Early in our campaign, our DM revealed his big bad - a fully grown blue dragon. We were supposed to hide until it left, but our party decided to take some potshots at it. Then our rogue comes up with a "brilliant" plan to lasso the dragon. I was sure it would be a tpk, but two nat 20s and some unbelievable dex saving throws later we actually managed it. The look on our DM's face when he had to crash the dragon into a wall was priceless! I secretly think he's been trying to kill us ever since. 😋 #DDBStyle

A session in Tomb of Annihilation comes to mind for me, I was a Half-Orc Fighter Warlock in a gladiator arena, fighting three Velociraptors after taking one down, the other two almost had me downed, I was 2 HP away from death, praying to the dice gods that they would miss, and then I hear the dreaded words from my DM, the Velociraptor crit you, my heart sunk I was downed, against two Velociraptors by myself when then he started having the entire party roll Charisma checks since they were trying to rouse the crowd into support for my Half-Orc, all around the tables were Nat 20's as everyone's heart started racing as then I had to make the final roll, I succeeded on the DC he put and got back up on 1 HP, round goes back to me, and I managed to finish them off on my next turn. #DDBStyle

In the module the tome of annihilations we were infiltrating a pirate base and successfully kidnaped all the pirate captains without anyone noticing :) #DDBStyle.

So my party got in a fight with a Marilith. The odds for them were not good. This things attack rolls average at 19.5 with 7 attacks a turn, averaging damage was 13 per hit and it has magic resistance, on top of that its resistant to the elemental damage the party tends to deal out. This thing could TPK them and I was pretty it was going to take out at least 2-3 of them and force the rest to retreat.

The ranger is dead, the cleric has some heavy wounds, the warlock and one of the bards had extremely little hp, so its multi attack would kill them. Its the nearly dead bards turn, she uses her turn to cast hypnotic pattern. Thats a wisdom with a DC 15. The Marilith has advantage with a +8. Each roll had a 65% to beat the DC. Now hypnotic pattern would change the fight completely because it incapacitates the target for 1 minute with no saves at the end of the targets turn.

I make the saves and I roll a 3  and a 6. It failed and the ranger was revivified and they got away. And I didn't have to kill all my players.

#DDBStyle

Also have some of the worse "waste's" of a nat20: In an office building, looking to meet a new party member. What do you know, they were sitting at their desk in their office. However, what he didn't see was the newly joining monk who was hanging up in the ceiling above him not sure how to introduce himself.

It was a home-brew game. Many adventures finally led the party to the lair of a pair of green dragons. The heart-racing moment took place at the end of the long, white-knuckle battle. Here below is an excerpt from our game notes:

For the first time in his long life, the ancient Green Dragon, Ixtar The Great, looks unsure of himself. He rises high into the air and glares down at the party. He looks over at his dead mate and lets out a low howl. His eyes fill with hate and  lock onto the fallen Warforge Fighter, Aggressive. From 100' up he swoops down at the unconscious automoton, with his talons outstretched in front of him. The rest of the party gasps as they come to realize what is about to happen. It takes mere seconds, but time seems to stand still, in slow motion the injured dragon grabs Aggressive like a limp piece of meat. He quickly climbs back up to the sky and turns, flying away towards the hill.

The rest of the party looks on in dismay, they realize that the fate of their heroic, unconscious friend is more dire than ever before.

As the dragon approaches the topless hill and the muddy hole of its lair,  he slightly rises, looking for a good place to drop Aggressive (we think?) Aggressive needs to take another death saving throw.  If he has any hope he needs to wake....

HE PICKS UP HIS 20-sided DIE AND ROLLS AGAINST FATE. AMAZINGLY, HE ROLLS A NATURAL 20!!!!! Aggressive wakes!!!! If ever there was a time for a natural 20!!!!!!!!!

The warforge stares around and sees his predicament. 100's of feet above the volcano floor in the clutches of a dragon bloodied nearly to death. He himself barely clinging to life, his mind begins to process his options. What will he do...?

Aggressive dangles from the dragons claws. He has made  a miraculous recovery and now ponders what to do. As he does, the badly wounded dragon heads towards his cave, Ixtar surveys the landscape, looking for a suitably hard and pointy place to drop the warforge. 

