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>Gen 1
It lacks a lot of features of later games, and it's pretty imbalanced, but like every other 1st season/book/game/etc, it's still incredibly solid and has a vocal, obnoxious fanbase.
>Gen 2
Directly inferior to Gen 1 in terms of region, level, and world design. Bland, repeats the same story beats with Team Rocket, and the Pokemon and level distribution are baffling. However, the new Pokemon are pretty solid, though obviously worse than the other first 5 good generations, and the amount of content makes it one of the few generations to have more content than the previous one. Despite all its flaws, it still made a lot of good changes, such as held items, Special Split, and the 2 new types
>Gen 3
Due to it being on the GBA, it had an atrocious soundfont. Thoughts on the melodies and composition of the music varies, but it objectively sounds bad when compared to even the Gameboy titles. It also lacked tons of features from Gen 2, like a day/night cycle, and cross-gen transfers of Pokemon. Bar Emerald, one of the best games in the series, it also lacked content. The Pokedex is incredibly solid, but most of the Pokemon in it haven't stood the test of time due to the design philosophy of the time favoring SFMA. This gen also had objectively the best spinoffs, with PMD, Colosseum, and XD. Abilities and EV/IV reworks made it a massive improvement over Gen 2 competitively. FR/LG also makes this the ideal nostalgia-fag gen.
>Gen 4
Weaker Pokedex than average due to the large amount of cross-gen evos/prevos. Physical/Special split was a long time coming and great improvement. Objectively the best competitive scene in Pokemon history. Fantastic games to play through to this day, and Platinum added so much extra content and improved the game that it's hard to rate it anywhere outside the top 3.
>Gen 5
Peak Pokemon. Huge new dex, though inconsistent at times, with some of the coolest Pokemon in the series. Black and White are mediocre, but Black 2 and White 2 are GOAT.