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

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

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

My sister has been playing a game and telling me about it. Every session her cleric gets traumatised in some way. Her friends are burned alive, her tribe is eaten, her favorite NPCs get slaughtered, her own party members that she gets close to end up torn apart - for one reason or another everyone she cares about ends up dead in front of her! It started out as just plot to motivate her, but most of it just came down to bad luck and worse rolls.

Early in the campaign, sis and her party adopted two dragon hatchlings. One of them, the female of the pair, bonds with sis. Basically, this dragon is like her daughter. Sadly, they have to send them away to another plane to grow up in safety, after which the dragons returned occasionally in adult human forms. One session, however, the party goes to an event that at the very end involves picking one of two boxes. One of the PCs picks a box and the other dissapears. Under the box is... The male of the two dragons they'd adopted. And the leader of the event wants the party to "sacrifice the dragon for the finale". This ends up with a big fight and the dragon dying.

Thankfully, with sis being a cleric she is able to revive him and they escape. She then asks him if his sister, the one who bonded with my sis after hatching, was in the other box. The dragon confirms it and my sis realises her character is going to lose yet another loved one.

So she prays really, really hard to her deity.

Nat 20.

Her god decends down in a shower of light with the female dragon in her arms. The god hugs my sis' character while she cries and thanks them, then kisses her softly on the head. The god claims she has suffered more than any other, comforts her over her losses, commends her on her bravery, blesses her, and leaves so that the party and their dragons may recover.



Two sessions later sis adopted an imp friend and an hour later it was one-shot in front of her via an arrow through the skull. So... back to the usual, I guess.



Edit: She rolled a successful divine intervention before turn one of the semi-final boss fight even started (it was against an elder brain dragon) and her god kamikaze'd herself to kill it in one hit. Sis had to reclass for the next (final) session.

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

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

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

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

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

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

6:49 you right about that, "lawful good" would accept rightful 1st time service fee wave for trickery

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

Two D20’s later, everyone is laughing their asses off and I have a flaming zweihander that can destroy souls.

I was a Human Monk struggling with alcoholism. Pathfinder. I took the Alcoholic flaw, meaning I'd have to make a Will (Wisdom) Save in the presence of alcohol to resist drinking it. I also took a few levels of Rogue for Sneak Attack because in Pathfinder there is a way to get Sneak Attack damage dice on unarmed strikes, during Flurry of Blows and it is just hysterically over powered.

Session Zero where we all meet up. Everyone at the table is meeting up in the tavern and talking. Everyone, except me.

I know, a drunk not in a bar? Whaaaat?

They leave and the DM says they find a disheveled man passed out on the outskirts of town wreaking of alcohol and piss next to a bonfire. One kicks my leg and I wake up.

DM: Okay go ahead and introduce your--

I SEARCH MY BACKPACK

you uuh, find your belongings?

Nooo, I want to roll to search. I'm a drunk and a thief. I want to know if I stole anything or lost anything.

Okay okay fine roll.

Nat 20. The very first roll of the game. Nat, fucking, twenty.

DM let's out an annoyed sigh, flips through the pages of the book and says I stole an Everburning Torch that (house rules) can be used as a +1 mace (1d4 bludgeoning + 1d4 fire) ((normal rules, EBT is magical, non-harmful fire))

And that, my dear friends, is how my alcoholic kleptomaniac Drunken Monk / Thief build got banned from ever searching his own belongings again ahahahaha

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

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

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

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

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

while playing a cheese-obsessed kobold rogue named Rat Cheeseman I rolled a nat 20 on a perception check that resulted in me finding a piece of pristine cheese on a notecard

In one of the first campaigns I took part in as a player, we had a party that consisted of myself (a fighter), a ranger, and a rogue. Our group was tasked with finding bandits hiding out in the mountains. We eventually managed to find their hideout and came across three guards that were spread out and watching the entrance of a cave. Not wanting to raise an alarm, the rogue and myself moved on ahead in stealth to try and take out two of the three guards while the ranger held back and prepared to fire at the third. The plan was to take out the guards all at once as there was just enough distance between them to potentially sound an alarm if we couldn't take them all out at the same time.

Anyway, the rogue gets near their target, the ranger is ready to fire at the second target, and I'm ready to dash in and slaughter the third. At that moment, the rogue critically fails their stealth roll. The ranger attacks and takes out the second target in one hit and needs to focus on saving the rogue. Meanwhile, my own target is alerted and running towards the cave. Not knowing any better, I do the only thing I can think of:

Me: I want to throw my greatsword at the bandit!

My two party members just give me this look that says "You can't be serious!" Once the DM stops laughing, he says:

DM: Sure, I'll allow it! He's only about 25 yards away, but I want you to roll at disadvantage since this isn't something your weapon is designed for. Roll two d20s and use the lower roll as your chance to hit.
Then the famous last words:
DM: Just don't go into this expecting to actually hit the ban.....
Me: Two 20s. That means I hit him, right?

At this point, my two other buddies playing the ranger and rogue are completely losing it and unable to breathe with all the laughing they are doing. Meanwhile, the DM is just completely dumbfounded that against all odds, the dice willed this completely ridiculous idea into being.

DM: That's...*sigh*...just roll your damage. 4d6 plus your +3 strength modifier.

In hindsight, I believe my friend that was acting as the DM was silently praying that I rolled low enough to wound the bandit, but not kill the bandit. I roll the four dice and come up with 23 once everything is added up. My friends are howling, the DM is just staring at my damage roll, and after a moment I realize the damage I did is far more than the arrow that killed the first bandit.

Me (unintentionally metagaming): I assume that a 23 kills the bandit? John killed his bandit with far less damage.
DM (still absolutely dumbfounded): Yep, this is really happening.
DM (now narrating): "The greatsword gracefully spins through the air before landing dead center into the back of the skull of the bandit and embeds itself up to the hilt of the weapon. The bandit stops dead in his tracks, stands for a moment, then slowly falls forward, but the body stops at about a 45 degree angle as your sword manages to perfectly balance itself onto its tip following a one in a million shot that will NEVER. HAPPEN. AGAIN!"

For the record, I did try to prove the DM wrong on that last bit in a future session only to have the dice extract their revenge as a natural 1 ensured my sword got embedded into a wall the next time I attempted my nonsense. The dice giveth, and the dice taketh.