As I said in earlier installments, I tend to GM, so many of my stories from the tabletop will involve the characters of other players by default.
The most audatious move I can remember dates back to high school. The mid to early 90s, RIFTS was the go to game for a group of GMs including myself, because we could go over the top, and that was all expected as a part of the setting. The "Atlantis" sourcebook had just come out, and it had introduced a Marketplace where "anything could be found", and the concept of intelligent Rune Weapons. Of course there were players who instantly wanted one, and since we played in a group where different players might take on GMing duties for a day, and where various players might have had two or three characters, each of whom had been played for a half-dozen sessions (or more), there was a risk to introducing one of these weapons into the game and totally unbalancing things. None of the characters had the money to pay for one of these things, so that was good.
We knew that if we handed out such a weapon as a prize for a quest, other players would start complaining about "playing favourites". If such a weapon were given to a weak character, they probably wouldn't be able to use it effectively (they'd be likely to miss attacks, before the impressive damage rate was triggered). So stronger characters would end up getting the weapon, and then prove totally unbalanced against the other players.
One player (one of my best friends at the time, and the person who would end up being the best man at my wedding), desperately wanted one of these weapons and he kept trying to convince other players to cut deals to get one. I discussed this with the other GMs, and offered a simple solution. A mysterious dealer with a wheel of fortune exists in the Altantean Market, no one knows who he is, his tent just seems to appear when its needed. Anyone may spin the wheel, either gaining a physical item of their choice, or losing their soul and "doing menial chores for satan" (this is the exact phrasing we used) for the rest of eternity. If the spin was negative, the character sheet would literally be torn up and burned on the spot, never to appear in the game again. If the roll was won, there was no guarantee that there wouldn't be strings attached, perhaps it was stolen and the rightful owners would want it back, perhaps it would be cursed in some way, either way it would push the story for the next few sessions.
The player decided to take the risk. Roll a d20 in plain view of everyone who regularly GM'd or participated in the game. Odds failure, evens success.
I can't remember what he specifically rolled, but he failed. It was a character with a year of play behind it, he was involved in so many stories and interconnected to so many other characters. Bang. Instant vacuum. Character sheet became a pile of ashes, scattered on the wind.
So it's not a tale of awesomely positive things that highlighted a character's abilities. It about a single moment when everything went sideways, though an event hinging on a single die roll that would change the course of destiny for another year or so until the game gradually wound its way down to nothing as everyone moved on from high school toward their adult lives.
The fact that his character is "doing menial chores for Satan" is something that's still mentioned in conversation more than 20 years after the event. It's moments like this that keep me attached to the hobby.