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When I consider which gen was the best, I consider how much I loved playing it when it came out. Of course gen I and II are shit now, They're over a decade old!
I loved Gen II because it introduced genders, held items, better graphics, shinies, and you got to go back and beat Kanto again.
When I was a kid and I fought Red on top of Mt. Silver, I knew no game would ever be better.