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I first played Silver. Gen 2 is my favourite, because it is deeply tied to many of my best childhood memories. Playing in the back of a dark car, discovering caves back when the only spoiler could come from printed guides, swimming in deep water and finding a huge guardian of the sea... and all the invented legends we spread as children
Gen 3 is still dear to me, but was for me a way to cope from problems in life, so I don't get the same carefree feelings as hearing Newbark Town's or Olivine's theme.
I was the first of my friends to find Rayquaza in Ruby, boy what sweet feeling to awaken Registeel after wondering what was hidden near my secret base.
I cut before gen 4's release because the legendaries seemed dumb and uninspired; playing it as a grown up it has left me good memories, and great starters.
Gen 5 was really fun to play, I'd argue it found a great balance between exploration and battle feel, introduced some great pokèmon, probably the first time I did a playthrough without keeping the starter.
Haven't played anything later.
