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Honestly the most memorable moment was fighting Red on Mt. Silver. Just working your way up the mountain fresh off of beating the Elite Four thinking you're the greatest trainer in the world. Not knowing what to expect, you reach the top of that fucking mountain. You see the sprite and you're in disbelief because you vaguely remember seeing it before
>". . .. . ."
>". . .. . ."
In your excitement and confusion he proceeds to stomp your entire team.
I honestly feel for the newer generation of players that they never get to experience this moment unbiased and fresh because the older generation talks on and on about it. We had no Internet, no guides, everything was learned either by word of mouth or fumbling around which led to amazing moments of discovery.