Well, the first actual game I played was some DOS based baby game (Yep, even when I was a small child, I have been a computer nerd.
). The first actual video game I played was Pokemon Yellow. Then, my first 3D game was Pokemon Stadium. After that, my first actual PC game was RollerCoaster Tycoon 2. Yep, even when I was a young child, I knew a bit about physics and tycooning...even if I could only beat the first few levels, and at least 10 people died every time I tried to do a scenario.
Pokemon Yellow...I loved that game, and still do. However, to this day, I still have not beaten it. I'm only up to the Elite Four. Before then, I was stuck in Mt. Moon, and when I got it, online guides weren't that common...or accessible to 5-year-olds. I dominated my friends in Pokemon Stadium, and even when I was about 6 or 7, I knew a bit about type advantages, but still believed in the "coolness factor" adjusting types. It is funny watching back in the past me struggling even though now I can beat these games without that much effort, yet still requiring a bit of perseverance.
For the record, the first game I beat was Yoshi's Island for the GBA. I spent weeks on the Bowser battle.