy am i glad I did. I would get a Nat 20 attack on every first turn of every single fight and blow the pants off the enemies up until last session, note how Gloom Stalkers have the funky property of having an extra attack on their first turn that deals +1d8 extra damage, meaning that with my Heavy Crossbow (since i can attack only once per turn pre-Crossbow Expert) was dealing 2d10 + 2d8 + 4(Dex) piercing damage every first turn of every combat.

[@mkklassicmk3895]

Wouldn't it be the "Sledge-a-Gnomic."

[@aurorialgaming1935]

Can we get a horror reading in the voice you used for "go back to sleep."?

[@TheMakman91]

I feel for the guy who had their DM quit on them. I had one more devastating. He deleted the discord server and all of our games. Thankfully we recovered from that.

[@akbarrezvani6393]

we rolled a nat 20 + 4 on guidance on our survival check to find the way to our destination (32 result) and found 2 extra pathways to other destination. we thought they all end up to our destination but we were wrong and chose the wrong path. literally rolled too good for our own good.

[@StarkSpider24]

Had an NPC I convinced to not tell anyone what we were up to. The NPC suggested I give him a punch to “make it look good” I roll a natural 20 unarmed strike and knock him flat out.. he woke up with legit amnesia 😅

[@K4RN4GE911]

My group and I were sidetracked by a group of 4 goblins taking potshots at us from an overturned shipwreck near the coast. We fought our way into the mostly intact interior, getting a couple of good hits in. Our Tiefling at the time, an Artificer, rolled high on Hellish Rebuke, lighting the toughest one on fire. What happened next will stay with me until the day I die: Said goblin was up and despite the disadvantage, rolled crit on acrobatics. As it turns out, this group of goblins were an ex group of wrestlers that turned to crime and their leader proceeded to deliver a *FLAMING **_DROPKICK_* to the Artificer! The DM later drew a picture of it, I HAVE PROOF!

[@becca7410]

I have only rolled a nat 20 once, and it was to see if there was anything else besides soup in a cupboard.

[@murderdrones-obsessed-cat]

Playing a space themed campaign. We're going to take a carrier ship to retrieve something from a lake. I'm playing a blind character, and out of boredom I rolled to sniff the vehical we were going to drive, and I got a natural 20, and received a very detailed description of it. Unfortunately it wasn't too useful, but still very funny.

[@BIGTHECAAAT3863]

So the part is defending a village from a gang of ratfoll and in the epic final confrontation the rabbit folk fighter rallied the villagers to fight with us. The fight was going pretty bad until one farmer with a pitchfork stars going ham on the minions. After he finished with them he did a flip over our Goliath tank and kicked the bos in the jaw getting his attention. Somehow despite having an ac of about 10 and easily with one-shot range of a barbarian boss he holds his ground and rolls a total of 3 nat 20s in the fight. Later we find out that his name is Tom Denzel. As a joke one party member asks if the pitchfork is a magic relic. The dm rolls to see if the farmer is lucky enough to have a magic weapon, and gets another natural 20. So now we have Tom the monk with an ancient magical trident passed down from his parents, we found the main character.

[@dedmenwalk]

My first game on DnD, I was a Lv 1 in a campaign that had ran from about a year, and everyone else was around Lv 15-20. We ran into hellhounds that would oneshot me, so they told me to hang back and gave me a bow. I decided that I wanted to be in the action, so I asked if I could roll an animal handling check to see if I could tame the hellhounds as a joke. The DM laughs and decides to allow it, but tells me that I need to roll very high. Nat 20. The rest of the campaign, I had 3 hellhounds attacking on my command, which unfortunately ruined the final boss as I just sent the hellhounds to die but they got enough damage for a singular bow shot to take it out.

