Could've Sworn I've Heard This Tale Before...
Context: We were at a tea house/inn in response to an ad for an entertainer, since my Drow elf was the only one who had an entertainers background, I had to entertain the patrons there to get us a place to stay for the night
DM: They look expectantly to you for a story.
Drow: I’ll tell a classic tale about a hero rescuing the princess.
*proceeds to roll a 4 for performance*
DM: The lady who owns the tea house suggests that you tell another story. Fast.
Drow: Uhhh okay I tell a tale of a halfling who lived in a hole who one day gets recruited by a mage and a bunch of dwarves to rescue the dwarves’ fortune that is in the mountains that were once their home, guarded by a dragon.
DM: ….roll for it
Drow: *proceeds to roll a natural 20*
DM: The halflings in the tea house give you a standing ovation. There are tears being shed. Everyone has gathered around you to listen. Someone in the background says “wait. I’ve heard this story before…”
Needless to say, it was the best timed natural 20 of the night.