D&D Players, What was your funniest “nat 20” moment? #6

Put your stories in the comments below they could be in our next video! If you have your own video ideas submit them to us on Reddit at r/MrRipper
Stay tuned for more awesome DnD content!
/ mrripperstream
/ mrripper
/ mrripperyt1
/ discord
Source
/ if_you_decide_to_do_an...
#mrripper #dnd #dndstories
Stay tuned for more awesome DnD content!
D&D players, what way did you use a "useless" spell in a good way? #2
D&D Players, What was your best "Wait...what?!" moment?
What's the biggest mind-f**k you've seen during a DND campaign?
What's your worst loot stories?
What's the saddest death that you have ever encountered while playing D&D?
What's the funniest way you spoiled a important plot element in your campaign?
DND players, what was your funniest “rolled a 1” moment?
DMs, What is a plotline you've always wanted to run?
Ever had another PC kill your character?
DND Players, What is the coolest character you have ever played?
DND players, what was your funniest “nat 20” moment? (r/askreddit)
DND players, what’s your best Stories of Rope? (r/dndstories)
D&D Players, what's the most screwed up thing you've ever done in a game?
What's the worst TPK you've experienced?
D&D Players, what's the most screwed up thing you've ever done in a game?
DND Nope Moments #1
What’s your best Tarrasque story?
What's the funniest thing PC's latched onto?
What is the most unexpected damage you've ever done as a PC or DM?
What is the smallest way your DM has driven home how "evil" a villain is?

[@captainpolar2343]

I rolled a 20 'trying to give one party member 1 coin' it was hilarious

[@BrianVaughnVA]

I imagine if you failed then you literally dumped your purse on them and said - "I'M SURE I HAVE EXACTLY ONE SILVER HERE SOMEWHERE!"

[@Sleepy_Cabbage]

@@BrianVaughnVA *screams and tosses the purse at their face causing it to explode into a pile of silver pennys*

[@BrianVaughnVA]

@@Sleepy_Cabbage "GOD DAMN IT WE'RE RICH!!!"

[@gengarzilla1685]

"You throw that coin a thousand feet into the air, catch it flawlessly, and point it to **insert name here** as though this coin was an important quest item."

[@deepseastonecore3017]

A star walks into a black hole but doesn't seen phased. The black hole then turns to the star and says, "I don't think you understand the gravity of this situation."

[@BrianVaughnVA]

THERE'S NO TURNING BACK ONCE YOU SEE... THE EVENT... HORIZON....

[@esppupsnkits4560]

Dad jokes are nice

[@BrianVaughnVA]

@@esppupsnkits4560 Welcome to 90% of my streams on Twitch, dad jokes in Arnold Schwarzenegger's voice.

[@tincat2347]

Haha, Ok that joke is out of this world

[@geoxaga6507]

I'm so glad you brought it back, now you you just need to bring back nat 1 stories. I remember this one story you did with the adventurer and goblin, where they both got multiple nat 1s and it ends with "Pack your stuff and leave, I'll tell the people who hired me that I killed you. And we both agree, this never happened." He agreed.

[@EinTeufelskreis]

I rolled a Nat20 that prevented two PCs (including my first ever DnD character ever) from dying. We were travelling a frozen mountain range when we were attacked by two ice worms. After we killed off the first one our dwarf paladin got attacked by the second much larger worm, failed a strength save and got swallowed as a whole. My dragonborn paladin got into meelee combat to try and save his companion, but got unlucky and swallowed as well. Inside the stomach of the ice worm we found out that we were taking acid damage by the digestive juices of the worm, which rendered the Dwarf unconscious and my character at 3 HP. The worm - now with his stomach filled - decided he wasn't hungry anymore and decided to retreat, leaving the party unable to save us. My paladin now in full panic mode could only think of one way out (since he was restrained and couldn't attack properly): He reached into the pockets of the Dwarf, pulled out two bottles of moonshine booze the dwarf had bought at a hillbilly bar in the slums of town we visited and poured them into the worms stomach. Our DM (visibly interested in my strategy) warned me that with the con bonus of the worm he would have to roll pretty low for this to go through... he rolled a 3. So then he annouced that we would feel some kind of internal movements inside of the worm as he was starting to vomit. After a second of sheer awe from me he then told me to roll a dex save to see how much damage I got since we were in a tunnel that was basically the size of the worm and he would be steamrolling us. Since the dwarf was unconscious and I was at very low HP (and considering the fact we were seperated from the rest of the group), any damage would have put our lives at serious risk. (Espescially considering the death save the dwarf would have failed automatically) I rolled a Nat20 on my dex save. So as we were catapulted out of the worms stomach my character tucked the dwarf in his heavy armour under his arm, proceeded to make a perfect stunt man roll to not take any falling damage and landed in a small hole that was big enough to dodge the worm going above us. I then stabilized my companion and we were able to rejoin the group. Although the botched con save of the worm was what rescued us in the end, the Nat20 dex save rounded out this combination and spared our characters from gambling for our lives by throwing death saves.

[@DHTheAlaskan]

I was in a pathfinder game where we started a cult around The Banana God among a group of goblins. Because belief in that world was so powerful it brought this minor deity into existence in a nat 20 bluff check. This tropical island was now under the influence of this nanner deity. We were seen as prophets to these goblins.

[@nathanielbass771]

Now all you need is the "Ice Screamer" and baron of beer to summon the mythical Sun Dave ( Ice cream sundae)

[@EmmatheCrazyGirl14]

Thank you for making me laugh hysterically for several minutes!! This comment is just GOLDEN! 🤣

[@maxblake5564]

This Banana God sounds a lot like Blibdoolpoolp of the Kuo-Toa in how it came to be.

[@richarddanielfuller3968]

My funniest Nat 20 goes like this: We'd taken refuge in the local tavern and decided to drink our victory away (we'd killed a couple of cultists, nothing much), and whilst this was happening, my character go drunk and I decided it would be funny to pickpocket the rogue. I rolled what I needed and took their gold pouch, only to be discovered later on at night, as the rogue charged into my room, very angry and very stabby. They rolled to hit, and when I rolled to tr and dodge, I obviously rolled a Nat 1. Sighs. I took 20 points of damage, and was left with 1 HP, when I realised that the bread I slept with (my character had an addiction to bread. Curse you Bards) was flung into the air, and falling rapidly to the ground. With my hands tied up keeping the rogue at bay, I rolled to try and save the bread with my mouth. The DM laughjed and said I would need a Nat 20, and low and behold, i rolled Nat 20. This impressed the party so much I got a round of appluase and an apology from the rogue, who called me badass and had a newfound respect for me, and gave me a healing potion. The entire group was rolling in laughter.

[@pookiedukie4967]

I recall a moment when my during my first campaign our Half-orc fighter named Jerome was carrying our Gnome Wizard Luey on his back and they fell into a spike trap. They rolled dexterity to try and save themselves and Jerome rolled a nat 1 while Luey rolled a nat 20. Anyways Luey (who was missing a leg) did a triple backflip off of Jerome to safety, and Jerome fucking died on the spot.

