What was Your Funniest “Nat 20” Moments? #5

What was Your Funniest “Nat 20” Moments? #5
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Stay tuned for more awesome DnD content!
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DND players, what was your funniest “nat 20” moment? (r/askreddit)
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What is the smallest way your DM has driven home how "evil" a villain is?

[@catiminiclergus537]

When teaching my little sister about dnd. Basically explaining deception, she says: « Like, I can say to a gobelin: Look over here! And I will roll deception then? -yeah, but I ll do a intelligence roll for the goblins and contest it to see if it work. But goblins are quite dumb, so generally you d get it (she was a rogue) *sister roll a 17 deception* -ok i ll see how intelligent that goblin would be: *nat 20* -…. Ok that goblin apparently was a genius, first of his class and the like…let’s see another goblin *nat 20 fkn again* -…. That was his twin brother, even more brilliant, apparently… It was not part of a game and just rule explaining, but still made us have a good laugh

[@sxar_0660]

🤣🤣🤣

[@darkwarriorprogram6546]

“That was his twin brother” I’m dying! 🤣🤣

[@knylover4565]

I remember a meme that started from a funny thing that happened about 2 years ago in a campaign that one of my good friends was DM but for some reason he was always lugging when people told there backstory’s in game, I was Playing a changeling named Crystal who was disguised as a orc named Zhog for a good part of the campaign but no one besides the DM known I was a changeling that the back story I was tell other players was a complete lie. Well about 10 sessions in a changeling NPC that my character had a good relationship with died, in respect I kneeled next to him when he was dying and showed him I was also a changeling by reverting to my true form. Other player walked over and put a hand on my shoulder be for revealing that he was also a changeling, followed by another player doing the same thing revealing she was also a changeling, turns out all 5 player characters where changelings and the reason the DM was laughing when someone told there backstory was because everyone was lying there butts off. Form that point on when ever that DM laughs one of our character will yell “You lying Changeling!” And punch the closest character, this has caused 14 bar fights and 1 TPKs and I wish I was joking because we accidentally punched a Dragonborn that killed all of use with one breath attack.

[@inukithesavage828]

This is absolutely the funniest one here, and a great character moment.

[@chucklesdeclown8819]

Ok, this is one of the funniest ones I've found, even funnier then when I used one of the party members throw up to distract an enemy so I can get some strikes in.

[@mrshark117]

I ain’t reading all that

[@InactiveNight]

If I was a dragonborn I'd do the same

[@arinomaly]

I have two moments. In the campaign I play in, (it was originally a oneshot but spiraled into a campaign, I'm a rouge/sorc fallen aasimar named Rela) we started off at a funeral for one of our party's mentor, a goose aarakokra who was now dead named Louis Gooseman. The character that he mentored and sort of raised is a Goose Aarakokra named Goose Springsteen, a blood hunter. We had just arrived at the funeral, and I immediately asked to roll for perception to see if there was any food. Nat 20. THere was a table completely full of bread. We spent the majority of that session goofing off with bread and somehow befriended one of the later revealed lycanthropes when one of the players gave him bread and then proceeded to ignore his warning. The other moment came in one of our 'this happened before the events of the funeral' sessions. Our characters were in a tavern the night before the funeral, and this swan aarakokra walks in. We find out he's named Gregory Swandude, and I jokingly say "I want to eat a piece of bread intimidatingly at him." NAT 20. He throws a chair at my character out of fear, and a bar fight happens. All because I ate a piece of bread intimidatingly.

[@transmaddie]

DMed once, 2 hours ago, I have 1 nat 20 moment from that session. A centaur in the party squished himself into a bar stall he very much didn't fit in, then when he tried to leave, he rolled a nat 20 on strength, and snapped the table in half. The bartender was standing at the table at the time and lost his crap, then a warlock from the party who had become fast friends with the centaur during the conversation they had, decided to try and get the centaur out of this by convincing the bartender that the table breaking was the bartenders fault. He rolled a nat 20. The bartender payed the centaur 10 gold for having put him in such dangerous conditions.

[@jerryferguson5]

So use to seeing PANR has tuned in. When I didn't see it as the visual comment when I clicked on the video I had to check. Thankfully it is there.

[@bobtdm190alt5]

Same

[@letsplaysvonaja1714]

The only nat 20 I can remember was one to look for loot in a skaven nest The DM gave me the ring of my character's father, it was the symbol of the gang leader (died in character's background story and the skaven recycled the corpse for a hellpit abomination) and although the ring didn't have any magical effects or anything like that I attached to it and used it to show off my authority, even though my character was the last living gang member and did not reestablish her "family" until the campaign's afterstory

[@dalekcaan8495]

Was this a warhammer fantasy campaign or do you mean wererats?

[@letsplaysvonaja1714]

@@dalekcaan8495 the dm just added skaven because why the hell not

[@beacon5076]

One time one of the people in our party rolled like 3 20s in a row lol

[@markhomer7051]

@@beacon5076 ive done that. my DM at the time let us gamble our 20s so every one after the first doubled the damage output (ended up doing like 40 damage with a normal short sword.)

[@postapocalypticnewsradio]

PANR has tuned in.

[@thedeathray8620]

10:22 I can only assume that a group of dwarves lead by a dwarf named Windrose started helping on that one, singing and motivating everyone throughout. For those not in the know, I'm referencing the song Diggy Diggy Hole from the Yoggscast, which was covered to a metal version by the Italian(?) band Windrose

[@darkwarriorprogram6546]

I AM A DWARF AND I’M DIGGING A HOLE. DIGGING A HOLE. DWARF! HOLE! (I’m glad I’m not the only one who thought of that. Lol)

[@nitaishneor6214]

I played as a halfling rouge for some time like a two years ago. We were in the middle of a vampires dungeon, and we appeared to stumble upon a brewery. I, being the stupid lucky bastard I was, put everything in the room in to a pot, mix and take a sip. I roll low and end up not tasting the delicacy so in my next turn I dive into the boiling poison/potion and roll…. A nat 20. I die, yes, but I get to make a new character of the ghost of my rouge, having essentially kept my level but to a different character.

