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I started off with gen 3. I was at Gamestop one day with my mum, picking out a new gameboy game. I decided to go for what looked like a zoo simulator or something, and the employee at the counter was like "wait, no, don't pick that one, it's not very good. if you like animal stuff, go for this one" and showed me Sapphire. So I owe it to that one cool gamestop employee.
Favourite so far has to be gen 4. First game that I took seriously, and worked on filling the pokedex as best I could, since I my wifi didn't work with my DS.
I've sunk the most hours into my Y game though, simply because this is the first time I've been able to go online with a pokemon game, and it's opened up so many possibilities now. I finally have a chance at completing the national dex!