I got the old magenta basic set from my uncle way back when. Me and the kids from school would play after school (in 6th grade, IIRC), and I was the DM. We had weird names like Dogster, Elfk, Dude, Questor (from Gauntlet) and what not...
It must have been mid-80's when Real Genius and Top Gun were out, because my first character was named Val Kilmer. He was a Fighter, and was dark and fought like Batman. He even had an elf sidekick. It was SO ironic when the 3rd Batman movie came out... I was a decade ahead of myself.
In any case, we picked up the Expert, Companion, Master, and Immortal sets and had a blast. It wasn't until 91 or so when we adopted 2nd edition and statted up a new group of characters (though later, we connected the continuities and had the characters meet).
I've got to say we had the most FUN during 2E. Spelljammer was a HUGE jump and suddenly our characters were out in space. Those two Spelljammer adventures (Goblin's Return and something else) were adventures that we STILL talk about to this day. We used spelljammer as a vehicle to run modules in other campaign settings, and when the mood struck, we'd make new chracters, and add them to the party.
When we finally got around to Dark Sun, we started with new characters again, and after a couple adventures, they were picked up and rescued and added to the cast.
Then came one of the BIGGEST adventures... Dragon Mountain. We had a blast with that. However, since the party was higher in level already, they made it their goal to CLEAN OUT the entire mountain and turned it into a headquarters. There was even a spelljammer dock for the ship.
Good times...
In the end, though, we had so many characters, we had a great event that offed a bunch of them, and the remaining ones went on the Apocalypse Stone adventure. The universe was completely rearranged, and the world was remade.
A select group of characters were all put back to level 1 again for 3E, and had no memory of what happened. As time went on, they alone became aware of the changes around them (they KNEW that halflings used to have hairy feet, and dwarven women had hairy chins, and kobolds didn't used to be reptiles).