The rest of the party looks on in helpless desperation, Aggressive attempts to wake silently so as not to arouse Ixtar's attention, but his bluff fails to make it!

Ixtar sees that his prize has awoken! He immediately drops the warforge! Aggressive desperately scrambles at the dragons claws, he clings to one claw as the dragon flicks at him with the other. Ixtar turns wildy in the air as the warforge grips tight, it takes a barrel role and curses “why won't you just die!” with that he snaps at the warforge with his maw and Aggressive is forced to let go with one arm to avoid the bite. Aggressive hangs on one of the dragons claws and looks up, he yells “wait we should discuss this” for the briefest of seconds the dragon pauses, his eyes look through the warforge, and for a moment there might be something. The dragon smiles wickedly and flicks his foot in a whipping motion.

Time seems to slow down, the warforge feels his grip slip and he swings out his hands in desperation but he only finds air. This is when time picks back up, as gravity takes over........

In mere seconds the Warforges bulk picks up pace, he hits terminal velocity and begins his rapid decent. As befitting the warriors pride he looks to his fate and leads with his head. The ground approaches quickly and images of his life flash before his eyes. Battle with his comrades and bounty gained, and lastly the little girl. Aggressive “I will be with you soon little one”........darkness

#DDBStyle

Not long ago, I was playing Curse of Strahd, and then Count Strahd himself appeared on the battlefield with several vampire spawn, after some unsuccessful attempts to kill the spawn, Strahd tried to drag one of my party members, who was randomly selected, and by the way, was my girlfriend in real life...Quickly, my Bard (Neutral) went on top of Strahd to rescue his party mate (girlfriend)...I threw a die as the DM asked, the dice rotated a few times and then...I got enough to catch her and run. One thing I know, I saved two things that day haha. #DDBStyle

My party was in the middle of a high tension conversation that was beginning to raise suspicions. Things started to look bleak as our GIANT ROGUE misspoke. This alarmed the woman we were speaking with so our brilliant giant decided to hide in mid conversation. He, of course, rolled a nat 20. He seemingly vanished into thin air before the woman's eyes. Now this REALLY raised suspicions so I did my best to deceive the woman. I then rolled my own nat 20, my DM asked me what I said to deceive her. I told her "Hey lady you're crazy, there never was a giant" She then had a mental breakdown, and in turn, we skipped her as a minor boss fight. #DDBStyle

#DDBStyle clearing a dungeon and someone escapes. A few sessions later we are ambushed on the road, I'm a gnome wizard with nowhere to hide. I'm lifted into the air and dropped.

Reaction feather fall. On the way down I get hit and knocked unconscious. Death save nat1 then a fail

#DDBStyle

I was running a homebrew adventure from level 1 to 5 with a group of friends. They had just escaped a prison (the initial setting of the campaign) and were taking a long rest by a river. At the end of the long rest, 2 crocodiles attacked the party! This was supposed to be an easy-medium encounter without big problems. However, one PC went down after one crocodile had a natural 20. After falling 3 times in a row, his PC (with a complex and well-done backstory) just died before reaching level 2... Sad

Same campaign, (a bit later) another PC tried to deceive a merchant by selling the crocodile skin (yup, the same 2 that killed the PC) as "dragon skin". Rolling a Nat20 in deception, the merchant was fully deceived. He offered everything he got to obtain the "mighty dragon skin". The merchant finally went bankrupt...

We were fighting Acerak in the final battle of Tomb of Annihilation after spending more than a year getting there. Acerak was looking tough but our paladin/warlock hits and smites Acerak, he then follows it up with a crit and uses both smite and eldritch smite. Acerak still wasn't easy, especially after the trouble we'd had with the soul monger and the Atropal but it was memorable. #DDBStyle

in the death house first time playing used mage hand on the door to rankor the shambling mound in the basement it failed it's save to lift the door so we piled a bunch of wood and torches and bon fired it the dice were with us that day https://www.facebook.com/hashtag/ddbstyle?__eep__=6&__cft__[0]=AZX0NkFewU8sJVCEozjS-ANV5f-Y4ZCSqoCI5t2zXuqDiwiOwZKp-6qReeVyhV88g_EHEOJpm2TgpKl0Mr5BCJS9hHFJKLi-qQ5XJ65QamFt9VKcBeDGsPA75yW9xInkf4K7NhH6YU7_vA7-SHijxoTh&__tn__=R]-R">#DDBStyle

