I was playing my first character and swashbuckler rouge and while exploring with the party came across a cave, we were getting worn down and about to have a tpk when we came to the boss fight but with a nat twenty and really hi damage roll I almost killed the boss in one shot. Everyone one at the table went crazy including the dm.

There is a certain descent in Sunless Citadel that is particularly bad to roll a nat one at, I found.

#DDBStyle

An excellent heart pounding moment was a recent weekly game I run in a homebrew setting. The party found themselves outside of a make-shift stronghold of an Orc encampment, that was fortified under a black volcanic range of mountains that expanded for miles in both directions. The group tracked this legion of six thousand orcs of the Thousand Fist Clan, from a previous besiegement of their home city of Capilarian, knowing that the Black Rock Mountains contained an ancient forge rumored to make legendary weapons of the highest quality and the Orcs where building a monstrous weapon based on scout reports. With that being said, the Dragonborn Wizard named Moros, using spells of invisibility, snuck into the encampment on a reconnaissance mission, dodging every patrol of Guard Orcs with wolves, sneaking past barracks, infirmaries, mess halls of countless number of Orcs, knowing that any failure of the dice would expose him. His scent was picked up by one of the Orc's patrols, but Moros was sneaky enough to evade them throughout the camp, however the encampment was closed off baring any chance of escape. The security of the camp was on high alert and searching for the intruder was doubled, knowing they were not alone in the camp. Not only did Moros end up stealing magic weapons from the Villainous Warchief Throg and random items off other Orcs too as they searched for him, but found the monstrosity that turned out to be a mechanized dragon and hijacked it from right beneath their noses taking off towards the sky.

Although the rolls where not all critical success or failures, its still intense knowing that your surrounded by six thousand Orcs is enough to make anyone lean on the edge of their seat with each roll. D&D can create some of the most memorable moments. #DDBStyle

An Icy breath from a young white dragon took me down. Rolled a Nat 20 on my death save. I stood up and fireball-ed an army of orc, who were followers of the dragon, into smithereens. The wizard lives to tell the tale! #DDBStyle

The biggest moment is my warlock going up against a strong fragment of his patrons mind. Had I not rolled as high or got another nat 20 my warlock would of been severely weakened instead the powerful bonuses he got by resisting jts influence. #DDBStyle

Played as a rogue once and I got a natural 1 when pickpocketing a "victim". The problem was the victim is a town guard and I am just trying to steal some sweet roll. The aftermath? My character was thrown into the cells. #DDBStyle

Playing LMoP. Evil wizard was about to get away. He ran across a rickety bridge. The party's Wizard fired a firebolt. Missed. Ranger pulled out her bow, everyone screaming. She fired at the ropes. Hit. Bridge collapsed, evil wizard fell into chasm, knocked unconscious. We all audibly sighed #DDBStyle

We've been playing this campaign for 6 months. After a journey to the Nine Hells and back my party finally realises that the good king they have been working for was actually Moloch all along, their actions all part of his game in trying to take over the Hells. The party consists of a wizard, a barbarian, a cleric, their horse, and a chicken. They arrive in the kings palace, confronting him whilst he is in the bathroom. They roll for initiative, and the wizard goes first. I (the dm) ask him what he wants to do. And he replies, "I throw the chicken". My face whitens. Having forgotten that they forged this chicken a magical beak-guard that allows it to kill one enemy if it rolls a natural 20 when thrown, I realise what is a about to happen. I ask him to roll. The dice jiggles in the palm of his hand, then flies through the air, bouncing once, twice, then slowly coming to settle. I peak out from behind my fingers. He rolled a 3. The chicken is launched through the air at the king, Moloch in disguise and hits him softly in the face. That was how my party annoyed Moloch and got themselves tpk'd. #DDBStyle 

Close to the end of our Curse of Strahd campaign, far from Castle Ravenloft but after Strahd had become aware of us, Strahd personally attacked us out in the wilderness after we'd made camp. Fighting Strahd as an exhausted paladin without my armor was incredibly intense. We were mostly out of resources and low on hit points. We finally did enough damage to make him turn to mist and flee, but it was a close fight on his terms.

