I was reading through some of the magic items in my DMG as I was contemplating Yet Another AD&D Campaign (tm). This is a biannual event that brings me much delight initially but usually fails to materialize on some level . Anyway, I noticed that no game I'd ever been a part of included most of these items. Nearly every game has a Bag of Holding or Ring of Invisibility at some point, but no Robes of the Arch Magi nor Drums of Panic. And that's a real shame because some of this stuff is pretty interesting and would generate a lot of amusement value. I do remember running a game wherein the ranger found a Ring of Delusion and thought he could fly. That added all sorts of family entertainment. I suppose most of this stuff would destroy a low-level game, so that's probably why I've never seen it or used it.
This led me along the path of wondering about high level characters and if people ever really did/do play campaigns long enough to cast 9th level spells or become the Grand Druid. I've certainly been a part of games that had these features, but usually they started at a high level initially. This is only related to AD&D specifically for some reason. One summer when I was in high school we played D&D all the way through 36th level before the characters became immortal, but I've never had an AD&D character who experienced the same thing. My 15th level assassin started at 10th level, which kinda sucks because playing out all the lower level murdering would have made for a better back story.
Anyway, browsing through The Rogues Gallery, I noticed the stats for some of the original D&D characters like Bigby and Erac's Cousin. Obviously these characters progressed organically, meaning they gained power and ability in-game. And you can tell looking at their stats and equipment. Further, most of them are around 12-15th level max, a far cry from the 20th level characters I've played in "high level" games, all 18 stats and crazy amounts of magic items. Browsing through some of my old character sheets, it's apparent which ones were started at 1st level and which were written up at a higher level.
I suppose the question here is if it's possible to simulate an organic character development process in order to create some high level characters that aren't patently cookie-cutter. I've used the tables in the DMG before, but haven't really been satisfied with the results; they resemble whatever I'd come up with off the top of my head. When I say cookie-cutter, I mean characters who have +3 swords and +2 platemail and rings of protection. My high level D&D fighter used a +4 club and some +5 chainmail because that was the best stuff he ever found. Apparently, looking at the sheet, he also had a +2 club. No idea where all these clubs came from. That character owned a large dominion at one point, gained during the course of play. I suppose I could create a high level fighter who looks similar, but that land...I remember him smashing a lot of orc skulls to clear it out.
A lot of gamers write extensive backgrounds for their characters, and I've never been a fan of such. In fact, I think it's annoying. But if I'm making a high level character, there has to be some existing background to justify the character's current state. Unlike my fighter above, the character never actually did anything within the game. Surely the character can be treated like an NPC prior to being played as a PC, an existing history referred to when necessary. But again, it's not the same thing. Even a system like Central Casting isn't satisfactory. Playing is a much richer experience vs. writing up something or rolling on tables, and there doesn't seem to be an easy way to duplicate the actual play to create a character that "feels" right. What's the solution?