[@Daniel_Coffman]

In my head after seeing that story, I'm now imagining that Galleon is totally OP. He just acts useless and makes his attacks easy to dodge, but intentionally saves absolutely frickin' DESTROYING an enemy for when he absolutely needs to. XD

[@darkwarriorprogram6546]

I’ve got a good one from about a month ago. In this campaign I play a fairy (think like Tinkerbell size) and the party is trying to get a trapdoor open. After the rest of them fail to break open the trapdoor I jokingly said I was going to try. Nat20. The 3 inch tall fairy ended up lifting a trapdoor like 1000x her size when the kobold fighter, human ranger, genasi barbarian and the orangutang cleric couldn’t get it to budge. (I would also like to clarify that even with the -2 I have in strength the 18 I got was still the highest result from that)

[@lucielm]

I'm just imagining a squeaky voice going. "Boys, stand back! Let a real fairy show you how it's done! Just think happy thoughts! HEAVE HOOOOOO!!!"

[@darkwarriorprogram6546]

@@lucielm That is the best response this could have got, and I applaud you for it.

[@Transubstantiate]

The funniest natural 20 I've been a part of happened to me from some... PC on PC violence. This was back in the days of D&D 3.5 and we had a three person party; my character was James and my future wife's character was Tiernan, both of whom were literal drunken sailors as they were (former) pirates who used alcohol as a coping mechanism. I know they were humans but I can't remember their classes any longer. The third member of the party was Raze, a half-dragon monk. Raze's player though our characters were hilarious to have around but Raze couldn't stand them, finding them annoying at best and he rarely felt that positively toward them. One day... or maybe it was evening... possibly night... James and Tiernan stumbled into Raze's room while he's trying to sleep and they wake him. Raze tells them to leave or he will make them leave. James refuses because he's feeling friendly and he and Tiernan both loudly proclaim that Raze needs to lighten up and that the teatotaling half-dragon should join them in their merriment. Without warning, Raze throws his pillow at James. The DM says, "roll to hit." Now, in 3.5, there was no "advantage / disadvantage" mechanic. Instead, you either got a positive modifier or a negative modifier on your roll. A pillow, being an improvised weapon, got a negative modifier to the attack roll. This meant that, no matter how dire a situation, you could always hit with a single good roll. Which, is of course; what happened. Our friend says, "natural 20." Laughing, the DM says, "roll to confirm." Our friend, elated, says, "natural 20!" The dm says it again: "roll to confirm." In our gaming circle, there has been an on-again, off-again house rule which states three natural 20s on the same attack roll lead directly to instant death. Do not pass out, do not collect 200 gold pieces. "Natural 20." The DM, because it was so much fun, had called for that third roll when we hadn't used the mechanic the entire rest of the game. However, he modified it slightly because PILLOW. Instead of one-hit killing my character, the pillow was thrown with such accuracy and force that it knocked James out cold. Best natural 20 I've ever been a part of.

[@shinrafugitives3880]

The elf in my pf game once rolled a bunch of useless nat 20s in a row while rolling to assist several use magic device checks for the rat to move a lake of liquid fire to a place it won't cause any damage. Mind you, the DC to assist a skill check is 10, and the elf had a +7 mod or something like that. So she just wasted a bunch of nat 20 rolls

[@alexan629123]

Not actually a D&D story but still the most epic and fricken hilarious “Nat 20” scenario I’ve ever been apart of... Three quick notes on the dice system for Kids on Bikes: 1) there is no combat system because you are supposed to be playing noodle-armed-pre-teens. 2) characters in the game have 6 stats, except instead of using a 20 you apply one d20, d12, d10, d8, d6 and a d4 to each stat and that is the die you roll for that ability. 3) If you roll the highest number possible on your die (say a 4 on a d4) the die explodes and you get to roll again and add the number to the additional roll. There is no cap on how many times a die can “explode”. So, I ran an all-girls game of Kids on Bikes. The general vibe was “summer camp fun util weird stuff starts to happen”. It was a 5 session mini-campaign and the first three sessions was some wholesome All-American summer camp shenanigans, with a bit of Scooby-Doo-esq detective work on the side. It’s our fifth and final session, and before this there had maybe been two times in the entire game a character’s dice had “exploded”. Once during archery practice and again on a random charm roll. The kids have just uncovered that the summer camp is basically a buffet table for an eldritch horror living deep in the mountain. So our four heroes are trudging through the woods armed with a rusty pocketknife, a hunting bow, and an AK-47 (don't ask), off to face whatever horrors await them beneath the earth. They get to the belly of the beast, but PLOT TWIST turns out the camp counselor, portrayed with a goofy midwestern accent, has been working with the monster all along! The camp councilor seems to be possessed by the monster, but instead of ambushing him and tieing him up, the kids decide they are gonna fight. Being the DM my immediate thought is "there is no way they are gonna win”. The highest die they had was an 8, with the other stats being two 4s and a 6. But they roll. First kid says “I’m gonna shoot him in the leg!” Kid rolls his d6 and it explodes... twice. It’s a 16 and camp councilor Barry's kneecap fuckin explodes! Next kid wants to shoot him with their bow. They roll up with a d4 that explodes... Three. Fuckin. Times! Kill shot directly to the throat. Yup. They’ve just murdered a man... but it gets better, or worse, depending on how you look at it. They make their way into the den of the beast. The walls are flesh, there’s a massive heart suspended 15 feet up in the center of the room. The kids decide they will destroy it with team work. In a detailed description of a two maned circus act one of kids THROWS the other child wielding the rusty pocket knife through the air and towards this horror’s heart as both kids dice, you guessed it... explode. A d12 turns out to be a total of 27 as a 4 foot tall girlscout gets Popeye level strength and flings her friend through the air while the other flying and flailing child somehow rolls like a fuckin 20+ off of a d6. All this to say, our last session went off with a bang. Those four girl scouts saved their summer camp, and we wrapped up the game agreeing that they’d all need some serious counseling after one wild summer.

