The first character I ever leveled from low level to high level ... 2nd ed. D&D in 2000-02. Yes we were sort of behind the times, clinging to 2nd ed. right as 3rd was coming out. No one knew what OSR was back then, but we were practicing our own brand.
Barak the dwarven cleric was the characters name, a follower of Moradin and a paragon of wisdom and virtue (well at least in the beginning). It was actually during the second time around with D&D for me. To explain what that means, I left D&D in middle school and didn't really come back to it until my mid 20s. My first experience with D&D as an adult was a second edition game. I had been wargaming with a club in Las Vegas (the Las Vegas Gamers Club, LVGC) for a few years when one day a friend struck up conversation about D&D. Well several of us were there and before we knew it we were talking about forming up a game. He offered to run the game for us and next thing we knew ... every Saturday from noon to about 2 AM at my place was devoted to D&D.
My wife frequently worked on the weekends, we had no kids yet and loads of disposable income. So we were leasing this gorgeous 4,000 square foot house. I had a titanic game room. The DM just opened it up to anyone who wanted to play. So we had and your going to gasp here ... TWELVE ... players for a time and rarely below eight players. I can tell you as someone who has DM'd games, played in probably something like 50 games now run by dozens of DMs (many at conventions admittedly but still) that I would never play in nor run a game at over six players and six is pushing it. So how the hell that twelve player game worked I don't know.
The only thing I can say is it was a group of people who felt so nostalgic about the game. We were all caught up in that so much I think it just was one of those once in a blue moon kind of things. The rule was no table-talk/meta talk and absolutely no sideline BSing. We were supposed to keep things in character whenever possible. We had a 30 minute period for housekeeping stuff with the DM at the beginning of the game and that was it. The sessions did go long, but for such a big party we seemed to get a lot done. We faithfully played every week for the better part of two years and I legitimately leveled from one to fourteen with little to no DM fudging on exp, etc. Our exp was chopped up pretty heavily due to the large party size, yet our large party allowed us to take on some pretty powerful encounters that would have been beyond our level otherwise. One other player hit 14 but everyone else in the group lost at least one character along the way.
So over several weeks Barak began to behave strangely. He had a new amulet (disguised his true alignment) with a strange symbol on it. I didn't play that up but it was sort of a case of hiding in plain sight. The party went on for a few months and slowly I was weaving a plan of vile deceit with the DM nudging me along. I felt bad, but it was hilarious fun as well. Anyway long story short I staged a coup d'etat in my home hold, seized control from my elder brother had him and my entire family imprisoned as well as the party. They were all so betrayed and actually angry. It was a moment of triumph and tragedy. The campaign went on for a few more weeks after that, they escaped, raised an army and met my forces (who fought along side the lich) and the forces of good barely prevailed.
We all had a blast and vowed to play again, but somehow we never did re-form that group. We splintered off into other groups over the years and honestly I've lost contact with them all. I live in a different state, etc.
I'll always remember the game though. I don't think it was even in my own top ten in terms of quality, but the level of fun and excitement each week makes it as memorable as they come for me anyway.