[@BlackRainRising]

back in college we were in a game where we approach a keep entrance that's completely open out front nothing to hide behind or anything. Our DM ran what he called "exploding dice" where if you roll a 20 you roll again and add it to the 20 plus your bonuses. So out in this clearing, the Halfling Shadowdancer says out loud while holding his arms up in a "Y" shape "I am a tree" then crosses his arms over his chest and bends over at the waist as far as he can and says "the tree is dead", rolls a nat20 then an 18 I think, all in all I think he wound up with a 60 hide in plain sight, not a single one of us saw him so us and the NPC's apparently were convinced that the small tree/bush had always been there

[@walkingtoaster4925]

Fellow player linked this channel and I love it. I might be late but I want to share a story from my first campaign as player a couple years back. I was playing a very short and slim tiefling paladin lady. We were in a town and for some reason a random smith we passed by accused my OC of stealing. She wanted to leave and let it go but the guy insisted, all persuasion and intimidation failed. He finally grabbed her arm and being a very proud person my character wouldn't let that stand. So she slapped him across the face. DM makes me roll unarmed attack. Crit. The guy instantly dies. We hurry away because we have good standing with the nobles in the city and don't want to risk it but the story makes the round among the people. A bit later we enter the beggar's District and some beggar comes up with a cup he shakes asking for donations. My OC reaches for a three silver coins but the guy recognises me as the crazy one who killed that smith and flees, leaving his cup behind. Trying to give him his cup back my character decides to throw it after him. Nat 20 strength. The cup hits him in the head and I end up killing that guy as well. The townsfolk was terrified of my OC.

[@thescowl6971]

Literally happened today and was literally my first ever session. We we're playing The Icewind Dale and I was a late addition to the party. We got to the Auriel fight and the DM asked me what I wanted to do. Being a Glory Paladin I used Guided Bolt and made my first ever attack roll. NAT 20! After rolling for additional damage, that bolt dealt QUADURPLE damage. (68 to be precise) Needless to say she was PISSED at me. TLDR: My first ever attack roll was a Nat 20 that dealt quadruple damage and made a boss's first form a pushover.

[@arthuriangamingyt4889]

you guys are the reason why I play D&D and my first time (yesterday) was a blast and a half can't believe I got a nat 20 after getting 3 nat 1s lol

[@partysnax1984]

In our One Piece campaign, my friend convinced our DM to let him roll for “how skinny my penis is.” Because he thought it would be hilarious to have a long, skinny penis in game. DM obliged, and he of course rolled a nat 20. He officially gained the skinniest penis that a human penis could physically be. He was right. It was hilarious.

[@angelbloodshinra]

Just like the Vine foretold... it's ya boi, Skinny Penis!

[@draco4450]

luffy: look what they have to do to mimic a fraction of my power

[@julitoxcastro8983]

imagine using that as a whip

[@Sleepy_Cabbage]

talk about slinging it

[@eternasapphiremoon81]

you mean, it is now a 'PEN-is'. I'll be here all week. :P

[@pjtrump5777]

I asked my dm if i could hide my sword before we got arested. Dm: only if you get a nat 20 I got a nat 20. Dm: You take the sword and hide it in your a**. I later used the sword to help our party escape.

[@draco4450]

ouch

[@stevenmcmillion6523]

Actually pretty funny coming across this video, since my character, Xibalba, was the fighter who baked a very scared cake. It was a side thing we were doing for a player character's birthday, and so the DM decided that it would be an incredibly high DC to scare a cake into baking itself, but he would let it happen should I pass. Which is his way of saying "Sure, it's funny. Get a Nat 20 and I'll allow it." And so I did.

[@hexagonalchaos]

Me: first time dm Everyone else: new warlock, jetstream Sam, artificer, big dude, guy who interrupts me and only does pvp Players are heading into the mist filled cliffs of bone and shadow that people in town were talking about. On the way big dude (Goliath barbarian iirc) jokingly says “I look for a goat” gets a 20, you find a mother goat and a kid. Artificer (very short tiefling) wants to keep one of the goat skulls for something. Big dude Kills the mother goat, baby goat runs away. New guy (in his words: 500 pound tiefling warlock) shoots the running away baby goat with his crossbow, another 20. Arrow shoots straight through the goat’s skull, instant death (probably not painless). Artificer gets a skull, big dude gets lunch, new guy has some fun (earlier he was very happy to kick the door of a bar open as his introduction)

[@izanagino-okami8221]

On our campaign, we had just left a dimension outside our own, housing a library of all knowledge lost to civilization. Our DM likes to make "luck rolls" just to spice things up from time to time, so he explains that on a 20, we appear outside in a great position for the plot, as teleporting magic has a margin of error. Next session is a constant back and forth between the player who blinked into existence in the middle of a fortified castle, passing themselves as a maid, and the rest of the group running around Killin shadowspan and creating a huge forest fire. It was great

[@postapocalypticnewsradio]

PANR has tuned in.

[@BrianVaughnVA]

Welcome PANR!

[@postapocalypticnewsradio]

@@BrianVaughnVA many thanks! How've ya been friend?

[@martymcloud1908]

First time DM playing as some DMPCs to flavour the party, my bard possibly has some sort of bad luck magnet or something as he got lost from his partner at the start and had to be reunited by the party, then he got a nat 1 when trying to take some boxes off the way and ended up knocked out by some cooking utensils, and then the party fought a pretty weak mimic after the same guy got his leg trapped on a chair next to the mimic, and finally for the first Nat 20 of the campaing, he tried to get his leg off the chair and ended up doing an acrobatic f*cking pirouette off the chair and into the mimic's mouth... He somehow got out of there alive, even i don't know how

[@froakiefact]

The DM said, "If you roll a Nat 20 I'll allow it." Player: "Nat 20" Long story short, the character licked the BBEG so hard they both died instantly

[@baddealdude807]

the party was about to fight a dragon, the warlock asked if he could convince the people of the village they were protecting to see if anyone was willing to help. I said sure so he got up on a stem in the middle of the town and offered free catering to anyone who helps fighting the dragon. he got a nat 20. THE ENTIRE VILLAGE JOINED THEIR ARMY AND HELPED KICK THE SHIT OUT OF THE DRAGON UNDER THE PROMISE OF FREE CATERING!

[@cameronjensen9397]

Let hope the warlock brought enough food to feed the entire village.

[@baddealdude807]

@@cameronjensen9397 he was a home-brew Pastafarian so he could just summon pasta

[@cameronjensen9397]

@@baddealdude807 For free, or does he need a lot of naps?

[@baddealdude807]

@@cameronjensen9397 he can do it as much as he wants as long as its a useless prop

[@lucielm]

Free Catering, for the dragon!

[@fateric007]

Last session our Hexblade Warlock finally got a Nat 20 on his attack roll. Next thing we know he immediately yells out Eldritch Smite using a level 5 pact slot. The damage was so high our DM was like F it you instantly blew her head off. I was LMAO for 5 minutes.

[@aesiro1336]

This was more hyped than FNAF SB.

[@BrianVaughnVA]

God damn right!

[@brightsteel6019]

So I was one of the other players (a sniper) in the Intimidate Cake incident. The fighter had a very high intimidation score (the players tag skill is Intimidation, so he knows how to build for it) and the GM allowed them to roll for the memes and got the Nat 20. He won the baking competition we were having.

[@dragonlord498]

In pathfinder their is a class called bloodrager which is a hybrid of sorcerer and barbarian has a rage ability similar to a barbarian but also bloodlines and more limited spellcasting Similar to a sorcerer

[@MrInitialMan]

When Nat 20 and Nat 1 come together, the results can be... entertaining. We were at the end of a campaign with a lot of PvP going on between the mages, especially my anthropomorphic Coyote Warlock (I love coyotes, what can I say) and the human wizard. Bit of background first: The most important thing to note: The wizard's player and I are good friends in real life, and thought it would be funny if in this campaign the two would be the trope "Teeth-Clenched Teamwork" brought to life. Throughout the campaign, the warlock and the wizard would not stop antagonizing each other. It started off with snide remarks, graduated to us throwing stuff at each other, and all the way up to the warlock saying he ripped a page from the wizard's spell book to wipe himself, and the wizard expressing delight at finding a shrine to our patron because "he needed the privy, but this will do." Oh, and fistfights. Fistfights at every tavern we got to. It drove the sorceress NUTS, and she'd often bring a magic barrier between us, try to use a silence spell (doesn't work when we can write rude messages in the dirt), or try ANYTHING to get some peace and quiet. But no. Our characters remained aware of each others' existence, and therefore that existence had to be made a living hell. So the campaign is over, we've defeated the BBEG, the treasure is being divvied up, and the warlock and wizard are at each other's throat over a copper coin. The sorceress has had ENOUGH and rolls a Sense Motive check to see why these two will NOT get along. Nat 20. The wizard's player and I slide notes over to the DM. He reads them, gets a most peculiar look on his face, and says to the sorceress's player: "You realize, with sudden horrifying clarity, that their constant bickering is specifically meant to annoy YOU." It took the sorceress's player over three minutes to stop laughing. Once she regained composure, she says, "Hell hath no fury". Her sorceress casts Magic Missile on the table, rolls a d6 to deterimine how many blocks away her voice can be heard (she got 5), begins to berate us for making her life misery, and rolls an intimidation check. It seems the Dice Gods had just broken out the popcorn, because she got a *NATURAL ONE* Warlock: "I flip her off and say "Ah, shaddap'" Wizard: "I slap her on the ass and tell her to go f--- herself." Our next campaign with those characters started out with us waking up in JAIL.