[@noneofyourbuisness1679]

If you’re for online speculative evolution projects, one of, if not the most famous would be “Serina” by Dylan Bajda or Sheather888. It’s a currently ongoing project (albeit nearing its end) that toys with the concept of seed worlds - planets populated by only a handful of species to see just what evolution will do with so much freedom. Serina in particular deals with a world populated by only a single terrestrial vertebrates, the domestic canary, and the species necessary to support them. It’s a massive project several years in the making that has seen the rise and fall of numerous, sapient species across epoch-spanning stories. And yet, they occasionally touch upon individuals and the world-changing consequences of their actions that have led to unparalleled periods of prosperity and entire mass extinctions.

[@braydentreleaven9370]

One of our second times ever playing dnd went and I had one of these moments I guess, so the dm was trying to make this op villain (they didn’t understand how to do it really) so he created a literal time god, after getting a little mad at our warforged, the time god flat out just killed him. Our bard, in the most stereotypical way possible, said he wanted to seduce the literal god. Somehow succeeded, and made him go back in time to when the warforged was still alive

[@darebrained]

Shadowrun 5th Edition: Not nat20 (as those don't exist in the game), but after the GM lamented my choice of weapon - using bow and arrow in a cyberpunk setting is, I guess, a bit out of the ordinary - I made him eat his words. (And just for the record, no he isn't a bad DM, just wanted to be an asshat about it or cared about "REEULIZM", it was that he thought bow & arrow just weren't very good and that the character I made that was supposed to be semi-combat focused would not be able to pull his weight and cause problems down the line. This did happen with another character of mine before so I do not blame him at all.) It was a 2 player run and the introduction for the other person we were playing with, so we kept it simple: Escort this truck through the city. Obviously we got into an ambush, but the truck being quite sturdy had no problem to just keep on trucking. Suddenly a guy with a rocket launcher showed up, but due to a perk I picked up I would always go first in the first round of combat. Since I realized that if I wouldn't kill him we'd be in it deep, I decided to use one point of Edge (explanation below) on the attack roll to expand my dicepool to, IIRC - been a while - 20something d6 and to roll a ridiculous amounts of hits. The GM's eyes going between my shit eating grin and the result, and after taking a moment to come to terms with what he just saw confirming the hit and asking for the damage. *And it was at this moment he knew: He fucked up.* As the shot wasn't just going to injure his rocketman, or put him into bleedout. That arrow would come out on the other side, with basically half of his spine still attached. That guy was turbodead. And we were just 10 minutes in. And if that guy dies we wouldn't be in it for more than another 5. So he decided that the impact of the arrow would trigger the rocket and blow the truck anyway, which wasn't exactly RAW (for once NPCs can't edge (again, explanation below) and the rocket launcher he used did not have a physical trigger, so it wasn't like that the shock would make him curl his fingers do shit), but let's be honest while it would've been kinda cool for me, I completely get that this run wasn't about me, it was to show the new guy the ropes and having the whole thing be over in less than 15 minutes after multiple hours of character creation would've sucked, so while this might not have the results I intented at the time, I do agree with my GM's handling of the situation. Still that face was priceless. Only beat by the face he made when I started using poison tipped arrows half an hour later and he realized that poison was kinda very good. *= EDGE is a stat in Shadowrun, for all intents and purposes it is luck, however you do not roll for it, rather than that you can expend edge points in order to help yourself with rolls, prevent yourself from instant death and so on. To go into more details: Edge points can be either spent (means they will regenerate, think spell slots) or burnt (means the edge stat will be decreased by 1 and you have to again invest to karma pts into it to raise it back up; karma being basically XP but instead of levels shadowrun just has you spend karma directly to increase stats or learn skills). Spending edge can do the following: - Increase your initiative dicepool to 5d6 (the maximum) for one round of combat - Make a critical glitch into a regular glitch or negate a regular glitch (the equivalent of critical fail; basically everything in SR5 is rolled with d6, should half or more of your dicepool show 1s it is a glitch and should you have that and no 5 or 6 you have a critical glitch on your hands) - Add your total edge stat to your next dicepool *and* ignore hit limits (many rolls in shadowrun have a limit of how many hits (5s and 6s) you are allowed to count - this is what I did and commonly referred to as "preroll edge" - Rerolling all dice that didn't hit (so all 1s to 4s; and yes usually this is straight up better than "defusing a glitch" as you rarely will have such bad luck again) (=postroll edge) - Being first in the next round of initiative (one round of combat has multiple rounds of initiative), this is basically the same as the perk I have that I mentioned, though doing so would trump my perk - One final action if you are about to go unconscious or die And you can burn edge for - Automatically passing a check with 4 nethits over the opposed roll or threshold (whatever is applicable) - Not dying. Obviously it is GM's discretion what they allow, especially with burning edge. Also an important note here: You can burn edge that you already spent, so even if you spent all your edge already you still have the option to burn it to either succeed an (near-)impossible check or to survive otherwise certain death. (It does not work the other way around.)

