1987, I was 10 years old (5th grade), and the game was Avalon Hill's Lords of Creation. My early gaming consisted mainly of making equipment lists and winging things, generally with one player. I played some OD&D in 87/88.
I started gaming seriously in 1989 (with 2e), still generally with one player, and I was the DM until I reached high school. Since then I've played more, but still primarily DM.
I remain at my best when winging it, and I love equipment lists.
Probably around 85-86 with the red box... Was 10 or so at the time... And i had just 1 (good) friend (with whom i still play today). He had to make and play 4 characters at a time!