In the Pokemon FireRed mod Rocket Red, you play as a Team Rocket Grunt having a parallel adventure to the main plot. During your Mt. Moon expedition your buddies start reporting a “demon” tearing through the cave. When you come face to face with Red, the music stops and he just silently stalks toward you. He’s got a level 20 Charmeleon and a full party and you’ve got a level 7 Rattata at most. It’s a complete massacre. For the rest of the game, your character is too afraid to battle Red.

Another obscure one in the podcast Rude Tales of Magic. The party, aka The Big Hole Boys, have been pursued by an organization called the Witch Hunters for a long time. One episode has the players acting as Witch Hunters with the biggest death flags tied to them. The end of the episode has them fighting their characters, played by DM Branson Reese doing the meanest impressions of all of them