[@bitmaster64]

this was a fun listen, but gotta say that last story with the Kenku and the Orc cracked me up XD

[@francescosacca6674]

Oh, this one is very fresh, happened just yesterday. I'm a new DM, and I'm DMing my very first campaign. The party was in a ruin, fighting a huge monster, this large humanoid panther with smilodon fangs. They were looking for an knight NPC to help them in a quest, and said knight was in deep trouble. He also had a black horse, which he tied outside of the ruin. One of the players was missing last time, so he steps in and tames the horse with a really good roll. Then he charges in, and attacks the beast with success. Then I roll for the horse's morale (you know, an herbivore should be scared of large predators), again really good roll, the horse isn't spooked. Then the player asks to make he horse attack. Nat 20. So the horse rears up and hoof-punches the monster right in the face, making it back down and roar in rage. This absolutely magnificent proof of coolness earned the horse a name and a personality. This is the story of Alicante, from scene prop to one of the most badass horses I've ever seen.

[@jebus9311]

The funniest time I had a nat20 was when my fallen aasimar rouge character had convinced a bunch of little kids that a freshly decapatated zombie head was better then a normal football (my character was CE)

[@praisethesun7834]

I friking love this series

[@soundwavedoesthings]

Same

[@TarossBlackburn]

It's been a long time, but once I was playing a Warlock in an adapted Birthright setting. As such we were all spoiled lordlings and around level 9 we finally went off on our First Actual Adventure. We were to liberate the daughter of some lord from bandits in the mountains. We all bought new stuff, all shiny and cool for our Adventure. The Paladin and Fighter got themselves shiny new plate armor as well. At some point our DM throws the 'narrow mountain path next to a cliff' at us and we decided to be SMART adventurers. Using our ropes we tied ourselves to one another, for safety. If the rogue or the warlock, the paladin argued, would slip the strong and powerful warriors would be able to catch them. Of course, the paladin is the one to slip, followed immediately by the fighter. We get one moment to yell one action so the rogue goes "I cut myself free". Well, that's one thing to do. The warlock, I decide, panics. And with his Strength dump stat I proclaim that "I loop the rope behind my back and dig in my heels against the rocks. Natural 20 strength check. I hold onto the rope just long enough for the two biggest and heaviest members of the party to cling themselves to the mountainside and clamber back up.

[@StateBlaze1989]

Galleon there has an int of 10, which is average base level intelligence, yet is described and played like he has an int of 6.

[@nomiflower9707]

Rolled a 20 for doing the distraction dance to distract the enemies. Teammates had to role to not be distracted

[@MatthewSchooley94]

A few days ago in a D&D Discord server I'm in, I had my lizardfolk monk paint a portrait of another player's character; got a nat 20 on the DEX check. Got 1000 gold out of it! ^^ Earlier in that RP, I rolled an INT check to see how much she knew about guns. Nat 20 there, too.

[@misterbilly3698]

Not me but one of my players. Anyway they were fighting this dark goo thing. It was rushing past them to take control of the iron golem. One of my players ask if they can use a sponge to soak up the goo. I say "it is too small". Then the Sorcerer ask if the can use polymorph. Now they have big sponge. I ask the other player to make a attack role with the sponge. Nat 20. He sucks up half the goo, making the monster it was forming into have half health. It doesn't end here. They kill the monster and goo begins to run away, player asks to attack with sponge again. I say "fuck it, why not". Nat 20. At this point I thought his die was weighted, it was his 6 nat 20 this session.

[@aienma6660]

I'm play a Barbarian/Monk, with 20 strength. We were doing a tournament style fight Teams take turns sending fighters and eliminating them... best of 3 wins. The opponent I just fought was very cruel about his fighting, and nearly beat our Cleric/Rouge to death (killing allowed)... due to her being a human. The NPC claimed, as her set the human back on her feet, stating the rules are... "if they stand, they can fight". Before finally getting bored and throwing her out of the ring. (She kept using her healing spells to try and out heal his damage, and win a fight... as she had yet to so far, almost costing us the win many times) My fight comes around, and I fight him... no healing in between, not that he took a lot of damage. I walk up, in a rage, and he strikes... getting low damage, made lower with my rage giving me resistance My turn... NAT 20, I slam my fist into his ribs... as a loud crack echos though out the stadium, dealing over 30 damage The NPC crys out that i broke a rib, as I did about half his health in one attack, and that he trys to forfeits I crack my knuckles, grinning at him "If they can stand, they can fight" Bonus Action, Furry of Blows 2 more Nat 20's... easily over 50 damage as I send this dude rag dolling out of the ring, nearly dead... as while I am livid... I am still a good person. Subdue damage on the last hit, that tipped him into the negative.

[@doomsandmore]

That moment when the barb picks up the dwarf paladin and nat 20 throws him into an ice wall breaking it and knocking out the caster . It is now known as the mini me fast ball special.

[@NightSkyNyx]

The male orc bodyguard story is probably my favorite one of this video lmao

[@AlastorNahIdWinRadioDemon]

