When it comes to video games, there are just too many to type up for me to put into this response. Here are a couple of classic ones though:
1.) The first time I played a video game system: This was around 1994 when my brother got an SNES for his birthday. I didn't even know what the thing was, but that night when he got it I remember playing Super Mario World and Aladdin. I was soo bad at playing that it took a good week to beat the beginning stages of both games..
2.) Madden 99 PS1: In the summer of 1999 I had a good time. I would play recreation baseball during the evening hours. Later on at night I would watch DBZ at 12:30 AM during the midnight run, and then afterward play 2 games of Madden on franchise mode after my parents fell asleep watching the living room t.v. When watching DBZ it was my first time watching the Sayin and Namek Sagas; therefore it was cool watching these classics without the sense of what was going to happen. Madden 99 was also epic, for I went 13-3 in a season using the Lions and then won the Superbowl against the Seattle Seahawks 9-7 (Seattle was in the AFC back then).
3.) The most obvious: Playing Smash 64 and Melee in 1999/early 2000's. Epic matches, 99 stocks, and all that jazz.