Back in high school I managed to play, as opposed to DMing, a lot more than I do nowadays. Quite a bit of this play was in the one Killer DM game I've ever really encountered. This is the DM that started one fighter of mine pre-raped and who colluded with the players to pull all sorts of shenanigans on each other. We put up with a lot from that guy (though sometimes we pushed back, too) but he also was an adult running games for schookids, so he probably put up with a lot from us as well.
Anyway, although it wasn't a conscious design process I'm pretty sure that the concept for Chester of the Pointy Hat came from two sources. First, H.P. Lovecraft's works and Call of Cthulhu were new and exciting to us back then. I was (and still am) in love with the concept that reading musty old spellbooks drives you mad. Second, I'm pretty sure that around the time Chester was rolled up and played that I saw on something like 20/20 or 60 Minutes a report on the effects of the defunding of the mental health care system under the Reagan administration. [Please no politics in the comments.] As is typical of this sort of reporting, the tone was "Holy crap! Homeless schizophrenics wander our streets! They are going to break into your house and molest your blender!"
So thus was born Chester's personality. He was driven mad by his arcane researches, but not in the cool, Gothic, brooding, cackling sense you'd expect, but rather as a smelly, pathetic, muttering bum. I refused to sleep in inns, opting to hunker down in rain barrels. (The DM obligingly rolled to see if I caught pneumonia.) I ended up getting kicked out of and barred from most taverns the party frequented, for being noticeably more unhinged than a standard PC. Johnny Law got involved when in revenge I lit one tavern on fire. Not with burning hands or fireball, mind you. I just stone cold walked up to the exterior wall of the joint and assembled some kindling and got out my tinderbox, right in front of everyone on a main street in broad daylight All in all, I thought it was an interesting character to play.
Of course he died. Like I said, it was a campaign with a Killer DM. And playing my MU as mentally ill wasn't exactly going to do the poor sap any favors. Still, this death is one of those incidents that, in retrospect, makes me question whether Jim was a Killer DM at all. Maybe he was just playing fair and we were all idiots. He was our first DM outside of my original game group. The lot of us were self-trained; we started with my Basic Set and had no clue what we were doing. Maybe it was just a School of Hard Knocks campaign.
Anyway, we were going after a dragon. This was super exciting for us. There had been a few dragons in our previous games, but this was our first time that A) we knew that a dragon was in the dungeon and B) we had made a conscious decision to go after that lizard and take his loot. We started out doing everything right. I think we had just acquired a Dragon back issue with an article on successful tournament play and we were making a bit of an effort to use the guidelines therein to be more professional in our dungeon pillaging. So as stealthily as possible we scouted out the whole dungeon level in advance and ended up with a graph paper masterpiece with a big blank spot behind a pair of big double doors. That had to be the dragon's lair. Even better, we located it with the minimal possible resources expended and no casualties.
This is when our new professionalism all went to crap. We started arguing, loudly, in the middle of the freakin' dungeon, about the best plan to kill that dragon. I'm pretty sure that after a few minutes of name-calling the DM started casually flipping through his copy of the Monster Manual, but we were too dumb to realize that meant he probably was looking up a wandering monster attracted by all our shouting.
In fact, he was double checking the range of a dragon's senses, which I'm pretty sure in the original MM is duly noted in inches. So when my crazy hobo MU5 declared angrily "FINE! I don't care what you assholes do! I'm going to open those damn doors, throw my fireball and you can clean up whatever is left!!!" what I didn't know was that the dragon heard the whole thing. Out of 'kindness' the DM didn't make me roll to open the doors. I flung them open and promptly melted under a torrent of acid. Black dragon.
As I recall, the rest of the party ran like hell. And like so many sessions before and after that one, I started a new character.
At this remote point I can't recall much else of Chester's career save for a random encounter in a forest. The DM rolled up gnolls on his wandering monster matrix and looked up the number appearing in the MM, which is something like 30-300. The dude literally rolls every d10 on the table and declares "You round a corner and approximately 200 gnolls attack. Roll for initiative." We took the bastards in the longest single fight of that campaign. We used every attack spell, sleeping and fireballing and Melf's acid arrowing as many as possible, but they still kept on coming. The archers in the party shot until they were all out of arrows. They still kept on coming. My puny dagger-wielding magic-user spent more rounds in melee combat with those bastards than some MUs will melee over their entire career. It was incredibly stupid ("We come round a corner, in a forest?" "I set 35 of them on fire with magic and the rest just keep coming?") but also one of the damnedest damn fights I've ever played out.
The PC casualties in that campaign were ridiculously high. Just getting from the beginning to the end of the session with the same PC was an exhilarating victory. That's why I'm all for save-or-die, level drain, zero level funnels and balanced-dungeons-my-ass. Not because I'm enjoy forcing players to suffer the same way I did, but because I want them to experience the high of just escaping the session with your life.