Which game/generation do/did you like the most (as in subjectively enjoy) and which do you rationally think is the best?
In my case, I enjoy playing the first generation the most, probably due to the novelty at the time, and nostalgia nowadays. As for the second point, I can't decide between HG/SS and B2/W2, both due to the sheer amount of content available. You can explore endlessly and do an amazing number of different things, so it can be enjoyable for even more audiences. I couldn't decide because while B2/W2 have more Pokémon species and the competitive online component, HG/SS having two regions, both easier on the eyes than Unova, makes the single-player experience better in my opinion.
I'd love to hear thoughts on both ends. What gives you the nostalgic shivers, and what would you grade A+? Elaborating on the reasons is optional, but makes way for entertaining discussions --- Platinum FC: 2063 1730 8794; HeartGold FC - 0560 9058 5184; Diamond FC - 3179 2247 2864; Black FC - 2279 2860 5022; White FC - 3138 5784 9025
History: Began with Pokémon Red when it was released and has played every main series game since.
I enjoyed Pearl the most. It was completely new graphics, cool sprites, physical/special split, online connectivity, and a way to EV train practically. It was a completely new step that carried us stylistically through Gen V. It is to Gen V what Gen I is to Gen II. It was very fun and I poured hours into it.
Best gameplay-wise easily goes to Black 2. The PWT put it over the top, after already having BW's Global Battling aspect. It had many wonderful cameos and was an overall fun region. The PWT was a great way to wrap up the end of an era (Gen III-V).