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>Gen 1
Great games, short but simple. There are inherent oversights and design flaws, but I give it a pass. Overall a good kickoff.
>Gen 2
The best generation. Two regions, moving sprites, shinies, a day and night cycle, BEAUTIFUL sprites to boot, and a short and sweet story. Sad there was not that much post-game, however. If only the mobile-trade system was ported to the western releases. Oh well at least it's fun to tinker around with it on emulators.
>Gen 3
Spectacular as well. Sad that there was no backwards-compatability, but the remakes saved that aspect. Great remakes, awesome music, and cool designs everywhere. I liked Hoenn and its island vibe alot, and while most people don't like the Sevii Islands I enjoyed them a lot and FRLG's postgame was awesome too. Not to mention RSE's contests and the awesome battle frontier.
>Gen 4
The last generation where I could feel that it's Pokemon. Awesome story, I loved the lore and all the music. DS stuff was revolutionary, Wi-Fi was awesome and I'm glad they brought contests back for round 2 on it. All of the events and Wi-Fi activities at the time were great, and the legendary Pokemon were awesome too. HGSS were awesome, Pokemon that follow behind you, all that shit was awesome. I loved the spiky eared Pichu event and the whole Silver is Giovanni's son was fucking awesome and the whole game itself was a great ride back to Gen 2, and in style too.