Fallout for 10 dollars in 2000, with the left over change I had from buying Age of Empire 2 The conquerors. I was eleven.
I was originally going to buy this stock standard looking rpg named "Deathtrap dungeon" or something because I'd read the choose your own adventure style book it was based on. But when I got my dad's attention (he was carrying my birthday money), it was gone.
Dad grabbed a lone copy of Fallout from the bargain bin and said "This looks really good", to this day, I don't know if it was because he thought it did or because he want to cheer me up.
I didn't play A0E2 for months, I was too busying playing fallout again and again. I hadn't read any manual and the first time through I didn't even know how to spend points I gained leveling up, let alone choose wisely.