#DDBStyle

Slave Pits of the Undercity. After several encounters ablated our spell slots and hit points, we went in search of a safe place to hole up and rest… right into an Orc barracks… we were holding our own until the orc chief entered the fray… half the party was down, including my cleric, and the other half were one bad hit from joining us. Nat20 death roll, popped up, and struck the boss with a hammer from behind, taking him down and turning the tide. #DDBStyle.

Had a Black Shadow Dragon land in front of a level 3 party. They thought they were toast. But all they needed to do was break an artifact that they had discovered to escape. The Tabaxi in our group dropped the idol, brought the sword down... natural 20. The idol exploded, and they ended up back on the material plane! #ddbstyle

5-6 session into our first campaign, my Goliath Shadow monk ran after our friend Who wanted to leave because a sucubus had impersonated her and tired to seduce another player.

He had a - 2 to his persuasion check, but with a nat 20 for 18 he managed to convince her that there was no one blaming her, that we needed her around.

#DBBStyle

Half way through a boss battle, my human archer rolls THREE consecutive nat 20 attacks, all using sharpshooter. The boss didn't last long!

#DDBStyle

I remember wanting to save a friend from a villain who traped him in a magic mirror. I was a Level 17 Arcana Cleric that time and I asked the DM to let me save my friend with Divine intervention. Up until that point, I was the unluckiest player on the table that night. I was blinded multiple times and I could not do anything as all my spells required sight. I even joked about how the Divine Intervention will outright fail as I rolled the d100 and got a 9. The whole table erupted into cheers as it was my first successful Divine Intervention, some players' first sighting of Divine Intervention and the DM's first Divine Intervention to deal with in his DMing career. #DDBStyle 

My party were chasing down a cup-bearer of the King, who was actually a Priestess of Lolth and was poisoning him. She was fleeing to regroup with two of her associates, who were also King's council members. My party made chase, slinging spells and arrows at her as she fled. Three intense rounds of as long-distance attacks and her trying to dodge, so many Nat 1s and even a Nat20. But she didn't go down and she made it to the gate, escaping for just long enough to recuperate before launching a devastating assault on the capital city. #DDBStyle

I was DMing and I was positive I was heading for a TPK. Two party members were already down and everyone had been rolling like poo, except for me, the DM. I seemed to only be able to roll high and had gotten multiple nat 20s. The Barbarian, with only a handful of hit points left, attacks and gets a nat 20, rolls for damage and gets almost max damage defeating the specter and saving the party. Still talk about it years later. The dice are half the fun of D&D

#DDBStyle

This was the very first session with me being a first time DM. So all the players had lvl 1 PCs.

They went exploring some goblin caves and got to a chamber with a bugbear leader. The party's paladin then proceeded to taunt the bugbear by shouting something along the lines of wanting to eat his bones. The bugbear responded by throwing a javelin right at the paladin. I rolled a nat 20 for the bugbear and the resulting crit took the paladin down to 1HP. He was a lot more careful of antagonising enemies after that.

#DDBStyle

My paladin oath of vengeance scored a Nat 20 on hit against the final dragon in Hoard of the Dragon Queen with his flametongue dragon slayer greatsword. Throw my highest lvl divine smite on top of hunters mark and did over 150 hp in damage. Nearly half the dragons HP, also that blow was the HYWDT! My heart was pounding! It felt great since it was that characters only HYWDT the whole module. #DDBStyle

A player in our game saved half the party by misty stepping on top of a dragon mid-flight and rolled a natural 20 to slam his greatsword into it's head from above. #DDBStyle

Fellow PC killed the recently turned (into vampire) son of a priest in a town and tried to intimidate the priest into becoming his slave while he was grieving. #DDBStyle