[@julienlapointe8204]

Quite a while back, I started a campaign with one other person. It was... *heavily* homebrewed by the DM, in his own world, his own characters and even classes, and it was my first real D&D experience. My character had a few attacks and weapons, but two abilities will be important here : Polymorphing, and fireball. So, our campaign started with us joining in a tournament, to get some good ol' cash. My character had lost his sword, and made a bargain with a weapon's smith to have a nasty, powerful sword - he had lost his - and would pay after the tournament. If he failed, well, he would give the blacksmith his dagger, which was *really* expensive and valuable, with plenty of enchantments on it. (I joined in in a campaign the other player already played in a bunch, so that's why I had a bunch of shit I shouldn't really have had to start with.) Our first fight went pretty well, me, my protogen ally (yes, it was *that* homebrewed) against two dwarves in me has that ended up getting welded together mid-fight. Now, back to my polymorph and fireball. Me and the DM agreed that, if I rolled an eighteen or better, I could pretty much morph into anything. (Probably should've been on a Nat 20, but neither I or the DM had much experience). My ally literally ran out of batteries, and, at that point, we were getting CURBSTOMPED by the two dwarves and their mecha. Remember what I said about the fight going quite well? Turns out, the DM decided that if I rolled over eighteen, I could morph into a dragon. Now, I was a twenty meter long, eighty PVs behemoth, and I actually made the dwarves shit their pants and raise the white flag when I tore off their mecha's arm with a good roll, and increased damage from my form. Next session, my protogen friend had gotten an oil change and recharged his batteries. We were now up against two wyverns, and... It went surprisingly well. We were both doing a lot of damage to the two wyverns. I'm not sure what happened next, but I morphed into a dragon again, with a nineteen if I remember correctly - oh, did I mention my fireball became fire breath, with double damage, and only cost one action per turn? - and focused on the wyvern which had activated an ability that made it super tanky. One turn later, with two NAT twenties, a nineteen as well, and my doubled fire damage on my firebreath, that wyvern became ash on the ground. Sadly, I didn't actually roll good on how long I could maintain the transformation, and got sent back to my human form, at the same time my ally got dunked on and sent into saving throws. Next turn, I got my ass beat up, and was in the negative hit points. I thought this was the end, buuuut... The DM let me do one last attack, and if I succeed I'd get back up. NAT. 20. The wyvern was already pretty low HP, and I just got a crit with that super good sword I borrowed. My character basically stood there, with a hole in his chest, and cut the neck of the wyvern, killing it on the spot. Sadly, my partner never came back to play D&D.

[@danielwhite1890]

My first campaign, one I've been in for 2 years now, my gunslinger fighter has had absolutely ATROCIOUS luck, to the point of dying twice in one session a few weeks ago. Up to level 11 and during a small intermission I'm making a cool gun with the king that is so far overturned my brain hurts. (we are all damage gamers because we didn't plan beforehand) But the most insane luck I've ever had was for a singular one shot off in a hard to reach part of the world with a samurai, who, I kid you not, got all but one of his actions surged attacks to crit, along with 4 others during the session. He stole all my crits for the actual game XD

[@TheOfficialPSI]

Session 1 of my first ever campaign as a GM for Pathfinder 1e. The party, which at the time merely consisted of my 2 friends, an Orc Titan Mauler(TiM) and a Halfling Counterfeit Mage(CM), have just finished making their way through the prologue "dungeon"(a large keelboat I'd intended to have them use as a mobile HQ throughout most of the campaign.) It's a long story, but basically the entire prologue was meant to be a big misunderstanding that would be cleared up after a brief battle against said captain in his cabin. After which they would become part of his crew, and the campaign would be begin proper. In other words, any damage done to the ship now, would need to be paid for in full later. My little party makes it up to his quarters, just a few inches of ornately gold-trimmed wooden door away from the final intro encounter. TiM: "I quietly push the door open." Me: "The door doesn't budge." CM: "Is there a keyhole?" Me: "No." CM: "...Is it magic?" After roughly 2 or 3 minutes of my party asking questions and rolling absolutely pathetic perception checks to figure out why they can't open this dang door, managing to never ask the correct question to find out, TiM proves the first to run out of patience. TiM: "I boot the door open." Me(laughs internally): "Okay, roll." TiM: "Nat 20." Me(laughs have now become external): "The door bursts into the room, crashing into the back wall with a resounding 'CRACK!' before you hear debris loudly fall to the floor. The wall clearly isn't a big fan of this turn of events, as cracks, splinters, and even a few broken chunks now scar its otherwise lovely surface. CM: "So what was wrong with the door? Was there something blocking it?" Me: "Roll perception again." CM: "15 total." Me: "Finally remembering the existence of your eyes, you inspect the outside of the door frame, and notice, along the splintered wood, that the hinges of this door are on your side of the frame." The Titan Mauler, with his starting strength score of 22, booted a door across the room. All because he didn't think to pull it. They had to give half the money from their first quest to the captain to pay for the damages to his cabin, including replacing his lovely and expensive *pull-only* door. This time with an even more obvious golden pull ring, to replace the old rusty iron one.

[@SugarSpice07]

I am a relatively new D&D player, but in the second session of my first ever campaign, a really funny one happened. So, the nine of us had just finished capturing a pirate ship thanks to our half-orc's complete lack of self-preservation instincts. During the skirmish, one of the Rangers took an arrow to the shoulder. At the time, we were all like, level 1 (and new to the game), so our healer could only really heal one person. She had to heal the half-orc, of course, because he was about 1 hp away from fainting. We were about to end session, but the guy who played the Ranger commented on how his character wouldn't sleep and was instead messing with the wound. The guy who plays our chaotic teifling (you know the one. The choas gremlin who makes just as many problems as he solves) stands up, jokingly announces in a matter-of-a-fact tone, "I roll to slap him!" and rolls a die. Half the table bursts out laughing. "He rolled a 20," my sister says, laughing. So, the teifling slaps the Ranger so hard he instantly passes out. Unsurprisingly, HIMYM references ensue. (The best part is I caught it on video.) But that's not the funniest part. Like 10 sessions later, for some reason that I can't remember, the same guy did it again, this time to the bard. The DM played "You Just Got Slapped" in celebration. I keep trying to convince people this teifling should have like +3 to his unarmed strike. Edit: Ok, guys, it got better. Now almost a year after the initial slap (a few months probably in game time), this same teifling nearly gets the party killed. Notably, the warlock that a) would've gone beserk and wreaked absolute havoc if he died, and b) my character was entirely too attached to. Now, my character goes right up to him all "YOU! HOW DARE YOU DO SOMETHING SO STUPID!" and, naturally slaps him. So, I jokingly roll, and lo and behold, Nat20. So, this 19-year-old half-elf girl storms up to a tiefling dude at eye level with her and slaps him across the face so hard he passes out. It was glorious.