I was actually the DM of this story and my party was meeting the big bad for the first time. This was about halfway through the campaign as the BBEG had been using a proxy he gave powers to to do his work up until now, but that guy wasn't really working out so he let the party kill him, gave him a bit of a eulogy about how no one had actually cared about him and he was just a pawn. In addition he was shown fighting members of another evil group the party had had a few interactions with and fatally wounded one of their members in front of the party moments prior to this. Needless to say, this was an intense first meeting up to this point and things just kept rolling from there. He explained a bit about his whole plan to the party and his tragic backstory, and one of the PCs actually knew him before that happened and has had similar plights as him due to both being Tieflings, so they're trying to keep things civil. However, the BBEG starts spouting some reverse racist rhetoric about humans and Aasimar and the Aasimar Paladin has had enough and speaks up about it. The BBEG then challenges the Paladin to a fight and the Paladin decides to draw his weapons and approaches. Little bit of background here, the Paladin is a more seasoned adventures in the party who has some of his powers sealed to keep him on par with the rest of the party, but I let him know said seals break in this moment and to use his higher level character sheet in this fight. One of the BBEGs lackeys then out up a Wall of Force separating the rest of the party from the Paladin. Initiative is rolled and the BBEG gets a 23 while the Paladin only gets a 15 despite having Advantage from his Weapon of Warning. A few things about the BBEG to state now are that he is a Pact of the Blade Hexblade Warlock that has Blackrazor as his weapon with all the Invocations that enhance damage for their Pact weapon and such as well as being max Level. So, BBEG charges a Banishing Smite and goes for his first attack. Nat. Fucking. 20. Between all of his bonuses and the doubled Smite damage he does 105 damage and the Paladin in his released form had only 150 so he got Banished for 1 minute. The party decides they can't handle this and no one else chooses to fight him for the time being, albeit the Barbarian did throw some sand in his eyes before they ran for the memes. The Paladins player actually wasn't too mad and says it was pretty funny things played out that way, and everyone still can't wait to beat the boss at the end of this to this day.

[@jonathanmarks3112]

3:06 Do not get between a sorceress and her mask! 4:37 This story is legendary.

[@DragonKnightCole]

So, after the pie loving Paladin story, freaking Dominoes ad for the pie rewards thing plays. 😂

[@dragonlord4362]

Me: (player) I’m was in a dungeon with my new friends (random group that I was partnered with) was in a room with a bunch of rats and a big rat being the mother. We were fighting the rats when we got to the last rat. I ask my dm “can I grab one of the characters put them on my bow and send them through the wall” note I am a ranger dragon born with good strength. Dm: “Ya role for strength” Me: ‘Proceeds to get a nat 20’ Dm: “So you pick up the human roug and sling him on your long bow. Roll for attack” Me: ‘Proceeds to get another nat 20’ Dm: “You pick up the person and send him through the wall and killing the last rat” And after all that, my character was then called the rat destroyer.

[@KordellCunningham]

The one with the Ork Bodyguard is a clever way to counter those NAT 20 seduction roles, and it's hilarious.

[@randomtechpriest2644]

Story time: It was the first campaign I was in and I was play a fallen aasimar monk, who had a +1 to charisma. So we were all having fun, and eventually I decided that my character would sing for everyone, and my buddy said that if I rolled a Nat 20, he would use the music bot and have it play “Toss a coin to your Witcher”. And so, my monk with his +1 performance goes up there and rolls a nat 20. My buddy just sighs and plays the Vapor wave version of the song since he was sick of the original version.

[@Fastdragonstar]

i used a jump spell before jumping from an airship towards a floating wizards tower in the sky (10 ft wide, 5 ft long landing area). i rolled a nat 20 on the athletics check to get the right distance then i had to roll acrobatic to see if i sticks the landing *rolls below 5*... i faceplanted into the door and then had to make an wisdom saving throw and got the same result... worked out for the better since i got pulled into a friendly telepathic conversation with the owner of the tower.

[@ARCCommanderOrar]

That Halfling Paladin. "Jump good"

[@otakubancho6655]

The one with the 100 lb sorceress was my favorite!💖💖💖

[@spoons641]

Oh my God I wanted to play Dungeons & dragons in this brings me joy.

[@Law01YT]

Ight I’ve got a good one. In this current campaign I’m Playing a Trition Paladin/Sorcerer. Currently we’re delving a dungeon. Our party split up to cover more ground. My character goes to explore with the Siren Bard. We find a large open room with a gnome sorcerer meditating. We alerted him and he threatens us with utter defeat, so we roll initiative. Both of us got high initiative. The Bard attempted to use charm person but it didn’t work. So I do what I though would be funny. I attempt to just absolutely demoralize this evil gnome in the worst way possible, hit the Gnome in the balls. I rolled with Disadvantage and double nat 20 divine smite, thunderous smite him, instantly killing the gnome and probably hit him so hard his dead ancestors felt it and the pain carried into the afterlife. TLDR: Ultra Smited enemy Gnome Sorcerer in the balls causing basically Instant Death

[@stoney_05]

this is the series I found you on lol

[@MrRipper]

The original has over 2 million views! MENTAL

[@strangecannibal]

Convincing a guard to a fancy ball that my shield as also a walking stick.

[@johnscarborough9627]

So it was the final session of the year for my party. One member was running late so our session was shorter so we did a PvP fight with no consequences. I (a level 6 Arcane Trickster Rogue) get downed fairy early and left to death saves. I roll a Nat 20 and am instantly revived, and the DM asks me to do a Deception check to feign death. Another Nat 20. The player who killed me (a level 6 Bard) decided to try and finish me off, thinking i was still downed, and rolled a nat 1 on his attack. As he stepped away i rolled my THIRD nat 20 on opportunity attack and jabbed him in the shin with my spear. After the other alive player (a Ranger), shoots me and downs me, i roll the FOURTH nat 20 to instantly revive myself

[@doomslayerobama]

160000 chance for 4 nat 20s, just under 3.2M put of 1 for them to roll a nat 1 also. Wow.

[@bluetrooper858]

My character was relaxing in a town venue after a long and successful fight and he spots a beautiful looking girl. i walk up , offer a drink and strike up a conversation. After a while I say "it's getting a bit loud around here , I know a really nice place just outside the town. Then she asks "do you want to show it to me ?" To which I reply laughing "that's what she said". The dm asks me to make a persuasion check and as you guessed ... Nat 20 ! Got that girl in love with me and she is now my characters' fiance 😂

[@user-Lemon234]

A friend of mine ran a campaign and one of the other players rolled a Nat 20 on sniffing grass

[@ahalfsesameseedbun7472]

My funniest crit 1 was when I was playing a wood elf rogue named Randolf. One of my allies was on the other side of a barn and was in trouble I attempt to shoot over the barn, roll a 1 "you release your arrow. As it soars over the barn a slight breeze alters its path and it sticks into your friends back, killing him." After the encounter I go to recover my arrow while every one is around. Stealth check, roll 1 Randolf to others: "hey guys did you see that arrow come out of nowhere and hit him?" as he is pulling the arrow out "crazy right?" Proceeds to put arrow back in quiver.

