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The "devil at the door" thing reminded me of this party member of mine. Tiefling Fiend or Hexblade Warlock, the player was gonna move soon. Basically, the group was in severe danger, so he phoned in on this pact, and this ancient Moonblade his family owns appears in his hand, and these tiny metal tendrils pierce his arms, and start draining his blood to power the sword. He can't take these out without depositing the blade, and he takes a small amount of damage per turn. He basically gets to choose what powers the runes give, so he's got a Vorpal Sword and a Shadow that works as his minion. We all work together and tear through the enemies, and at the end, the Duchess of Avernus pops out of a mirror, and my character makes a goofy joke complimenting the Warlock guy. He promptly gets his eyes set on fire, but one of them was made of stone anyway, so it only hurts an incredible amount. So, this Warlock says goodbye to everyone, passes around a couple magic items, and walks through the mirror with his patron. The wires fall out as his body burns away, and in its place, a hand lifts the blade. A Pit Fiend steps out of the smoke, and smiles. Greatest character send-off I've ever seen, and I've had a guy sacrifice himself, murder the head of an enemy force, and fight the others off until he died of exhaustion.I haven't had anything I played in last long enough to sort of be more than "neat" but I would submit Gur-Shaak from the same campaign as Bambu's Imastrius. She was a Jungle Orc (not half-orc, full orc) Barbarian with 20 strength and 7 intelligence, and I like to think I struck a good enough balance at playing her as somewhat of an idiot without being too annoying. Plus she was just fun to play because she would trip someone, kill them in one hit, get a second attack and kill someone else in one hit on basically every turn, I think she probably had as much of a body count as the rest of the party combined (though our Druid definitely ended up carrying way more on the harder fights).
I don't think I'm 100% happy with her as a whole but my first character, Lilli a Fairy Rogue, had a pretty fun (read: absolutely ******* abysmal but in a fun way) ending, her cleric friend died while they were trying to stop some bad guy, so she literally just made a deal with a devil (thanks to a very conveniently nearby item) to revive her, and what the devil was probably expecting was to bring her misfortune through the cursed hoard she also got, but then she left in shame and the cleric gave away all of that cursed money to poor people which means literally the entire country got hit with the curse. The bad guy that they failed to stop ended up causing tens of thousands of deaths before being stopped, the cursed money caused hundreds of thousands with no obvious end to the misery in sight. And then a devil came knocking at her door.