We were a level 7 party of 5 players. A tabaxi artificer, a wood elf ranger, a firbulg monk, an eladrin druid, and a human rogue/bard, going up against Juibilix, demon lord of Slime who was summoned into material plane by one of the player's former character.

We spent 5 sessions preparing for the big battle against Juibillix. When it came down to it, we all agreed us players would do public rolls (aka roll in the middle of the table) in this potentially world ending session. Not a single one of us players rolled below 14 that session!! We almost lost the druid after they went unconscious inside the demon lord! DM were not kind to us and used his "Player killer dice" and rolled pretty high himself. We managed to defeat the demon lord and celebrated the session after with a cake with the following text: We defeated a demon lord and all we got was cake"

My first campaign was playing 2E. I was playing an Elven ranger, and I acquired an arrow of dragon slaying in our first session - our DM allowed us to get one magic item. Being my first campaign playing, the word 'Dragon' stuck out in my head, so that's what I went with. A couple months went by, and one day our Big Bad finally showed their face, and it was a dragon. As the dragon is boasting, I raise my hand and asked my DM if I could take a pot shot at the dragon using my Arrow. He laughed, and said sure, but it'll only kill if I roll a 20.

I did.

The session ended about 10 minutes later, and we went on hiatus for a month while Gordon refigured the campaign. He got the last laugh though. I never rolled higher than a 13 the rest of the campaign, and eventually got into a situation with something like a deck of many things that he had dreamt up 100 possibilities of on, and we each had to roll the dice to advance through a particular part of adungeon.  That's where my characters gender was changed from male to female after rolling a 02 on percentiles. It was a fun campaign - I got to really flex some roleplaying muscles having to change the base nature of my character after that dice roll. I miss that group, and Gordon. 

#DDBStyle.

We were a bunch of low level characters facing an angry vampire who put down everyone except the ranger. In order for us to win, ranger needed to win init and roll a 20 with the vorpal sword. Player wins init, rolls a nat 20 every1 goes wooohooo!!! #DDBStyle

My fellow Dwarf crew mate and I decided to koolaid man through a wall to get the drop on whoever was on the other side. At first we failed but we persevered and got through that wall on the 3rd or forth try. Shockingly enough no one was surprised when we finally burst through.#DDBStyle

A L3/4 Rogue/Warlock Nat 20'd a stone giant with a giant-slayer bow with sneak attack damage - rolled almost full damage on all dice, dropped the giant.

#DDBStyle

I would be lying if I said any roll made my heart race.  There was a game in 1980s where one of my players fliped the table in frustration that made my heart race.  He had a string of bad luck and chose to be confortational alone in a dangerous area.  His character died.  After explaining that this game wasn't the end of the story, and helping him build a replacement character while the rest of the group could save or to resurrect him.  He calmed down and never flipped a table again.  I learned back then that even your friends who say they understand the rules need guidance on how the game is different than reality and to have patience with them.  I also changed the game to be a little easier over time, realizing that for story reasons a player might spilt to handle more goals in the same area of varying difficulty.  

D&D is fun but, it's not the only game system out there.  I've enjoyed storytelling in many game systems.  I still think it's a little disapointing I have to search for other services to use different systems, but there is no game pass or steam of TTRPG is there?  I'm entering because I strategically bought books on here and could use the books I didn't buy to include more options for the players in my game.  If I don't win, it will not really effect much more than that.  Thanks for continuing to be a good source for Wizards of the coast.  #DDBStyle

This was the one that set the hook:

My family and I started playing D&D together in January of 2018 - my daughter, merely 5 at the time, was extremely excited to start playing Lost Mines of Phandelver.  She took on the role of the party Wizard and we ALL still remember the point at which they encountered the Redbrands in Phandalin.  After the leader of the Redbrand thugs confronted the party out in front of the Sleeping Giant taproom, my daughter responded to the Redbrand's taunts about the "little puppies" with a Burning Hands spell.  Since I was still relatively inexperienced with 5e at that point, I mistakenly had her roll a ranged spell attack.  The Natural 20 resulted in a cheer from everyone at the table as she reduced the lead ruffian to a smoking cinder pile in the middle of the street.

It did have an unfortunate side-effect, albeit a brief one: she began trying to drop the D20 to result in a Natural 20 during the following session.  We talked about it afterwards and she's been a critical party member ever since.  No one messes with Princess Mira!

#DDBStyle

I was in my DM’s campaign ‘Fall of Haven’ and the party was ambushed by a giant toad and a group of bullywugs. Being as my character is an elf rogue, I thought it would be a good idea to go for the bog toad  I managed to gain advantage and rolled a critical. The damage was beautiful. What I had miscalculated was the damage it could do with me. Unfortunately I didn’t dodge and the frog rolled a critical against me. Couldn’t believe it. I was there lifeless and the in the frogs mouth. I failed my next two savings rolls and thank fully one of the party finished the frog off and a was dropped prone. 
It was one of the best encounters I’ve ever been apart of. 

