I remember my first playthrough of Gold and while I was in the middle of taking on the Rocket in their Underground Base, I saved my game. However, once I tried to get back on, all of a sudden, it had an error and I could not get back into my game. I was panicking and getting frustrated because I worked so hard to get where I wanted to be and then all of a sudden, this happened.
Another great memory was battling Red for the first time in Gold. I was awestruck because it was almost like battling myself since I played the Gen I games first. The music for this battle was all-time great.
I also had good memories of Pokemon Trading Card Game. I collected Trading Cards back in the day (even getting that holographic Venasaur) and the game was a gateway for me to sorta get invested in competing in the Trading Card scene...which did not go anywhere :P.
Hey You Pikachu! was another great memory, I guess (I was a kid back then :P). I remember repeating so many commands to Pikachu that it kinda got annoying because the reception is not that great.
I have many more great memories, but these stood out more to me.
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