[@captainandrew9501]

I’m not really great at story telling, but I gotta share this one. Our group is currently playing a home brew campaign, where everyone is kinda made out of or has a magical/elemental attribute. We had a party of 8: -A shadow Gnome Ranger/“gun mage” -A Fire Assmair Lion Paladin -An undead Pirate Captain with his Metallic Monkey “Jack” -The first mate to the “Cappin” A Bone Giant Barbarian & Cook - a time monk with spider arms that come out his back - a nightmare baby dragon - a Savana Druid (think Steve Irwin that can change into his favorite creatures) The 8 of us were hired to find villagers that went missing. After some investigation we found that they were being abducted to another dimension through a common item. Their bags of holding. After finding one of these cursed bags of holding we went into this strange place, outside of space & time. We worked our way through the dungeon and found all the villagers. Except for 1. The mayor’s daughter. We found a secret staircase that led to a portal, & through it was where the final missing person was. Captured by a lava Naga. The combat was epic, our dragon flew to the opposite side of the room to rescue the mayor’s daughter, but an enchantment kept her stuck (baby dragon was afraid of the Naga due to back story reasons) The rest of the party focused on the Naga & minions. After the combat session the party was worn, but they didn’t have time to rest, the room started to fill with lava. The 4ft Shadow Gnome “Sanchito” was first to go through the portal to safety. Followed by the very damaged spider monk. But the monk failed a Dex athletics to jump over the lava and was singed for his final hit points. He flew through the air right at “Sanchito” DM allowed him to make a Dex save to avoid the other player. DM had a rule that small characters got a -1 to STR in addition for their small size but gave a +1 to their AC for the same reason. Instead “Sanchito” decided as a gag to try even with his -2 to try and catch the spider monk. Surprisingly enough nat 20 “Sanchito” raised the almost twice as tall character above his head using the shadows to aid his strength. However the metallic monkey Jack & the captain weren’t very mobile either with severe injuries from the fight, so they had the bone giant throw them over the quickly rising lava. They made the throw hurled both the monkey & “the Captain” through the portal right on top of the spider monk & “Sanchito” Make 2 strength checks with disadvantage (DM told me it would be a 15 DC) 18, 18, 19, 17 “Sanchito” holds the growing dog pile of his comrades. Barley making the 15 DC STR check. “Aye dios Mio, why doesn’t everyone just climb aboard!” As he spoke the DM took no pity as now the 2 more members (the asmair fire lion holding the Savana Druid) flew in and failed the Dex check to avoid the pile on. Another check with disadvantage. Double nat 20 The table erupts with the madness that basically a 4ft Spanish shadow Gnome was about to literally carry the whole party. The final 2 members come flying through the portal with the mayor’s daughter. As expected the largest character on the group pushed the dog pile forward to slide down the icy staircase. The shadows pulled together fueling “Sanchito’s” efforts to hold the 7 players & 1 NPC. The final strength check & a Dex save to keep balance while going down the icy steps. Rolled a nat 19 on the Dex save & the final nat 20 to make it down the entire staircase without dropping anyone. But collapsed in exhaustion at the bottom of the steps. The DM gave the player an inspiration & a +1 to strength checks. & still to this campaign he’s never failed a STR check. (Though never that crazy, again)

[@obiwancc]

During one of the sessions in this Steampunk game my friend was DMing, we had to dig trenches to prepare for a fight. During this, I rolled to dig a trench with a gardening tool. I rolled a nat 20. My DM then explained that my Barbarian took three hours out of the night to dig three trenches with a gardening tool, and all the other characters were just looking in awe. Later in the session, we were chopping down trees to get wood for fires and just making the trenches better for the characters to be in when the time comes. I rolled another nat 20 chopping down a tree, and my character cut down a tree with one swing. At this point, all the other players were dying laughing. After that, my character was dubbed "Trench digger Thorin."

[@beardlessdragon]

My favorite nat 20 in our group is my favorite because it created a recurring joke. Our first-ever campaign started on a ship out at sea and somebody got a nat 20 for a Listen check (3.5e) so the DM joked that their hearing was so acute they could hear dolphins chattering below the ship Now, every time we get a nat 20 for Perception checks, we say "You hear the dolphins"

[@enderskunk7644]

In our game that nat 20 would not have been a sparta kick, it would have been a roundhouse kick that decapitads silently and maybe even kills another enemy hit by the head... but no wish spell...

[@mdalsted]

"the dice are the true storytellers of D&D games" I need to remember that.

[@Wolf9918]

My funniest nat 20 was in session where I played as a monk. Team needed to cause chaos in bar so barman would be occupied, while one person from team would sneak to basement to search for clues about chaos cult that was suspected to hide in here. We decided to cause chaos by causing a bar fight. As a monk I decided to just go quite fast between group of people and just give some light punches for 3 people from that group to cause fight, but i rolled nat 20 for attack and I just K. O. them instead by one punch for each of them because these was just normal people NPC's that had small amount of HP XD

[@Doihavetodothisagain]

I was playing dnd at lunch in the high school dnd club and the Wizard who had a criminal background tried to see if he knew a guy who knew a guy (using the criminal contact feture) we where at a party tracking down a guy who had scammed us all septetly on different jobs. The wizard rolled a nat20. So the dm described how Sydney went up to this guy and correctly guessed his name and then kept correctly guessing this guy’s life events until he is convinced that they are freinds. So while the rest of us are heading out with the guy who hired us (turns out he was a bard who needed adventures to go on adventures with him so he could have story’s to tell to the nobles) we just see wizard coming out of the party expensive neclece twerling in his hand absolute cauos behind hims. The dm didn’t discribe exactly what happened because we only have 30 minutes to play each day, but suffice it to say this is my first epic nat20 story.

[@AjiraCtelin1993]

*Oh boy.* Another chance to discuss the Intimidator of Cake. So not the GM, but Xibalba Amassa, our half-elf Fighter in a basically-Pathfinder game, was involved in a cake-baking contest. Problem: he couldn't bake. So he rolled Intimidate on the ingredients instead. Nat20. They were scared into assembling into a fully-baked cake. It was edible too! It just tasted like fear.

[@brightsteel6019]

ye.

[@destructor3152]

Our monk got a reenactment of The fist of the Northstar on a bandit leader by getting a nat 20.

[@LadyR0sette]

Not me but one of my friends (A skeleton artificer named Rex) got in a bar fight. This was his introduction into the game after a player had left. Rex: I cast ray of frost Dm: ok, roll damage Rex: nat 20!! (His first roll of the campaign) Dm: the angry dunk man is now a popsicle that has fallen over and everyone surrounding the fight has left to the other side of the bar in fear Everyone at the table was laughing for the next few minutes.

[@shyfrog3731]

Okay, but a Rage Sorcerer unironically sounds so cool.

[@sebastienbusque2312]

One of my last successful games as a DM. I was playing with a couple of friends who didn't know much about the game, but decided to go big. One character was a Markus - a Hexblade -, the other was Raltzinger - a Human Monk - who took a vow of silence. My friend who played the monk was insanely lucky with his dice roll... but didn't put much thought into his role-play. I had an NPC - Karyana - who was a Fateweaver. Before we met Raltz, Markus and another friend's character - a Mystic Archer - had been tasked to find an ogre who had stolen the local tavern's sign. So, just as the group meets the ogre, I have Raltz appear and battle the ogre. Raltz rolls first and attacks the Ogre... Nat 20. I had a house rule that any Nat 20 had to roll again to see if it was a killing blow. A second Nat 20. Raltz ended up nicknamed "One-Punch Man" after his punch knocked the Ogre's head off his neck. Later, I had the group do their first dungeon mission by storming a Goblin's lair to find clues leading to Markus' father's assassin. The Goblin Boss was riding a Warg and was decked out in armor. After the group cleared the guards, Raltz uses Barrage of Fists on the Goblin Boss. I had him roll for disadvantage due to the warg mount. Nat 20. What was funny was that I had the Goblin Boss roll checks on impact, since he had been punched off his mount. Not only did his armor EXPLODE, but he went splat against the back wall due to multiple Nat 1s. Good times!