#DDBStyle

My favorite moment was when my party was on it's last legs against a wizzard, and my ranger rolled a nat 20 on a sharpshooter shot. I did enough damage with that to kill the wizzard, and the DM flavored it as a "shot through the heart" causing us to sing it every time that character would shoot things. 

I was running a campaign and the group came across a Red Dragon the rogue had a Scimitar of Tusmit from Greyhawk. The party was down and out so the Rogue threw the Scimitar which is like a boomerang of Sharpness and Rolled a 20 then had 1 in 8 chance of the head being cut off and rolled a 1! Killed the Dragon and made off with the hoard! #DDBStyle

I was running Lost Mine for some friends and the party's Celestial warlock nailed a crit on Klarg with his Guiding Bolt, and with the damage he'd already taken from a wolf bite (courtesy of the cleric's ace animal handling check), Klarg got turned into a pair of smoking legs. BEFORE HIS FIRST INITIATIVE EVEN CAME AROUND. #DDBStyle

A vampire jumping the party in Undermountain, smashing the Paladin, and putting the whole party on edge.  Paladin returns with 3 critical on the trot, smiting each time.... Vampire on the run and the Paladin showered in glory, albeit from himself.  #DDBStyle

Once, fighting a magical cult boss in a cemetery, we were being blinded by a magic fog, not being able to see anything. Decided to sprint to its last known position, jump and do a flying kick to his chest. Rolled a Nat 1, tripped over, broke my leg and tackled my friend. #DDBSTYLE

Really showing the power of a tempest cleric in the Tomb of Annihilation.  #ddb-style

Was rolling for sneaking around a huge gathering where my character's group was being hunted and I was rolling to hide and I had been playing this character for so long I was scared they would die #DDBStyle

Rolled just enough damage on a bead of fireball to save the party from a TPK as we tried to escape on a flying broom from a bunch of monsters! #DDBStyle

Oh man! While playing Curse of Strahd, my Rock Gnome Artillerist Artificer directed her tiny dragon homunculus servant (named Tad Cooper) to try to stealthily pick a lock on a suspended cage to release some trapped birds inside. Rolled a Nat 1 trying to pick the lock. This alerted everyone around AND the birds inside who promptly grabbed Tad Cooper and pulled him into the cage with them. The birds immediately started pecking at him. Queue facepalm and uncontrollable laughter #DDBStyle

I was DM'ing for my regular weekly group and they were entering an ancient tomb where a necromancer had previously left several spirits and other undead nasties as guards. As undeadies started the combat with the party, I had a specter swoop in an attack the party's necromancer-wizard. I rolled a nat 20 on the first attack. Nothing bad yet, I tend to roll a lot of crits against my players and a level 5 character should be able to handle an attack from a challenge rating 1 creature, even if it's a crit, right? I rolled the damage and it came up really high. Now I was starting to sweat and asked the player to roll a constitution saving throw against the specter's life drain effect, and she failed. This meant that the damage done would reduce her maximum hitpoints and as the monster manual reminded me; "The target dies if this effect reduces its hit point maximum to 0". I nervously asked what her hitpoints were, and was shocked to learn that the damage was higher than the frail wizard could handle. The irony of a necromancer being killed by a random specter also hit me.

Now I'm not against character deaths if the players get in over their heads, but an undamaged player dying to a one-shot kill in the first round of combat due to some fluke dice rolls combined with a specific mechanic? It just felt a little unfair. I gave it some thought and ended up going a different route. Instead, I had the specter posess the body of the character (I know it's technically not an ability on the statblock, but if ghosts can do it, why can't specters?). Since the character was a necromancer herself and is an expert on spirits and other undead, she was able to resist it from taking full control of her body, but it still remains somewhere inside. The ancient spirit's memories combine and clash with her own, and sometimes thoughts or feelings surface that are indistinguishable from her own. So a few rolls that at one moment looked like something of a disaster and a very unfortunate session for one of my players, was turned into an important and interesting story hook that I might not have come up with had the dice not put me on the spot.

#DDBStyle

In my first campaign ever, my Dragonborn Rogue was the last party member standing (of 3) in a fight against a caster with Greater Invisibility and Fireball. I had passed both saves for earlier fireballs but both my other party members were downed from the most recent one, which the monster let loose after it blocked all three of our readied spells. I opted to attack the monster with my rapier and landed the hit, but it lived. Then, I used my bonus action to attack with my dagger and rolled a Nat 20 to kill it, effectively saving us from a TPK!

#ddbstyle