One of my first games, I was about to lockpick a super hyped up treasure chest but before I said I was going to try it, one of my other party hit it with an axe with a natural 20. Then I rolled to see if I could catch the expensive looking fancy potion, but rolled a 1 so it shattered on the ground right before I could get to it.

And so started my legacy of comically bad/low rolls.

All the many times that I as DM gave the PCs an encounter, and they found a way around it without fighting. Those are always fun to watch and see what players come up with!

This is from my first campaign and I remember it clear as day because it was the first time a nat 20 saved my ass big time.

The party wizard and I were exploring an abandoned building in town and we were attacked by a large rat which I tried not to kill but I bit the wizard and nearly killed him so he used thunder wave and rolled max damage. Unfortunately it was also enough structure damage for the building to collapse and it was loud enough that the entire town came outside to see wtf just happened.

Now our wizard didn’t protect me from this spell so I’m basically deaf and nearly dead. Upon seeing this gathering of villagers I try to cover our ass and shouted “THERE WAS A MIMIC!!”. I rolled a nat 20 for deception and after that we were treated very well by the villagers