[@The_Great_Butler]

Me (a Life Cleric of Ilmater), a shapeshifting Wolffolk Rogue, and a Gunslinger Fighter. We had just finished up investigating into this giant tree that was being guarded by fey creatures and were about to leave the forest and call it a night when the Rouge attempts to convince our Fighter into carrying him for the 4 hour journey back to the keep. The Fighter tells him no. So the Rogue shapeshifts into his wolf form and gives the Fighter literal puppy dog eyes to convince him to change his mind. He then jokingly asks the DM if he can make a roll for it if the Fighter was okay with it, to which he was. So, the DM tells the Rogue to make a Persuasion check. NAT 20. I then ask the DM if I can express the sheer and utter disappointment I have for the Rogue right now. The DM tells me to make a Performance check. NAT 20. The Rogue got his 4 hour piggyback ride while chewing on my staff as I stared at him with the most aggressively disappointed look in the world for the entire trip home.

[@whirledpeaz5758]

That Dimpledore Bit, I envision the Colossus and Wolverine Fast ball special.

[@mechmoon2521]

Not quite a Nat 20 but it was still crazy. A bit of context. This was my first campaign and we were playing Tomb of Annihilation. I had died 4 times already, so I was on my 6th. My DM implemented a homebrew effect called 'Spell Fog'. This was a miasma where, whenever you cast a spell within it, you have to roll a d100. Depending on the roll, the effect is amplified or nullified. So, the character I was playing this time was a Fire Genasi Pyromancy Sorcerer. I went all in on fire. There was this monster attacking us (I forget what) and I wasn't confident I could hit it. So I did the tried and true method of fireballing it, since I'd heard legend of the spells power. I roll the d100 to see what would happen, and... Natural 100. To this day, it is one of 2 Nat 100s I've ever had. So, what my DM does is say I raise my hand in the air, and I create a star above my head which crashes into the island. The enemy was turned to ash, along with most of the island. The DM then proceeded to teleport us to the final boss, because I deleted everything else in the map, where we promptly got annihilated. This is the second funniest thing I have ever done in DnD

[@Protestant_Paladin440]

Not a DM, but I had to share. We're playing a Greek myth-based campaign. We were in a city, looking for Pan (The God of the Wild) to interrogate him. mid-search we run into some thugs who work for the BBEG whose identity is a mystery and all share the name "michael" and yes it is spelled with a lowercase "m." Me: I want to jump on top of a table. DM: Make an acrobatics check. Dice: Nat 1. DM: Your character slips and falls, rolling onto the floor pathetically Me: ok..... for my bonus action i will roll for intimidation Dice: *NAT 20* DM: (sigh) you look at the thugs with a dirty glare and they crap themselves and trip over themselves as they try to flee. TL;DR I try to climb on a table, fall, make some thugs crap themselves as they run for it.

[@meepstump5893]

My character (A halfling fighter at the time) rolled a nat 20 to seduce a campfire, it summoned a demon whom my character would fall in love with, and sell his soul to.

[@Ferrari255GTO]

Hmmmm... *you're actually a bard aren't you?*

[@ltericdavis2237]

I think you mean halfling warlock now

[@meepstump5893]

@@ltericdavis2237 Yup

[@Kualinar]

Last one... So, that's how that Party Companion Throwing skill work.

[@tylercrockett7273]

Just the other day I got a nat 20 (went up to a 22)and I kicked a 300 pound locked stone door off it's hinges in a single kick in the middle of a bossfight, almost crushed the boss who had run through it and was on the other side. (The boss could run through stone like it was water.)

[@vermacvontaven2200]

Had a campaign playing as a kobold paladin. At one point during the campaign we came across a town that was put to sleep with blue berries that had a sleep spell on them. I took as many as I could hold and later in the campaign we came across a griffon nest and as our spell caster dwarf was mind controlling a spell sword to attack the griffon while we were hidden two other npc adventurers walked up to us and without any words exchanged I rolled two nat20 back to back of flinging a blue berry in each of their mouths causing them to fall asleep.

[@memeboi18]

I’m pretty late but during a oneshot campaign my older brother hosted I was playing a black dragonborn moon Druid where we were hired mercenaries because these two boat cities (imagine like 100-200 pirate ships tied together) were at war. At one point when we were robbing an extradementional bank because reasons I rolled a nat 20 on a perception check to find a painting to steal, my brother went silent for a moment, and proceeded to describe me finding a painting made the first ever awakened treant. In that same bank, my cousin, who was playing a rouge rolled a nat 1 on an acrobatics check and yeeted themselves into an endless void and became the only death of the oneshot. It was awesome

[@theworldsgreatestjidiot9667]

I punched the ghost so hard IT'S soul flew out of it

[@Thebringeroftartlets]

We were playing a homebrew campaign and had to get a unicorn horn. My character was morally against this, and sat out of the assumed fight. One of the players turned to the DM, and said that he was going to attempt to gaslight the unicorn into believing that it had always wanted to be a horse. Our DM laughed and told the player to roll for persuasion. The player rolls, looks up at the DM, and utters three words. "Nat F***ing twenty". The entire table erupted in laughter and applause.

[@articusramos808]

The fighter went Gordon Ramsay.

[@beardlessdragon]

Our party got very attached to this NPC innkeeper named Tom. He was an older guy whose wife had already passed on and he had this funny, drawn-out way of saying "well" that my friends and I still imitate to this day The town was raided and burned by goblins while we were out adventuring (classic) and Tom was trapped under a burning rafter, on the verge of death, when we found him. We wanted to roll a Medicine check to try to patch him up. The DM was basically like "he's nearly dead so it's pointless unless you get a nat 20." Welllllll, guess what we rolled :) Tom became a party member played by the DM who couldn't fight but would sing music to lift morale (or annoy people, depending which party member you asked lol.) He was later mauled by an owlbear, may he rest in peace. He was such a funny addition to the party for a while

[@maxblake5564]

Not a DM, but I am a player with a really funny Nat 20 story. Our party was in Waterdeep for the Waterdeep: Dragon Heist campaign, and we were trying to bust a Zhentarum slaving ring. Essentially, the Zhentarum were breeding Kenku for slave labor in a warehouse in the Dock Ward. We stormed the warehouse, and halfway through the fight, our healer, a lizardfolk murderhobo motherf**ker jackass idiot druid, decided to set the warehouse on fire. WITH HALF THE KENKU AND THE ENTIRETY OF THE PARTY STILL IN IT. Miraculously, we managed to get ourselves, as well as all the Kenku, out safely. But that’s not the end of it. After we got the Kenku out safely and were staring at the burning warehouse (with varying degrees of satisfaction/annoyance) two Bugbears burst out of smoldering crates. As we stared each other down, the DM had the party roll initiative. My character, a Tiefling School of Necromancy Wizard (and no, he was not evil) went first. So Creizhar (that was his name, Creizhar the Immortal) raised his hand, extended his pointer finger, pointed at the dumbass druid that had set the fire in the first place, and yelled “HE DID IT! HE DID IT!” The DM had me roll Persuasion. I roll, and upon seeing the results, yelled (and I quote) “OH MY GOD! NAT 20!” The Bugbears immediately began pummeling the druid and only stopped when the city watch came to see WHY THE F**KING WAREHOUSE WAS BURNING. Oh, fun fact, Creizhar, after setting the Bugbears on the druid, did not even attempt to contribute to the encounter in any way, let alone any meaningful way.

