Christmas of 1999 my parents got me my first ever gaming console, a Playstation, and the game Spyro the Dragon to go along with it. For the next couple of months my dad and I took turns constantly playing. I would sit there watching him play his game when he was home and when he was at work I would play under my own game. It was always fun watching him play because he was always a level or two ahead of me, so I could always just memorize what I would be coming up against in the upcoming levels.
Then we reached this one level called Tree Tops, and one thing that you had to do was use these speed power ups to reach an island far in the distance. We tried over and over again to reach the island, trying different paths, all to no avail. Finally, one day as my dad was at work, I was sitting on the floor in front of the T.V. trying to find something that we could've missed that would help us. As I was walking the paths (instead of using the run power-ups), I found a path way that we always ran by but never thought it was any help. I decided to take that way and found that it was in fact what we needed to reach that island.
I was so excited that I decided to call my dad at work and let him know that I figured out how to beat the level. After telling him how I did it he told me that I was "grounded" from video games for the rest of the day, because I wasn't allowed to bypass him in the game.
That is one of my favorite and earliest memories of playing video games.