What was the edgiest player and/or dm character you guys had to deal with?
A few years ago I was preparing to run a short campaign with a small group of friends in 5e.
It was going to be a two or three session dungeon crawl through some completely trap infested ancient ruins.
One of them went with the idea of being a small orphan child who investigated ancient ruins in order to scavenge items and make a living.
After hearing this, another friend came to me and told me his genius idea for a character. He thought it'd be great if he was the guy that made this orphan an orphan, which, on it's own is not bad.
The part where it crossed a line was when he went into autistic detail about how he mutilated the parents and had been stalking this child, waiting for the moment to finish the job.
His goal was to try and kill the entire party, which I made very clear would be a thing he could do by abusing any of the traps in one of the first rooms they'd be likely to enter, but he didn't care.
He went on to explain that his character's backstory was that he was nihilistic and his goal was to inflict the most amount of suffering he possibly could on the world and he'd gladly kill himself if it also meant he could make someone else suffer.
So he wanted to run a nihilistic, child murdering, edgelord, who wanted to kill everyone else and had no self preservation instincts in an instant kill trap laten dungeon.
The way I dealt with this was by telling him "no" which he did not appreciate and bitched about it for quite a while.
He eventually came back with a different character who was thankfully not another edgelord but he wanted to play an Eldritch Knight but he also wanted a bunch of magic items from the artificer class which still wasn't officially out at the time.
In this character's backstory he just threw in some line about "oh yeah they have an artificer friend who gave them all these magic items".
I once again told him no and explained that if I let him do this I'd need to let everyone have off screen artificer friends who just make magic items especially for them. I also explained that if one of the remaining two players who was still working on their characters wanted to play artificer, someone else just awarding themselves a bunch of magic items which are meant to be main features of the artificer class would kind of ruin what was supposed to make the class special for those other players.
He actually threw a bitch fit and tried personally insulting me over being told that he wasn't allowed to just have 5 more magic items than everyone else.
He is now an ex-friend but that's unrelated to this, though I'm sure you could imagine why that may be.