[@revampedharpy09]

8:53 maybe he intimidated the cake mix into baking itself?

[@councilofcringe5520]

Hugged a mind flayer and lived to tell the tale

[@taekwonditto]

This one happened recently, may not sound funny but man it got our player laughing his ass off. For context, the party is going through a dungeon full of illusions and killed a goblin, the goblin wasn’t apart of the illusion and the same player, who is playing a cleric, decided to revive him (because the party already has a bad moment with killing innocent goblins). Everyone was trying to gain the goblins trust and trying to communicate with it when our Cleric pulls out his rations and gives it to the goblin. Everyone else were making crummy rolls, and on this one, the Cleric rolled a nat 20 and was laughing his ass off. Long story short, that goblin is now a little companion that is slowly converting to worship the Cleric’s goddess of light

[@Traveler-254]

We never had much luck with Nat20's in our family; they were usually followed by something dastardly. I'm not sure if this would fit better in a NAT-1 story, but this is one of the funniest things caused by a NAT20 that I remember. In one of our homebrew campaigns, our rogue lost a few teeth when our oafish NPC dwarf fighter let go of his club mid-swing due to a bad roll. Once he awoke after the skirmish, he dazedly looked at the scattered teeth, and mumbled "I wonder if I could get any money out of those". DM overheard him, had him roll and, sure enough, nat 20. Out of nowhere, the tooth fairy--that tiny, adorable pixie that we all knew and loved as kids--showed up and gave him 25 gold in exchange for the teeth. It's just a shame that our rogue rolled a 1 for perception and tried grabbing the tooth fairy's hand to help himself up, resulting in him pile-driving her into the cobblestone path. Double-shame that the tooth fairy was a holy deity, nigh-indestructible, and specialized in hammers for, as our DM so eloquently put it, "extractions". Triple shame that she landed right next to our dwarf's discarded club. Her retaliatory swing sent the rest of our rogue's teeth overseas. Who knew dentures were so hard to find in fantasy worlds?

[@tylerosborn7596]

This was my first campaign. We’re right at the climax, Big Bad is in the town square and there’s all manner or Dire-wolves and lycanthropes and beasts all over the city. As we’re charging towards the town square, having small fights along the way, we see 4 wolves attacking the shopkeeper lady (our Elf-bowman-ranger’s love interest) and her daughter (my Barbarian Halberdier noble’s love interest. (It was a really fun character to play)). She send our Dragonborn Paladin and NPCs on ahead as we go to rescue the damsels in distress. Our Goliath monk says “I HELP NICE LADY TOO” and charges with us. The wolves had them cornered and were facing them in an inverted wedge. The Goliath starts at the point man and uses Fury of Blows and punches 3 of them as he passes. I’m just one step behind and roll to attack the first one. Nat 20. I step up and swing like I’m Babe Ruth in his prime, cleaving straight though the first and killing the second as well. I follow up with a Polearm Master bonus attack and buttstoke the third in the face (dirty 20) and crush it’s skull. The elf then pumped several arrows into the last one and killed it nearly instantly. The whole combat took 6 seconds (in game one turn) and we told the women to get up to the citadel and charged on towards the Big Bad. Our Dragonborn and NPCs (and DM for that matter) were astonished at how fast we dispatched the wolves. They hadn’t even cleared the street before we caught up to them.

[@Alex-wu2sl]

Has to be when the rest of the party learned something about my character. I play an earth genasi swashbuckler/psi fighter who in the previous adventure had to split from the party for a hot minute. The DM had given me an interesting effect on any 20, (checks and saves included… yep) in that it became a 1. She had sold some luck to a hag to save the woods near our castle from an undead invasion. Only he and I knew this… until I rolled a 20 to hit some kind of undead as we stormed the bbegs lair. Everyone cheers as I faceplant into my desk. The DM describes how “As Ametrine swings, the longsword is on track to behead the creature when suddenly her elbow locks and the longsword hits the wall with a resounding clang.” It was glorious chaos as I got so many messages wanting to know what was happening. We are now five months from that event and NO ONE has figured out what happened IC or asked what happened when she had to split from the party… we are a chaotic bunch.

[@cmykrgb1469]

I needed this today. Thank you.

[@adamjjj318]

I love these, see yall in 2-4 months for part 7.

[@Rkguerra12]

I was still a new DM at the time running Tomb of Annihilation and had added a random house full of Gnolls trying to summon a Flind in a mountain city on the island I think the city was part of the module but the gnoll house wasn't I added it as a secret TPK hag tower style like in Curse of Strahd (I like adding in random items or encounters the players will probably never see) but what I didn't expect was for the party to actually stumble upon it and go in not only that the Rouge player had rolled 3 or 4 Nat 20s in a row killing like 4 gnolls and almost one shotting a giant beefed up gnoll we all freaked out at the chances all for him to roll a Nat 1 on his next roll crazy stuff but in the end with help from the local guard after making a big mess in that house they managed to stop the gnolls and shove the Flind back through the portal.

[@BrianVaughnVA]

Brian Vaughn VA here has tuned in!

[@postapocalypticnewsradio]

-panr liked that

[@notaphycologyst6644]

(not nat 20 but close) One time i was fighting a goblin camp, and so i thought something up: i chucked my magic living skull friend at them, whacking one in the face, and a couple more accidentally snapped their own necks because they turned to see it too fast

[@grantgranby]

We were in our 2nd session, all level 2, and on the run through the woods (my fault, I accidentally said something to the wrong person about gold I had pocketed, so the ship we were on was chasing us). The dm wanted to make us keep moving a bit further to find the plot, so he sent an owlbear our way, expecting us to run. However, our cleric and barbarian had different ideas. The cleric wanted to scare it away, so he used thaumaturgy to boom his voice, which the dm let him have advantage on intimidation. First nat 20. Then the Barbarian steps in. He wants to try to tame the Owlbear. The dm lets him roll an animal handling to try to approach it. 2nd nat 20. It's still not tame yet though. So, the Barbarian asks if he can roll to do a "mating dance" of sorts. Dm says okay, but roll at disadvantage. Barbarian convinces dm to let him do a flat roll. 3rd nat 20. The Barbarian named her Princess Fluffie Kittie. Tl;dr 3 nat 20's got us an owlbear pet at level 2, breaking the balance of the campaign for a bit.

[@dejmira]

The more I watch this videos the more I want to take part in one of the campaigns

[@FlynnMcBride-g3t]

Dragin born makes a perfect grilled cheese sandwich using fire breath and got a double advantage for making grilled sandwiches

[@Spazielle]

Just came from your newest video, and Zolra made an appearance! So awesome to see reoccurring characters

[@justinisorange]

YESSSS I MISSED THESE

[@enoraltheoutcast]

8:43 I kinda feel like it was about intimidating the ingredients into baking. Kinda like how it happened in one of the previous episodes where a barbarian rolled a nat20 for intimidating their wounds into healing themselves.

[@williamsrdan]

CN Rogue leading the party up the bell tower, not deactivating every trap, side stepping a few minor ones, that end up getting set off by the rest of the party, causing minor injuries. Arrives at the upper landing before entering the bell chambers, and used gum and string wrapped around the door nob, in order to open the door safely. Then, activating his Ring of Greater Invisibility, creeping out onto the parapets, and seeing it occupied by gargoyles. Taking advantage of the cursed bag of holding, which always produces a cookie upon first attempt to retrieve any item from said bag, he invisibly force fed each of the gargoyles cookies. Causing the gargoyles to flee in confusion. I rolled so many 20s that session that the DM banned that dice.

