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Well, Pokemon isn't a series you need to go through in order. However, you can play Gen 1 via the Gameboy Advance remake Pokemon Fire Red and Leaf Green. My personal favorite is Gold and Silver. For that there is a DS remake you could play on the 3DS via backwards compatibility, Heart Gold and Soul Silver. Also, in G/S you actually get to go to Kanto, the region from Gen 1, after you beat the Joto region. X and Y are also packed with content, have better presentation, and are quite accessible and bring neat additions like avatar customization and such. Those are my three recommendations for you.