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4>2>5>3>1

Since Diamon is my favourite game of all time Gen 4 takes the top spot. Gold and Silver did so much, and are a lot better than the first games. The fifth gen games was really good, but didn't have the same magic as the previous titles, at least not for me. Gen three isn't one I've played too much, although I have beaten Emerald once. Pokemon Blue had it's problems, mainly balancing ones, and it felt aged when I played it (4 years ago). Still a wonderful game, and it deserves credits for what it have done, but it ain't better than the others.

While it didn't sound like it I actually took spin offs into account as well. Doesn't help anyone, I've probably spent close to 1500 hours in gen 4, with gen 2's roughly 150 coming in second place.