[@joedominguez8064]

in my 1st campaign ever my friend DM. the party made it into evil wizards lair and killed him, only to find dying was the final piece of his ascension plan to spirit form. My orc rogue rolled a nat 20 to successfully tackle his spirit back into the corporeal realm 🤣😂 This led to a whole new BBEG as wizard was imprisoned in a wand, as well as my rogue being given "ghost touch" abilities and transitioning to monk to unarmed strike undead and spirits 😅

[@demonchildDLC]

This one is from my current campaign: I'm playing a bard that is a talking, tap-dancing llama (we are being a little comedic this campaign) and as a joke, I keep having my Llama fart as a form of protest to the rest of the party. Well, at one point I ask an NPC if they have a drinking problem, and after my question, my friend's dragonborn barbarian reaches over and hold my llama's mouth shut to stop him from asking stupid questions. In protest to having my mouth held shut, I fart. My DM has us all roll a con saving throw. I rolled a Nat 20. My llama unleashed a fart from the depths of hell and the rest of the party had the poisoned stat for one minute.

[@o.d.d.792]

Rage Sorcerer So a Super Saiyan?

[@eternasapphiremoon81]

I remember this one instance where a friend of mine was running this Tower scenario, and I was playing a Dragonborn Barbarian. Other members include a Goliath Barbarian (and yes he called himself Paul Bunyan with a Babe the Blue Ox animal companion), a half-elf Monk, an earth genasi druid, and an elven wizard. We end up in this arena-like room where we face off against 3 giant spiders and 5 smaller versions. I use my Fire Breath to toast three of the spiders, and the rest of our group manages to take down the others, leaving this one ironically evasive normal spider to kill. It was my turn. I had my Dagger + 1 out at the ready, and I roll a freaking Nat 20 on the attack. So now I have this image of my big beefy Brass Dragonborn Barbarian rage-charging at this average-sized spider, literally STABBING this thing into pulp yelling "DIE! DIE! DIE!"

[@thomasahuman7764]

Once in a game I was playing we were in a dungeon and our monk got stuck in a room with three large fleshy monsters. One was in the way of a door to let the rest of us in. Btw we were level 2 or 3 anyways I, a dragonborn paladin, roll to open the blocked door. Nat 20. My DM makes me roll for the damage the door does to the monster and dead. I insta killed it with a door bursting in like an action hero.

[@Nikoli492]

Story request: part 3 how did you kill a tarrasque?

[@madblaze3287]

We were playing Forgotten Chronicles with some friends, I played a necromancer and we ended up fighting ratfolks. During the combat, I buffed myself with the aspect of the succubus, the fight continue until my character gets hit pretty bad, so I use vampiric caress on the rat ratfolk who just hit me to regain some HP, so I roll the dice to attack and I make a nat 20. Then, we remember that my character is still in his aspect of the succubus and we all start laughing as we agree that my character has canonicaly killed a ratfolk by making him c*m to death. And that's not even the end of it since we had a character in our party who was nicknamed "Ragnar the red" after being covered in blood, remembering that, my character was not too far away of being nicknamed "Arselim the white"

[@JezElectro13]

I don't know if I can call it funny but my first time as DM I made the party fight 4 members of a dangerous gang. It went very well for the party, and the Brute told them to give up. Me: Roll for it. he rolled a Nat 20. The dangerous gang of skilled criminal warriors ran away tripping on everything and each ended up leaving with 1 HP.

[@Queen_Bread]

Very beginning of the session as i tried to introduce the party. Isekai cowboy rolls 20 and kills a werewolf with a stick

[@palenut1775]

DISCORD NOTIFICATIONS!!!

[@BrianVaughnVA]

DEEESCORDDD!

[@LorienInksong]

first story is creepy af and the exact reason I'm very careful about who I play with

[@blisterbeetle01]

Ironically I was already popping mine when the vid dropped!

[@unknownslayer7363]

Hexblade warlock picked up a cursed weapon. Rolled a nat 1 and got his soul sucked into it and the entity inside tried to order him to let his soul be eaten. He said "no f*ck you" and tried to take control of the weapon now that he was inside. Rolled a nat 20. Now he and the entity inside constantly fight eachother for who is in control longer and he has gained the ability to posses anyone that picks up the weapon

[@Fraud82702]

I was playing curse of strahd. Might have some spoilers in this. had this dead goblin I word carry around and sometimes I would take him out and beat enemy's with him. So anyway, my DM has us teleported to the south pole, (I don't know if this is part of the main story or just something he added) he told us Santa had been killed and we needed to kill the one who did it. So after some fights, we made it to the guy who killed Santa. Krampus. I slit his throat and my friends fighter finished him off. So one of the elves then took over for Santa, and he said he would give us a magical item in thanks. Nothing too op. I chose a bag of holding. I put the goblin in and then decided that krampus's body would be a nice thing to have. Fast forward next session, we arrive at a town, and when we think we are safe, krampus jumps out of the bag, apparently healed, holding my goblin cause it was the only thing he could find. I really liked that goblin. I wanted it back. I yelled really loud "Give me the goblin". DM says roll for intimidation. Nat 20. I got the goblin back and used it to kill him. The goblins body was pretty much just paste by then end of it, but it was worth it

[@lockwoan01]

The Dwarf Paladin and the Dhampir Rogue Currently playing as a Dhampir Tabaxi Rogue, and initially the rest of the Party (Dwarf Paladin, Orc Fighter, and Bugbear Artificer) didn't know what I was - as I seemed to be just a strange cat-person to them. Party has to fight this Knight or whatever, that was a bodyguard for an evil wizard that was using the dead as slave labor - that one vanished through a portal. My guy takes some serious damage from this dude. Well, since the Paladin (along with the Fighter) was busy dealing with skeletons and such, and the Artificer has their own issues (like having a 6 in their Wisdom Stat so that he could have a 16 dex, 16 Charisma, 16 Intelligence, 10 in Con, and 8 in strength), getting healing from them might have been an issue. Well, I decided that it was necessary to heal myself, and took matters into my own hands, or rather teeth - got a Nat20 to make the Bite, and I was one shy of Max Damage - I have a 14 con. This brings me back to full health. Well, this happened in full view of the rest, so Insight Check, and guess who got the Highest - Dwarf Paladin, who got an 18, which, with modifiers, became 22 - they realized that I wasn't an ordinary catperson (like any of the party is ordinary). Fast forward to last session - Paladin had to miss the prior one, which involved a prison breakout by a minotaur pirate - and Paladin and Rogue are standing watch. Rogue goes, "You got questions, don't you." Paladin: I do. Rogue: Short story is that my father was a Tabaxi mercenary, that was turned into a vampire. Mother was a Priestess of Palor, that he was to protect. Between them, they had me. Next day, tracking down some bandits and cultists, we learned that the cult has prisoners that they plan to sacrifice. Rogue is in favor of rescuing them. Paladin gets distracted by a Sending stone that a spy - which the Rogue had killed - had dropped into a river. Paladin fails the dexterity save, and lands near the cultist faction. I climb down from the cliffs we were on. Fighter and Artificer - especially the artificer - do their own things, trying to safely reach us. Fighter throws a jar containing mildly poisonous spiders - it doesn't do much, except alert Rogue and Paladin that the prisoners are in a nearby cave. Both make decent Perception Checks. 5 Kobold Guards, and 7 prisoners of various races. Rogue: Think that you can distract the guards while I climb on the walls to get behind them and free the Prisoners? Paladin: I can do that. Well, Paladin distracts the Guards alright, by falling into a pit, while Rogue sneaks past them all using the walls. He frees one prisoner, passing him a dagger. However, after freeing the second (and third, thanks to Prisoner 1), Rogue's actions are noticed, and he gets shot at, one hits for some damage. Paladin climbs out of the pit, and manages to rush the one kobold. Rogue passes his remaining dagger to another prisoner, and pounces upon the second. Currently, there's a few more kobolds, and a few more prisoners. We'll see what happens.

