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I don't know how I could even rank them. I don't think I can ever think Gen 2 isn't the best purely because of the music. The music was just so wonderful, I'm not a big fan of the remakes because there was this eerie aspect of the old music. No other Pokemon game has made me feel the same, not even Kanto. I guess that's what meant the most to me, even though I know Gen 2 has so many flaws battle-wise.
I'm also a big fan of timeskips, I love seeing how things changed overtime.