[@hailliel7307]

I’m a new DM and in a session that we had today, our lvl 1 Dragonborn fighter found a hollow metal cube that clearly had something inside. He rolled to break it w/his Morningstar and got Nat 1 so I said it bounced back to hit him and told him to roll to hit himself. He rolled a Nat 20 and rolled max dmg- thus hitting himself in the face & knocking himself to 0 hit points. Luckily they were in a long rest. Edit: I want to add, he had just escaped form the party’s encounter with a phase spider UNSCATHED.

[@soulocinder3598]

So I play a big ol barbarian red dragonborn that pulls the stagecoach the party travels in. We were visiting the wizard who hired us, and our warlock went to the enchantment table to give his coat some extra spell juice. He failed about 5 times in a row, which eventually caused an explosion, drawing my barbarian's attention. Warlock went to try one more time, but I decided to try to help him as a conduit for his magic, despite having only a +1 in arcana. I rolled a nat 20. DM decided to give the warlock the spell: Armor of Agathys, and my barbarian got it as a natural ability he could cast. This is the story of how a flame oriented lizard man learned an ice spell he had no right learning.

[@eternasapphiremoon81]

Oh I have a few Nat 20 moments... One of our friends was doing a tower scenario, and our group had just gotten ourselves out of a maze where weirdly enough, we swapped bodies. I was playing a bronze Dragonborn barbarian, who - coincidentally enough - had my body/mind swapped with our Goliath Barbarian. During a fight before coming out of said maze, he had out my dagger + 1...so when we switched back to our normal selves and jumped into the next battle - against 3 giant spiders and 5 normal spiders - I had that dagger in hand. Fight proceeds as normal; we're down to one rather annoyingly evasive normal spider, and my turn comes up. NAT 20! So here I am, bronze Dragonborn with dagger in hand, STORMING over to this little arachnid and literally STABBING this thing into a pile of goo yelling "DIE! DIE! DIE!!" Second story: we're doing an Odyssey of Theros campaign - which is Greco-roman inspired. Our friend - a human rogue - is trying to sneak back to team back up with us again, and comes across a 2-headed dog. DM rolls for Perception - once for each head. First head gets a Nat 20, so that head's lunging forward, sensing our rogue friend. The other head...NAT 1!!! So Head #1's going on and yelping up a storm, but Head #2's like 'nope' and is licking itself! Our group laughed for a good while before continuing the trek but WOW! ROFL!

[@sparrowfrank8364]

The character I’m playing right now generally doesn’t confront his feelings an is really good at pretending he’s fine. Our monk rolled insight to see if he was actually okay and rolled a nat 20 with +4. I rolled deception to try and keep the mask up, and rolled a nat 20 with +10

[@d1nodray]

I'm new to DMing. I have a level 1 party, and I improvised in a bandit camp on our way to the first dungeon. There were 5 in total. Most of our party of 3 did the smart thing, and went around. Our fighter, on the other hand... He jump attacked the bandits (who I actually rolled health for, and somehow got almost entirely 7s.) The first guy takes 4 damage from a sneak attack. The rest of the party then jumps in. They proceeded to kill my tiny bandit camp. At one point, the fighter got a nat 20. I sighed, and said "roll for damage." All he said was "this poor guy..." Proceeds to roll up 20 damage. The guy was level 1, and rolled 20 damage onto a creature who only had 7 health to begin with. This was 5 days ago and I'm still confused.