[@harmonicaman4782]

10:35 this is my favorite dnd story yet.

[@matthewhoagland693]

Love your videos, haven't played since high school (20 yrs ago) , gunna try n get a family game here I. The near future

[@Hello_Itsme_]

When I heard about the character that tried to be manly and I heard his name was Rowan all I could think of was, wait Torchwick lived also when did he start exercising (RWBY Joke) (he died in volume 3 in one of the last episodes) Edit: I just remembered his name was Roman not Rowan, but close enough.

[@auraemerald8434]

I’m mostly new to D&D and one of the first things our DM did was fight a boss witch and then I (I swear, in character) attacked someone who had just joined the campaign, rolled a nat 20 and nearly cleaved her in half. Had to use Lay on hands to save her.

[@TheWanderingMaster]

Loving the stories, though what happened to some of the playlists... I like having them playing in the background

[@Scorpious187]

We'll have to look into that, maybe make some playlists of our various related series and things.

[@TheWanderingMaster]

@@Scorpious187Thanks for looking into it. These stories are my go to for listening while driving.

[@BrodyLNg]

I got double nat 20s in a row on a smite evil crit in 3.5e and did 53 damage

[@russdarracott395]

The last story, hahahahahahahaha hahahahahahahaha hahahahahahahaha hahahahahahahaha hahahahahahahaha!!!!!!!!!!!!!

[@stanvessies5888]

We were in session 3 of our campaign when we came across some raiders trying to rob us blind. One of my partymembers (changeling) wanted to do an intimidation check to see if it would do something. NAT 20, he was doubting what he would change in until another party member started playing Face Off by Tech N9ne (you know the 'it's about drive it's about power' song) he decided to change into Dwayne Johnson and start screaming those lyrics towards the raiders. No wonder they immediatly decided to flee, it was really funny in the moment

[@willmacfarline363]

I rolled a natural 20 on an athletics check to tweak my nipple to keep my rage going with my Goliath Barbarian. It was concluded that I ripped off my nipple and it has become the staple my character throughout the game. Culminating in a ritual wherein I rip off the second one to become a real giant. That one natural 20 at level 3 carried a story all the way to the end of the campaign. It was hilarious!

[@derdodel7978]

I once rolled to play despacito. my char had no prior experience at playing the piano and succeeded anyway

[@brycewalker973]

Player here, More amazingly lucky than anything, Wife and I were playing with a few friends. It’s my wife’s first time playing, and it was our second session of said campaign. The party was traveling along to the next town over when we heard some sounds of loud grunting and shouting near a body of water. We snuck up behind angry ogre trying to catch some fish. We start whispering and discussing a plan of action when all of a sudden…. Wife cheerily shouts: “HE LOOKS LIKE HE NEEDS HELP! I WANNA BE HIS FRIEND! Rest of party: WHAT!? DM laughing: she declared it! Roll with disadvantage … two nat 20’s Silence around the table. Wife lets out a Homer Simpson “WOOHO!!” Laugher and cheers ensue Wife calmed him down, helped him out and they became immediate best friends. While the other members of the party were her companions. We even built him a fire and made his cave more homie. Orgee the ogre is now a reoccurring NPC who got a job as a kingdom guard and helps us with quests here and there. 😂

[@dragonriderabens9761]

My Dragonborn Barbarian was angry at a grave (in his mind) injustice that had been done to his best friend He punched the nearest wall First roll failed, and he broke his hand Second one was a nat 20, and the wall shattered The guards were none too happy, but for obvious reasons were in no rush to make a move on this 9’ 3” 1050lbs mass of scales and muscles Thankfully, another member of the party was there to talk them out of arresting him (though he would have gone quietly had they tried. He was no longer raging when they came)

[@BoulderWest10]

Rolled double nat 20 on a called hit to the nuts. We were playing a nightmare before Christmas campaign, Santa was kidnapped by Krampus and brought to Oogie Boogie in Halloween town. We’d just taken out Oogie, and Santa had been saved by a sacrifice by one of our PC’s. I was a lvl 10 rock gnome armorer Artificer, ran up a 15 foot wall while I had both haste AND Ashardalon’s Stride, called a hit to Krampus’s ballsack. “It’s hanging right in front of me, and he tried to kill Santa!” Double nat 20’s and I one shot Krampus. I now have his balls as a magic item in all campaigns. Krampus’s balls of fire resistance.

[@markhomer7051]

I am the DM of a campaign. one of my players has had the worst luck with his dice. it started out wonderfully. (he is a seal paladin) and went fishing at level 1. rolled a nat 20 for fishing. so me (love doing random things) decided to roll for what he caught. I rolled a d10 and a 10 was supposed to be an encounter. well i rolled a 10 and he fished out a house sized crayfish (somehow the party won with only one person standing and hardly any health.) the next time he rolled a nat 20 was a side mission. they found a board to help an old man till his field for a harvest. they figured easy money and would only take a week. so i had him roll to see how much of the field he would till in one day. ya... he got a nat 20 and tilled about 4 days worth of work in one day. now i have to point out this guys luck the rest of the campaign. i had them fall down a deep cavern (part of the story line) and were supposed to live. he was complaining that his character is crap because of his rolls and needs a new character. so i said fine if you roll above a 5 you live. otherwise you fall in to the river of lava that is next to you. ya he rolled a nat 1. then almost broke down in tears because he didn't really want to lose his character just hates the horrible rolls he gets. failing almost all rolls he makes.

