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Started with Blue on the GBA. I think it was my second game, after Super Mario 64.
Then Yellow, Crystal, Sapphire, Leaf Green, Diamond, Black, Black 2, Emerald, Alpha Sapphire, and Heart Gold, in that order. I don't think I ever got around to playing XY, and I haven't played the latest generation at all.
I also played a lot of Shoddy Battle back when that was a thing, and got ranked pretty highly by using gimmicky teams. My favorite gen is probably 5, but the original games still have a big place in my heart.