[@Barrystue]

This just happened, but at a dnd club at my school, we were doing a campaign set in the one piece universe. I had been fishing when I was attacked by a giant bobbit worm thing. I end up washing up on shore next to the fish I caught. I immediatly scarf it all down raw, to see whether I did it without getting sick, I rolled a nat 20. I said as a joke “maybe there was a devil fruit in one of them” The DM rolls to see whether there was (you’d roll 5 d20s and if it was over 70 you’d get one) And he rolled a 71 The whole group started bursting out laughing. I guess I’m gonna have to see how well I do with it.

[@KeirKee]

Don't remember if it was a nat 20 but my Kobold Bard cast Tasha's Hideous Laughter on a Kraken and succeeded, The Kraken laughed under water and attempting to stabilize itself, sunk the ship and went away.

[@SpeedyCheetahCub]

In Just Roll With It: Apotheosis there was a moment that I think fits here. It wasn't funny at the time it happened, but in hindsight it is pretty funny and it actually was helpful to get the good ending of the story. So the party was fighting one of the bosses when it casts a spell causing the Paladin to see everyone as enemies and attack someone at random on his next turn. The thing is, he was holding a Life-Stealing sword. The rules of the sword were if you crit any creature who has less than 100HP and they fail a DC 15 Wisdom save, their soul is ripped from their body and they die instantly. And the Warlock had 93HP (it was somewhere in the 90s, not sure if it was exactly 93). So on his turn, the Paladin rolls a d6, 1 or 2 being to attack the boss, 3 or 4 to attack the Bard, and 5 or 6 to attack the Warlock. He got a 5. So he rolled his attack and got... a Nat 20. The players started getting nervous at this point, and the Warlock had +4 to Wisdom saves so he needed to roll at least a Nat 11 to succeed. He rolled a Nat 7, getting 11 total. And instantly dropped dead. The party started freaking out, and the player was upset, especially because just before that they were playing in one of their other campaigns and his character drew the Donjon card from the Deck of Many Things, so he lost 2 characters with a few weeks. Fortunately, this event actually allowed everyone to have some much-needed character development. The Warlock and his patron both got sucked into the sword, where he got to have an epic battle with them in order to take back control of his life. The Bard realized that they didn't know everything and weren't perfect. The Paladin learned how to cope with the loss of a close trusted friend. By the time the Warlock was revived, the party members were able to have a real conversation and went into the final session as a united front instead of still being at odds about their plans for after they defeated the BBEG. Instead of the final session being them defeating the BBEG and then having a 3-way PVP encounter ending in two of their characters dying and the third one causing something terrible to happen (the plans that the Paladin, Bard, and the Warlock's patron had were each different but were all bad), they had a really wholesome moment and ended up going with the Warlock's plan, which was super chill.

[@mikidarabos2357]

Our rogue invented C4

[@disableddragonborn]

Recently, on a whim, I decided to roll a perception check with the DnDBeyond digital dice. Nat 20. I haven't had a group to play with in a few years. This was my first Nat 20, and it wasn't even for a campaign. I used the digital dice for most of my time with my old group (I lost the D20 of my only actual dice set) and it consistently gave me awful rolls. Granted, I did it with a character I never actually got to play. Me. I used a D&D IRL stats quiz to make myself as an NPC and potential replacement for my first character, who I made myself the spouse of. That quiz required a LOT of fudging for me as a person in a wheelchair (I don't fucking know how much I can bench press!) so I'm somewhat skeptical of the results.