[@Salad_Pickle]

I uh, out-tracked a small cabal of goblins over our hunter ranger, as a celestial warlock Was pretty funny watching him track a squirrel while I located our prey

[@canofbatteryacid7644]

i rolled nat 20 for being used as a makeshift cannonball one time

[@anonbefallen4807]

We were playing Wizard school campaign and one of our party members was the dodge ball obsessed gym teacher, through means that if I explained would take all day we ended up in an alternate world and had to fight on a tournament to get to a portal that would bring us home. Before the battle an elder Wizard we met gave the party exclusive unique weapons, I god a flaming sword made of bees that I could use as minions, this gym teacher character got a dodge ball that would ricochet and home onto more targets if they got a high enough roll and could ricochet near infinitely if given a good roll. The crowd sitting in the stands for wealthy folks in the tournament was booing us like crazy causing this Gym teacher in a blind rage threw his ball into the crowd, he rolled a nat 20 and they were all common folks with low hp so the ball would hit one kill them than move onto the next, the teacher killed several thousand rich nobles with a ricocheting dodge ball, but the funniest thing is the normal civilians seeing their opportunity started a revolt against the upper class, won and celebrated us as heros before sending us through the portal.

[@TheAstroProblem]

Nat 20 on a roll that didnt matter, and two nat 1 ones on my first combat encounter. All in the same session.

[@48ramen84]

my sister and my dad and his friends were playing DND once and my sister was a 3 foot tall halfling who had a favorite chair and was digging a hole for it. One of my dad's friends was a 7 foot orc that rolled to throw her in the hole, break the chair and throw the remains in too. then my sister rolled a nat 20 to jump out of the hole, grab the orc, and throw him in the hole.

[@sebastianwinters9864]

Rolled a One on the Last Death save and a gust of wind from the window (lived on the 44th floor in the mountains) blew the paper we rolled on over planting the die on a nat 20

[@thatonedude9148]

No ones gonna see this but its ok First game ever, my friend convinced me and 3 other friends to try out DnD in a one-shot. None of us had ever played before so we had pre generated characters. We meet in a tavern and after introducing ourselves are approached by a guard. The guard says that there is a dragon who has threatened to destroy the town and the mayor would gladly pay anyone who could slay it. We agree(because what else would we do it our first ever time playing DnD) and then our Warlock asks if the guard, Phillip, would like to come with us. Phillip says, "I cant really, Ive got to stay here and protect the city in case the dragon does attack. Warlock Player asks DM if they can try and persuade Phillip to join us. DM says reluctantly sure, roll for persuasion. Its clear DM doesnt want Phillip to come along, as they say it'll be difficult. And in the first roll of the one-shot, hell, the first roll of us ever playing DnD, the PC rolls a Nat 20. So Phillip joins us and ends up staying for the whole one shot TLDR: PC persuades intro NPC to join party with a nat 20 on the first ever roll of part playing DnD

[@animelovinggamer5712]

So we were sneaking through a cave to an enemy encampment and I rolled a 6 on stealth. My character tripped and face planted. The enemy became alert and I asked the dm if I could roll a persuasion check to convince them that I wasn't there. I rolled a 19 and the dm decided if I could roleplay the scene then I could successfully persuade them that I wasn't, in fact, there and that they imagined the sound of someone falling.

[@jedi_cat_l4976]

Ahh... It was snowy, I decided to be fun and make a snowball and throw it at one of my teammates. Nat 20. This teammate was also probably the strongest team member we had, and I just wrecked them with a snowball. I was followed by a very angry teammate carrying a 10 ft snowball the rest of the game.

[@ajh22895]

Okay, the party had fought some guards on a train whilst on the run from the law. Which happened because the Loxodon Bloodhunter just killed (as far as they knew) a fellow party member (Cleric/Warlock) after she called him a racial slur. So, the new character (a Warforged) had been knocked out in the fight and the Loxodon (on 1 HP) was examining him. Nat 20, he popped up and knocked out the Loxodon.

[@Debble]

Ah yes that reminds me! There where these secret wall doors that took immense strength to open and the dwarf and dragonborn with really high strength failed spectacularly so my gnome (2ft tall) got frustrated with them and tried. Rolled a nat 20 so i bashed the wall in

[@MrMeYesMeandOnlyMe]

I had a fantastic nat 1 after I got cocky about a performance roll that I had an absurd modifier for (yay bards). I scoffed, “hah! A performance roll? Me? Why of course!” Rolls nat 1. “Well...”

[@journey9641]

I want to watch the 1st story as a series

[@karisasani7006]

11:00 If he said, "I Target SPECIFICALLY her"

[@circeowaggles]

The edgy rouge character rolled nat 1's for the entire game, almost every intimidate roll which he beefed up. He starts getting made fun of for being unlucky. Final boss is hiding in the darkness taunting our heros before the big reveal. The rouge is the only one who can't see in the dark. So he takes a shot and finally after a humiliating string of bad luck nat 20's, nat 20's again to critical and than maxes damage dice rolls to send the big bad running away with one hit point.

[@mikkokortelainen2045]

Started playing with My friends, first campaing going, dm's homebrew. I am a human samurai fighter, one of us is lizardfolk cleric and we have this halfling paladin who keeps falling in NORMAL, NO CHALLENGE battles. But whenever facing some evil big baddies, for example we got surprised by a zombie like thing with a Legendary action. I saved the paladin by throwing The creature away from him and was ready with My katana for Next turn. The thing managed to scare My character away, was only level 4, and poor wisdom. But, Next comes our paladin. He says "let's get Epic", stabs The creature's big eye with his rapier, Nat 20 and smite. Let's say The creature literally exploded to smitherines and we were all covered in slime 😂 The cleric, who had The same religion, commented: "show off". We all laughed so hard. Dm Said that he underestimated us, thought this battle would get longer. 😅

[@remingtonwright6796]

Captain American Pie over...

[@thecaptain5051]

The one nat 20 our paladin rolled as he tried to find out the breast/cup size of a female npc.

