I'd say as far as overall content goes, Heartgold and Soulsilver. It took me right around 55 hours to beat the game (truly beat it). Being able to explore two regions is absolutely incredible. It makes me wonder why they haven't done it again. It also has the best soundtrack in the series, both the old 8 bit tunes and the modern updates.
I'm hesitant to say X and Y simply because it relies so much on old Pokemon. Say what you will about gen 5, at least it presented the new Pokemon as the focus, at least in B/W 1. Granted, X and Y pretty much objectively have the best gameplay, but the lack of new Pokemon really hurt it for me. It's still a great game, but only 70 new ones? That's disappointing. And, if you don't get into the meta game, it doesn't seem to have much to offer. Three legendaries to catch, barely any side quests (besides Looker) and not much to explore, either.
I'd say all the games in the series are great in their own ways though (besides the original Red and Blue. Those games were literally obsolete the moment G/S/Cr came out).
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