A friend of mine in 4th grade had a bunch of books and I loved the pictures. I kept pestering him about them and asking to borrow books.
I got a 1st ed AD&D Monster Manual from a comic and games shop on vacation soon after. That was my first dive into the rules and setting of D&D.
I got whatever edition of the red box came out around then (levels 1-5, elf was a class, still probably my favorite D&D rulebook because it does so much in such little space). Playing was sporadic, getting friends or family to play single sessions here and there.
I never got gaming regular until my friends and I got into White Wolf (mostly Werewolf: the Apocalypse) in high school. D&D 3rd edition came out in college and then it was easy enough to convert everyone.
I've owned a huge number of games over the years (and even played a few of them). Lately I'm very much in "rules-lite" mode. I want to sit down and play, not waste time on character creation or looking up mechanics. I've played a little bit of Dungeon World and want to sink my teeth into more of that.