[@ragegaming1653]

My character is a order of scribes Wizard fairy, and she consistantly when She needs to roll perception and its important rolls 7 or below, but when its something not important, she rolls 15+.. Its happened constantly

[@ragegaming1653]

Oh and despite in character being a semi-pacifist fighting only when she needs to (or if she know sthey won't talk about it).... Has blown up a huge base by accident because of a fireball she casted, And buried someone alive in snow with a snow storm.......

[@Manwithsquirrel]

I was playing a red dragonborn named dave and I was in a cave fighting goblins. There was one gobling in front of me so I attack with my greataxe (Nat 20) instantly killing it with 47 damage launching the body 50 feet across the cave but it doesn't end there. The goblins, horrified and enraged at what I did to their friend, all climb on me and all 5 roll nat 20s downing me instantly, (luckally the cleric knew spare dying so i was fine but that was the funniest down i've ever had)

[@yinzer2231]

One session the DM split the part of 4 up into 2 groups after falling into a cave. The Rogue and Barbarian were stuck behind a magic mirror that would open only if the imitated what their alive reflections did. The reflections were holding a long oval stone (inside joke it was a dick and named after a bitch we hated in high school) after trying all options the Barbarian say "im gonna shove the stone up the rogues ass" DM allows it. He rolls a NAT 20. We all laughed for almost an entire hour.

[@peytonstanfield2703]

Got two for you, both of them dealing with transformation. For the first one, it was our second session, all of the PC, (except for mine because I wasn’t the beginning session) were making their way to a hotel. Once they got to the hotel, they met up with my PC at the hotel and were assigned hotel rooms. Now for reference, my PC, and another’s (my friends PC Drake) Lived in this city as their background so they already owned a hotel room, when they were assigned new ones, they were confused, upon investigation, they noticed one of their belongings were missing, a Drake’s gerbil’s food and my PC’s fancy cat treats for her cat (more onto that later). They went down to the reception and asked about why their stuff was gone and if they had it in the lost and found. The receptionist nodded and checked. She found nothing in the back so in defeat, my PC and Drake headed to get the cat treats and gerbil food, little did the receptionist know, comet, my PC’s cat saw the gerbil food and treats, and as he walked away, he glared at the receptionist saying ‘filthy thief, stealing our food’. They let another PC (her name is Jax, who for reference, can hear animals talk) hear him, queuing her to tell us, ‘comet said that the receptionist lied and are hiding the food’. This cause drake to roll a intimidating check, which he got a nat 20! All the receptionist say was him transforming into a giant dragon right before her eyes, causing her to pass out. This caused a ruckus of laughs and a slightly broken hotel. Next up is a fight session in the same session. We were chasing a grimm through the forest as a field trip, which led us to a undercover thug base. We made a plan that Drake would walk up and talk to the thugs up front to see what is going on/get in, long story short the thugs didn’t led him in and started up a fight, this led to drake rolling to transform, which he got another Nat 20! Que a thug getting smashed into a wall be a oversized dragon, as we seamlessly waltzed right into the thug base, boyfriend was amused at 2 nat 20’s from the same PC in the same session, which resulted in a lot of laughing and banter all together.

[@deonmurphy6383]

Ok it isn’t D&D, but same unreal roll, so a Phaser IV (star fleet battles) range 100, through a down shield, and destroyed the ships bridge. Got a WTF look from the recipient.

[@Landonc48]

I was attempting to rip a kraken tentacle after grappling dm laughed said your gonna have to roll hight nat 20 basicly a orc just grabs a massive tentacle and rips it clean off

[@Cabashokun]

So, this just happened. The DM and I are veteran players while the rest of the party are sort of new to the game and we are playing an all female characters party (sorta happened accidentally). We went into some thief's hideout for the quest we were doing. Inmediately our paladin rushes into the first door they see, just to find herself in a bedroom with 3 of the thief's, 2 sleeping in their beds and the third one awake. She quickly rushes out and closes the door and the thief tries to push through it, she quickly moves aside managing to get him to stumble forth. Me (the bladesinger) quickly closed the door behind him after he stumbled and the palading tried to grapple him. All this ruckus started to wake up the other 2 sleeping thiefs and we rolled initiative. When the thief's turn came up, they started banging at the door "Hey! Whats going on!?". Me, being the person next to the door, decided to do a silly quip "housecleaning", everyone had a laugh at that and the DM asked me to make a deception roll... Nat 20. They confused, backed from the door as their turn ended, the next turn was the rogue, who described how she tied her hair and went into the room and started to make the beds, when my turn comes around i also go into the room help make the beds saying we just wanted them to have a good rest. After that, they went back to sleep, the rogue started cleaning the boxes, I assumed she was gonna rob them under the pretext of cleaning... imagine my surprise when the rogue declares she actually believed me when I said we were housecleaning and was actually intent on cleaning the room... we did get their coin pouches and "uniform" cloaks tho, looking forward to see how the rest of the exploration goes.

[@jacquelineanderson8248]

Nah my dm: roll stealth check at disvantage Me: nat 20! My dad: disadvantage remember? Me: oh yeah (rolls again) Nat 20!

[@trinstonmichaels7062]

Trinston was here.. .

[@nickantonowitsch4903]

I am playing a fighter and needed to proof that i am no magician, so i said no problem and tried to cast fireball (party at lvl 1). i rolled a nat 20 and suddenly castet fireball on the antagonist of the quest and his guards, oneshotting all of them.

[@nickantonowitsch4903]

Now my lvl 1 fighter is able to cast fireball once per longrest

[@jonahulichny9874]

I actually have a story on my own. On my first campaign we were fighting a vampire for the main villain, and we decided that the best course of action would be to pretend to be the guys pet dragon (one we killed). I ended up being the guy who rolled for charisma to convience the guy I was the dragon, and I got a D20. the "battle" ended there.