[@TheVoicesOfTheBeyond]

Two stories of Nat 20s here; in my very first session, my dumbass nearly got myself killed. I was playing a Fire Genasi, and the setting was summer camp. At some point, a curse descended upon the camp, and the sources were five streams of light. I ended up in the party that was heading towards the lake, where a water maze had formed. Cut to fifteen minutes later. We've ran into every dead end possible in this damn maze, and my character gets frustrated. She says, fuck it, and tries to walk through a wall of what looks like stagnant water. I've got a +6 bonus to Athletics, so I'm certain I can pull this off. I try to power through... Only to be reminded of something critical... MY CHARACTER CAN'T SWIM. My character almost drowns, but two of the other characters pull her away. They roll... And the weaker of the two rolls a Nat 20. Later in the maze, my group comes to a chest buried in the ground. They determine that I should do it, I roll... And I get a Nat 20. So my character, who nearly drowned TWO MINUTES AGO, rips a whole ass heavy chest out of the ground without effort.

[@dr.nowhere8905]

We were fighting a dragon who was under Demon possession. Our fighter decided to throw my goblin barbarian at him. The problem was that he was more than 300 ft in the air at the time, but the dice God's granted him a D20 to hurl my 4 foot 2 ass right in his face. Now, my goblin has a sword that does more damage when he kills something, and he was currently at Max Kills, meaning I was racking up insane dmg numbers, I proceeded to spin like a beyblade and devided that dragon with a 27 to hit and rolling max damage.

[@georgel7195]

one time i rolled to catch a squirrel i got a nat 20 and caught it perfectly

[@zapachehelicopter5163]

*Dumb goblin like guards looking for us as we descent in an elevator* * "They went that way!* *Me with a nat 20 in deception* "No we didn't" "Oh, okay! Thank you!"

[@RedxMage007]

That last story is totaly a "One Piece" moment

[@Bookwyrm1209]

First session of the campaign. I'm playing a 6' 4" half-elf bard with the lowest strength stat of the party. We also have a half-orc ranger (7') Tabaxi rogue (3' 2") and half-ling fighter (2' 11") We're trying to join an army to track down the organization that sent a tarrasque to destroy our hometown. Our half-orc is intimidating the heck out of the commander because he wants to lead the army. I'm trying to diffuse the tension in the room to little success. Our halfling decides he has something to say and pushes me out of the way. DM has him roll. Nat 20. He has me roll to resist. Nat 1. This not even 3' tall halfling sends me FLYING 20 ft to the far wall. Immediately after, one of the guards in the room picks him up by the arms and handcuffs him. Greatest first session I've ever played.

[@jojogacha974]

Aight so in my campaign we were doing a tournament thing and one of the villains was watching over us and sent this hybrid of a bunch of monsters at us now there was this dark elf and was supposed to weaken it but the DM (my brother) rolled a nat 20 so he insta killed it. I would love to see that kind of thing in a game lol

[@dragonickmaster]

I don't fully remember if this is a Nat 20 moment but I'm pretty sure it was. I was playing a Fey Wanderer Kitsune Ranger called Mai Darkbolt who's Heavy Crossbow had been reflavored into a Xenoblade Chronicle looking riffle. We had a plan to ambush some assassins/spies, and I had Mai hide in a tree. Rolled well on initiative, used Hunter's Mark on an assassins, and rolled a nat 20 to hit so combined the Hunter's Mark, Dreadful Strikes and normal heavy crossbow damage... the last thing that assassin saw was the red dot from Hunter's mark showing exactly where it would hit... right over his heart and the only thing he could say was 'oh fuck' and boom. no more assassin

[@rauhillah3884]

Assassin Rogue nit supposed to have guaranteed crit on advantage roll. They just have guaranteed crit on every hits dealt to surprised enemies.

