Probably the first time I saw the opening cutscene in FF7. I remember my friend had a PS1 for a while but all he had was racing games and demo disks (remember those lol) but one day his dad brought home ff7 and it was early afternoon. We slapped that baby in and it was the first time a game ever "wowed" me lol me and my friend took turns playing that for the next 8 hours right up until we got out of midgar. I went home and begged my dad for months to get me a PS1 after that lol Good times.
My parent bought me Life Force for Nintendo on my 10 b'day and hide it in my closet, but i found out before dinner and rush back to my room. didnt get to eat my cake or dinner that night.
Play the hell out of landstalker (1992/1993) trying to get 100% exploration, but was never able to do it; until recently (2012) when i was playing on an emulator, i accidently drop into a cave hidden within the bushes that i never knew existed and i have walk through that area millions of time before. The orical stone finally say that i have explore 99% of the games after that :D
i was playing fable 2, trying to get a present from a monk. I did everything i could to max out his like level, but he still refuse. So i take him outside of town (was trying to keep my good side intact) blow his head off, but found nothing. I chased after his head that was rolling down the hill trying to kick it out of spite, and unfortunately got caught by a guard and was force to pay a fine or get band. I payed the dam fine and walk back into town doing my hero things like usual and sign auto graph for children. Suddenly one of the little girl ask me why i killed that man? I was literally shock that fable 2 NPC interaction can be much deeper than i though. Ever since, i just play around with the NPC and pay close attention to everything that they say or do. I found so much more shocking things about them and it made me wonder, can Milo experiment actually based on the NPC interaction from Fable 2? Of course, you will only see these kind of NPC realism if u play as a good person i guess or else they will just ignore you.
I don't know about anytime of the year memories, but as far as Holiday Videogame memories, I received LOTR The Third Age for Christmas one year, and I don't remember why but we didn't really have anything planned for the holiday that year and I played that game almost the ENTIRE day.
Anytime I hear of or see that game I think of Christmas haha.