Second edition AD&D was the first D&D that I had experience with. I think I was twelve or thirteen at the time. A friend of my sister ran a bizarre game that made no sense to me at the time. It involved some sort of dark elves killing a lot of weird guys who wanted to suck out your brains and had tentacles on their face. Little did I know at the time the guy running the game was essentially writing his own Drizzt fan fiction. It's not surprising to me now. After all, the kid was 14, R.A. Salvatore's prime demo range.
The game was filled with exactly what you would expect. The DM had his own character that he was using as an NPC, and his character was always the best. The hordes of monsters were there to be slain by him and to make us look awful. There was no such thing as treasure, there was no experience to be had, and the story line seemed to consist of the Dark Elf trilogy. At the end of the session all he said was, "Ok, you level up".
That's how I thought D&D was supposed to be run. I didn't know any better. Dice seemed like a strange thing that you didn't really need to use. You just told the DM what you wanted to do and he decided, arbitrarily what it is you actually did. The DM was supposed to make up a super hero to save everyone and you had paper in front of you to keep track of your hit points. You had weird stats that seemed to make little or no sense as the DM had a screen and would roll some die and say "Ok, you take X much damage" where X was inevitably enough for you to fall unconscious and be saved after some Dance of Death inspired battle shenanigans. After the death and destruction, you went up a level. Experience didn't seem to matter, after all, you just went up a level every time you played. I was told to be a half-elf, because they were always the best. However, you should be half-dark elf. It made sense enough to me.
Somewhere in the mix was a firbolg. Why a firbolg? I really have no idea what a firbolg was doing in the Underdark. I've read edition after edition of Underdark flavor texts and backgrounds. Mushrooms that scream, mindflayers, cavefishers, goblins, duergar, demons, you name it. No firbolgs though. Maybe he was hanging out in some hitherto unknown mushroom forest. Maybe he was half-dark elf. I still have no clue.
My second experience wasn't much better. I played with another group of my sister's friends, all still a few years older than me. It was based in Dragonlance, another setting in which I had no frame of reference. Someone in the party was a mage with silver skin and diamond pupils, really. I was a warrior with dragonscale armor and a shield that protected me from dragonbreath. Also really. I was maybe 13 at the time. The adventures were pretty much exactly ripped from what I later learned to be the Dragonlance Chronicles. Again, no big shocker.
So the question really is, why did I stick with it? I loved the books. I loved reading the books and looking at the art work and learning the rules. I learned that the people I played with had no idea what they were doing. They weren't really playing D&D, they were playing some homebrew rules set vaguely based on D&D properties. I still had a great time, and homebrew rules are a great edition to the game, but it was an early teen game after all. When I started running my own game when I was 15, I began to use the actual rules. I had two or three people I played with, and it was a great way to waste some time. The characters were a little more unique and a lot less stolen. The game took place in established worlds, but didn't borrow any literary characters. The ideas, while not wholly original, were at least not blatant rips offs. I started playing in games run by others my age that were the same way. I played in the forgotten and cast off Red Steel setting and loved it. What the fuck is cinnabar?
So that happened until I went to college, met people who played D&D as well, some of whom had played it for years and learned how fully awesome the game could be. Somewhere around my sophomore year, 3rd edition came out. I loved it immediately. It was much faster and simpler than 2nd. It was much easier to understand and the stories seemed to be easier to be told. The only problem? Most of the settings went away! New settings were introduced and more were updated, but some of my favorites missed the cut. Chief among them, Planescape got the axe. I understand why it did now, but it still hurts. Mostly because Planescape had the best art and it had Torment. No other setting comes close to my love for this one.
The upshot was that by the time I had almost graduated I was playing in several games, all of which had their own worlds and settings. All of the stories were robust and rich, though many were dark and putrid in their own right. The game that I was playing now was nothing like the game I was playing then. It was still great fun, and it's continued to be fun in the years since. I've made the transition to 4th now, and I love it. I consider 4th to be a great basis to build a story around, and boy do I love the skill checks and skill challenges that have arisen. I find them fascinating.
I still remember playing in a game for the first time with people who had written and published gaming supplements for their own for various companies and remembering those first games I played. The only thing I remember thinking was, "Wait, it's not actually like that?" and being filled with excitement as I realized what tabletop roleplaying could actually be.