[@Diablo-xx9gx]

In a old game the party were investigating a long dead wizard's room, found a portable hole folded up. Open it and a small but powerful group of demons emerged. They been trapped in it for centuries by the wizard. I playing a elven mage archer flipped a table dived behind it. Freaked out, the demons spared us as we freed them and got ready to head home and fight in the blood wars or something. The demon leader a very powerful demon goes. COME ON BOYS WE GOT SOME KILLING TO DO! I freaked out thinking meant us so I shot at him. The DM groaned covered his face, and said roll then., I did got a nat 20 re rolled got another so was a instant kill. he covered his face again as I whooped and everyone laughed. Took him out damaged the other demons due to the shock wave of the explosion he made, and we finished them off and got somee good exp.

[@Tis_a_YOUsless_Shroom]

So I’ve been going to a semi-serious, semi-joke campaign with 6 players. This day, 3 people were missing, so our DM ran a mini adventure. The cast was: Variant Human Tempest Cleric (me), Gold Dragonborn Eldritch Knight, and full Orc Barbarian. While brainstorming what mini adventure to run, our Eldritch Knight started talking about Minecraft (it was an ongoing joke in our campaign to make random Minecraft references) and he starts saying that he and his brother used to play Minecraft and he very vividly remembers gathering an entire army of dogs and giving them to his brother. A while later, his brother accidentally hit him and the army attacked. This monster murdered a ton of dogs. All of us were accusing him of murder and demanding him to be on trial, to which our DM slammed the Monster Manual shut, looked at us evilly, and asked, “How many dogs did you kill?” The Eldritch Knight replied somewhere around 30, and our DM sent a pack of 30 hellhounds at us (there were only 5 at first, but after getting them to low HP, they left to get reinforcements. Also we were relatively high lvl) we managed to wipe them out pretty easily (a few Thunderbolts and Magic Missiles later), and there was only one left. Our DM described how a magical force swept us off of our feet and away from the dog, leaving only our Dragonborn Eldritch Knight. “Tell me, what did you name these dogs?” He listed a few names, including one named after himself, and then the DM raised his hand and said, “A shadow looms over the Hellhound’s body. It’s eyes seem to glint with passion and revenge. He takes a step closer, and you (Eldritch Knight) feel a demonic voice speaking in your head. ‘Hello, old friend. I’ve been waiting for this moment.’” And then the dog lunges at him to bite him. The dog rolls a nat 1. Then the Eldritch Knight attacks. Nat 1. Again and again, everybody keeps rolling nat 1’s, until, finally, our DM rolls the dice and says “This will be the time you die” in the demonic voice. He dropped the dice. NAT. 20. We all burst out laughing. The Eldritch Knight was nearly dead, maybe on 7 HP or something, until (ooc) the player remembered something. He also had an army of dogs that he didn’t kill. He begs the DM to let them rescue him, and our DM says that if he can roll a nat 20, the army will come to save him. Guess what? Nat 20. Instantly, an army of Blink dogs tear through the fog and jump at the hellhound, killing it. We all cheered and laughed for a while. That was really crazy. Now our Druid is keeping one as a familiar. His name is Jeremy.

[@vasheskaaronsar1568]

Intimidation roll 20 Party: Let us pass 😉 Rookie necromancer: I'll tell my master! I'll complain to him! I'll tell him everything! Party: Ok, whatever. Undead: LMAO 🤣 DM: *facepalm* Another battle map to waste. And like that we ride into sunset without tough fight. Golden 20 roll for bard. Insults, mockery and other songs turn serious dark fantasy into Benny Hills show. I can tell stories like what forever.

[@vtfan115]

What's a "dirty" nat 20?

[@BrianVaughnVA]

I think a dirty "nat 20" is just a misunderstanding of what a dirty 20 is (since everyone says NAT in front of it) - but I imagine it means you get the 20 by adding up your bonuses.

[@vtfan115]

@@BrianVaughnVA ok I thought it might have meant that the person cheated.