The first time I used digital dice playing in our latest homegroup.  I rolled exceptionally poorly and went back to rolling physical dice.  
#DDBStyle

My party and I became aware of a beholder beneath a city, quietly exerting influence and subverting the citizens. After a long dungeon traveling down into the Underdark beneath the city, my party was faced with the beholder. Fast-forwarding, three of my party members were unconscious,  one dead, and another becoming petrified. My warlock Abrax, now down to 3 hp, cast Banishment. The beholder failed its save by 1. Abrax was then forced to hold the banishment for one minute until it became permanent, all while his companions and fiends bled out around him. The high of the beholder failing its save was quickly followed by the sadness of being unable to save his friends. We saved the day, but at great cost. #DDBStyle

A long time ago when I didn't know how to deal with troublesome players, I had one who was continuously player bashing and character slashing. I decided to have his character meet its end in a terrible accident so I set up the scene with a half dozen Ankhegs in a field of high grass. The party of five adventurers made camp just as I predicted and I lured the doomed character out into grass with Natures calls. When his trousers were down the Ankhegs attacked! He fought valiantly, naked from the waist down. I knew the 3rd level thief had no chance! The rest of the party rushed to his aid and also fought with some great effort but is was a loosing battle. THEN, Oh wait there is that Natural 20 that happens to come along when you least expect it. Even worse NOT one, NOT two, but THREE of the players rolled them one right after another. The party (who were also tired of him) ended up saving the Thief. Fate caught up to him when he later slipped from a ledge (classic) and fell 35 feet to his death. I know what you are thinking but NOPE I didn't manipulate that one at all. *Darn*  #DDBStyle

Many years ago, I was playing as a druid with skill in brewing. While we were sitting around the campfire, we got ambushed by a werewolf. We were freaking out, and the nearest item i had at hand was a jug full of spirits, so I thought I would try to throw the liquid THROUGH the fire at the werewolf. The other players thought it was ridiculous, but then when I rolled a natural 20 and the werewolf went up in flames, they changed their tune real quick. #DDBStyle

As my cleric faced an undead T-Rex in Tombs of Annihilation, rolling....holding breath as the dice were unleased.

#DDBStyle

This happened somewhat recently in a game I was DMing. The party had been given the task of hunting down a man known as Walden Jos and his fellow hunters several sessions ago, and after several real life months they arrived in the extremely dangerous jungle known as the Sanguine Forest where the man was supposed to be. They journeyed through until they arrived at a small temple, where Walden revealed himself. After a bit of banter, and a couple of failed deception checks, battle ensued. Revealing his true form to be that of a unique variety of fiend, he used the Reverse Gravity spell and some clever tactics by his companions, very nearly beating the party, and in fact even killed the ranger’s animal companion. However, the ranger loosed one final arrow straight into Walden’s chest, enraged by his beloved ape companion’s death. Striking with the power of a natural 20, the arrow pierced the devil’s heart and sent him back to the hells. Mourning the loss of one of their allies, the party then began recovering from a fight that took up most of a 5 hour long session  

#DDBStyle

Me and my party were surrounded by a large group of enemies who were run by an adult white dragon, he said he’d call them off if we agreed to a duel. So to save my party I accepted and squared up with him at only level 8. The bard of my party casted a spell, whose name escapes me, that started a long chain of chip damage. The dragon had used a breath attack and everyone had failed before I remembered our bards spell hadn’t ended, mind you I was almost unconscious by now. I reminded our DM about the damage the dragon needed to take and our bard rolled his die, dealing exactly the 4 damage we needed to defeat the dragon. Everyone at the table was almost in tears of joy. #DDBstyle

my #DDBStyle has to in the ultimate battle in Castle Ravenloft against Strahd.  I was GM'ing the game and I really wanted to push the team to their limits after such an awesome campaign.  We were fighting in the catacombs and Strahd shifted through a wall for a hit-and-run attack and punished the group's paladin when the group got split up.  He needed a huge roll to avoid having the tables turned by a smite.  The PC's won the day ultimately but there were a few moments in an epic fight where they needed a timely save to win.