What is the stupidest thing you’ve rolled a nat 20 on that turned out to be brilliantly executed? /u/BioWench DnD: Roll for Initiative!

Tell me about a time when the stakes were low, and you succeeded spectacularly, or when the stakes were high, and you made a decision that was often regarded as bad, but it turned out alright because of a natural 20 roll. I’m not talking about taking risks and doing well; I’m referring to the lamest, most boring, or downright stupid ideas you had that turned out well because of a natural 20 and a Game Master with an imaginative flair! How did people react? Did this moment change anyone’s course in the game? Were any ongoing jokes developed from it? Spill the tea, sis!

Tell me about a time when the stakes were low, and you succeeded spectacularly, or when the stakes were high, and you made a decision that was often regarded as bad, but it turned out alright because of a natural 20 roll. I’m not talking about taking risks and doing well; I’m referring to the lamest, most boring, or downright stupid ideas you had that turned out well because of a natural 20 and a Game Master with an imaginative flair! How did people react? Did this moment change anyone’s course in the game? Were any ongoing jokes developed from it? Spill the tea, sis!