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As a first-time play-through, any of the gen iv or gen v games. As something that's replayed over and over again, XY are incredibly easy to get through for me without feeling like a chore.
Gen 3 for me! I though Hoenn got the balance between new and familiar Pokemon while still having a reasonable sized pokedex. Something only Gen 3 and 4 achieved in my opinion. Mightyena is one of my favourite pokemon and so enjoyed it's introduction as well.
Meanwhile Gen 1 has a special place in my heart, I replayed the originals so many times that when they released the re-makes I bought them on day of release and they lived up to every expectation. I'm gutted that my internal memory on all of them has now died and yet there has been no online release :(.
Gen V was the best for me, this was the time that i got into the Pokemon games, and i didn't even knew Pokemon franchise started as a video game before it became an a franchise and multi-million dollar worldwide popular series.
Gen 3, because RSE has a great storyline and some great soundtracks to go with it. Only real downside to Gen 3 is the lack of the Physical/Special split between moves, as that was first introduced in Gen 4.