[@Walker-vm6bf]

I wasn’t the one who did this but a friend did, so pretty much we were a few sessions in and my friends character died, we will call my friend E, E had a backup character planned so he came back as a paladin gnome. another friend and I put absolutely no trust in this gnome that popped out of nowhere. he convinces us to let him come with us on our journey and we head off into the woods. We came across a bunch of snowmen that were pretty much invincible to anything except fire. none of us had fire magic. after 2 out of 6 players were unconscious and 2 others extremely injured E decides to pray to his gnome god. DM says roll for 20 and you can pray to him. he rolled a 20. The DM was surprised and said that E was too far away from his god so he can’t come. E says “can I pray….harder?..” DM says “fine roll for over 95”. he rolls a 98. The table goes crazy and Garl Glittergold himself gets infused into E and he goes super saiyan. he kills all the snowmen with ease and revives and heals everybody to max hp.

[@randomguyontheinternet5030]

so on the westmarch im playing in, about 40 so players, 10-20ish are active. We have passive income in the form of daily jobs where you work for the day and get your gold which is just an ability check/3 gold per day. well we have one guy, a celestial warlock combat medic who for the LIFE of him keeps rolling nat 1s. he has rolled so many nat 1s that we celebrated his nat 2 jokingly because 'hey it's better than a 1'. He is the forever poor healer that everyone wants on their team because no one plays a healer lol

[@wontonkid7343]

I know it a lil late, but I wanna share a story from my first campaign back in September of 23 We were hunting a gang called the Lily's roses that controlled a lot of the slums in the city, our artificer had the idea to make a pipe bomb as a distraction, sorta like a flash bang, she didn't roll so hot so I, the 11 intelligence half orc ranger, wanted to step in to try since he's good with his hands. Rolled a fuckin nat 20 The dm described it that I had loaded the explosive up with teeth from the sea elves we fought a couple sessions prior and made it almost perfect with the artificers instructions Few sessions later we put it to use, it rolled max damage, obliterating the leader of the gang, and me thinking I couldn't top what the explosion, hung out in the roof until my character spotted a gang member sneaking up on our cleric, and with the holy 20 rolled once again, I dropped a max damage elbow drop from 35 feet above from the neighboring roof onto the poor lady

[@zero4g227]

So I rolled a nat 20 to throw arrow I killed to goblins lol

[@destroyer4929]

I've got a somewhat funny one: So I am in a campaign I'm playing a tiefling warlock (yes I am utilizing fireball to its fullest) where we started running lost mines of phandelver I missed two sessions because of some complications that came up and when I arrived to the next session we were picking back up in combat with some spiders the excuse for me not being there was that I was on "wizard twitter" and then I roll for an eldritch blast Nat 20 and I kill the spider the mental image of my character looking up from his phone after losing an argument and then just smiting the next enemy he saw will for be funny

[@kaikoacorvikeiagreen3265]

Ok so, I was the DM in this story. I was running a Pathfinder campaign for some friends, but the important ones are a female Human Ranger (Q) and a male I-don’t-remember Fighter (N). Q: Can my character have a baby with N’s character? Me, still not very experienced: Sure, but you’ll have to roll- Q: NATURAL 20! Me: *facepalms internally* *Time passes* The party is in a temple, surrounded by skeletons. Q is the only one still conscious. Q: Can I give birth to my child, and immediately chuck it at the skeletons? Me: It probably won’t work, but go ahead. Q: Another f*cking natural 20 Me: Fine, roll to hit the skeleton We all know where this is going. Q:Natural f*cking 20 Me: The baby launches at one skeleton, ricocheting into the other ones, killing all three. However, your baby is killed in the process And that is how a baby ruined my encounter through the power of Natural 20’s.

[@heroicheart6911]

Within 10 min crew

[@souldragon9130]

for that last story: r/suddenlygay

[@gibslewiston8142]

It wasn’t a nat 20 but I rolled a 3 on itimadation and the wear rat rolled 2 lol

[@timothylambert5820]

Not a DM but a player. It was a one shot home brew and I was a human cleric. Don't remember what alignment I was. Anyway the Boss was a gelatin cube who was hostile and was spawning zombies. I decided to bow down to it and worship it. I rolled a nat 20 and I started a cult worshiping this boss. That is until my party killed me and then my Boss (which is my god at this point) I don't know how many times later I did things like this

[@dakinademino977]

I rolled a nat 20 to slam a door shut. I slammed that door so hard it wrecked the door opening and sent the door flying off its hinges, leaving me standing there stupefied.

[@bakedpotato7201]

I was playing a barbarian and the rogue wanted to try sneak through a bandit camp i went with him woke up a bandit that was sleeping i then rolled to intimidate him saying "I was never here" rolled a nat 20 the bandit went back to sleep so thats how i snuck though a bandit camp using intimidation

[@Anima_Draconis]

Not my funniest but best timed nat 20. I was playing an 8'7" Dragonborn Bard. (Not the seduce type) and during a battle I grapple a thief picking him up by his throat. My DM asked what I wanted to do next so I said "lemme intimidate this guy." "OK. You gotta roll-" "26." (Nat 20 plus 6. Having an 8'7" dragon like creature can come off as quite intimidating) "As you hold the thief up eye level you start off with a low rumbling growl and then you let off a loud roar bearing fangs at the thief. What next" the dragonborn says 'any last words?' "The thief was so scared he is shaking in his boots and can't muster any words. Roll with advantage to see if you can damage hi-" "nat 20." "Nevermind you don't need advantage. You crit him and kill him. How do you wanna kill him?" "Decapitation." "Your dragonborn slides his blade underneath your hand and fully decapitate the thief"

[@brashirott3813]

My funniest natural 20 moment was when I wasn’t even DM and I was a dwarf bard college of creation named Oskar goblinsbain weapon was a war pick me and my uncle Who was also DMing Where in the start of the cave and we were fighting kobolds and dragonborns but I will hold a natural 20 and one shot a dragonborn with my war pick and he said how do you want to do this because he already defeated the other one as it was to want to we both one shot but only I got a natural 20 and I had said “ I spin around pierce his head with my war pick and I decapitate him and just let the shower of blood rain down on me with some slight Disgust because it’s blood but I let it go on me because it’s cool and could later intimidated our opponents”