[@pulsefel9210]

ah so thats why the pizza place has yells coming from the back!

[@wren1044]

So I haven’t played long so I don’t have much. I was in a one-shot that started in a prison. The whole party was these edgy tieflings, elves, etc. who had been in this prison for years cuz of murder and such. While my character was a raging, 3ft tall, barbarian kobold who had only been there for one day because she stole a durian from a merchant. Stumped on how to get out, I talked the DM into letting me keep the durian with me. On my turn, I rolled to throw it at a guard. Nat 20. We decided that the guard was conveniently deathly allergic to durians and died within moments.

[@nixotinix]

My (heavily intoxicated) fighter decided to brawl a 9 foot tall Goliath woman named Elephant Hunter. Long story short, we were in a tavern with a strict "no fighting" rule. Ms. Hunter said *something* to tick off my fighter, and he tried to pick her up and throw her. Didn't work, rolled an 8. She proceeded to suplex my fighter. The tavern owner gave us both the option of either "walking the plank" (which we later found out launches you at very high velocity) or fight each other in the fighting ring. My drunk fighter of course chose the ring. No weapons or magic, just hand-to-hand fighting. I rolled 2 natural 20s back to back. The fight was over in 2 rounds. My fighter then proceeded to throw up over the side of the ring because, if you remember, he was 17 shots in.

[@alexanderholscher6548]

My mother had an operative in starfinder who failed a stealth roll while investigating the back rooms of a night club in an adventure module. Some of the gangsters noticed her, and demanded to know what she was doing. A wrong answer would result in a 3v1 fight, and she had been disarmed of everything but her knife at the entrance to the club. My mother said "Oh, I was just looking for the bathroom." And rolled bluff. Got a Nat 20. So I look on the map in the module to have one of the goons escort her out of the back area, only to realize that the map didn't have a restroom, despite having a bar. All at once, the goons came to a sudden realization, and rushed out of the building desperately looking for somewhere to relieve themselves. The best part was, she got a second Nat 20 to use the same tactic a second time, only to get a Nat 1 on trying to use it a third time against the gang leader.

[@thesuperdk513]

One time I was playing DnD with some buddies and some mutual friend we invited for our session that night. I was playing a Dragonborn Barbarian tank with a monstrous attack stat and the mutual friend was playing a rogue with pretty low constitution. Mutual friend was being kind of annoying and slowing us down and I decided to have my character smack him on the back of the head to get him to stop. This technically counted as an attack so I had to roll for how much damage it would do, and I rolled a nat 20 and accidentally killed him. I apologized profusely while my buddies laughed their asses off, but he was pissed and left.

[@florin6628]

It happens a lot that somebody can't join a session, so we always have to iprovise. One time, a friend couldn't join a session because he was sick, so we decided to leave his character (a Half-Elf Rogue called Luke) behind in the tavern we stayed in. The next session our friend was back. While his character was still in the tavern, we were exploring some old mineshafts filled with enemies. That session started with a fight in the mines, so we had to deal with some dammage. Two members even fainted. After that battle we've sended two members to town to search for a healer and search for Luke. Luke is addicted to stealing and pick-pocketing. Ofcourse when the two partymembers arrived claimed our friend that Luke was pick-pocketing in the tavern while we were gone. Our DM said that he needed to roll for Sleight of Hand. A natural one. The DM said that while Luke was trying to pick-pocket a giant Orc, one of the partymembers (called Opal) yelled Luke's name while entering the tavern because she was looking for him. Because of that scream, all attention went to Luke, hands still in the pocket of a giant Orc's pants. The whole tavern got angry and got mad and started intimidating Luke. Luke tried to escape, but rolled a 9 for athletics. The giant Orc just picked him up and said "Do you know what we do with people like you?" Luke answered with a quiet trembeling voice "No..." The Orc demanded Luke to empty his pockets and give all his money. Luke said he only had 4 silver pieces and some copper pieces (even tho that is not true, he has tens of goldpieces, he is one of the richest members of the party). He rolled for Persuasion. Natural 20. Everyone in the tavern was like "understandable, have a great day", took 4 silver and 3 copper of Luke, and just let him go without any hesitation. He got lucky...

[@WolfeZolfe]

There was a time where my friend made a character that would be there for just one session, and he was colorblind, he was a complete joke character and his colorblindness appeared when he received a blow on the head on a bar fight. At the end of the session he was knocked out by a guy who was like a mafia boss that wanted him dead, after the battle we treated my friends PC and he woke up, the dm told him to roll a d20, in case of a nat 20 he would not be colorblind anymore, my friend rolled and started laughing, it was a nat 20. Everyone was in shock, no one could believe it and turned out that character was the best joke character to appear ever in my games.

[@Gabeygamer-oz8gq]

discord ping go brr

[@BrianVaughnVA]

Brbrbrbrbrr

[@arkron81]

Not my funnies, but my best "Nat 20" moment was just in my last sessions. The group was traversing the seas, going from Waterdeep to Baldur's Gate, when our ship suddenly got assailed by a heavy thunderstorm. A Marid showed up (for those who don't know, imagine your average fantasy genie, but a lot frog-like) who demanded we surrendered the ship to him. Naturally, we said 'nah, fam' and the Marid went 'aw dang' and left us alone. Nah. He proceeded to summon two water elementals and attacks our ship. Fight began, and our sorceress (my character's girlfriend) head closer to apply some Shocking Grasp on him. Not only did the spell not do the amount of damage expected (he was resistant), but he also grabbed the sorcress' hand. My character, a fighter, did not like that one bit, and ran after him shouting at the Marid to let her go, and... I not only rolled a nat 20 for the attack, but I also rolled pretty high on the damage (5, 5, 6 and 2 for a greatsword), plus a 10 and an 8 on my Battlemaster's maneuver. And for the second attack, I ALSO rolled a nat 20, and rolled quite decently for the damage (4, 5, 4 and 3) but no maneuvers. The third attack (we are all level 11) was not a crit... but I did roll double 6s on the damage dice, so there's that. Can I also said that I was ALSO using the "Great Weapon Master" feat for -5 attack and +10 damage? In total, I did over a 100 damage to the Marid in one single turn! The Marid wasn't even bloodied (half-health) at the end of my turn, but it felt GOOD to deal that much damage, not gonna lie.

[@mitcharlotte672]

I managed to sneak behind a minotaur that was terrorizing a rich guy's farm, i wen't straigth to a shed that had magical items in it and I roll a 20 to destroy de door without making much noise (i had acid), so i enter and find just a bigass crystal that i cannot identify, i grab it and start to make my way back and i roll a 1 while sneaking and the giant crystal drops in my toes and i make the scream of my life and i get pummeled by the minotaur

[@epsilonphalynx8693]

When I was in 8th grade, my friends and I were playing for the first time(3 e had just been released). We were teaching another friend of mine and the dm had him start simple with a bar fight. The DM ask what he does, he asks "is there anything near by I can use as a weapon?" The DM rolls and says there's a table of pies near by. He says "I pick one up and throw it at the nearest patron." Rolls, nat 20, and the DM says "you throw the pie, the strawberry on the top of the pie dislodges and falls into the patrons throat, and he chokes to death on the strawberry." That year, for his quote in the yearbook was "I like pie."

[@sterlinggecko3269]

I don't know about funniest, but on Friday, during my 3 year long campaign concluding boss fight, the berserker boss rolls a nat 20, followed by another nat 20 to confirm the crit, and the tank would be dead, but then I rolled the miss chance for Displacement, a miss, he rerolls due to Blindfight, also a miss, and the tank survived. the tank got killed and revivified like 2 rounds later.