I always chalked up the overwhelming strength of Pokemon Gen 1 to be a lightning in a bottle situation. The marketing push from '98-'00 went harder than I've ever seen in my entire life. The anime had a perfect after school time slot, and was the first serialized anime for most millenials. The Game Boy game was the first massive portable RPG most people had ever played - there really weren't many RPGs at all on the Game Boy. And the trading card game, man, you couldn't get away from that in school at the time.
But then by the time Gen 2 rolled around, my casual friends IRL didn't bother, and I ended up quietly playing Pokemon (((Silver))) by myself. It was just seen as a dead fad by 2001. Even from my PoV, nothing newer particularly stood out as iconic beyond Gen 1. There are a few Pokemon here and there that I liked, but it's sort of akin to being really into a band for a time, and finding yourself entranced in a particular era - when the band was good - and then you try and listen to their newer albums, and you come away with a couple of songs that you could fit into your playlist, but otherwise, you stick to their classics.
It's kinda funny - in my head, when I try to think of newer Pokemon I like, I immediately go to Rayquaza:
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and that is a Pokemon who debuted nearly 20 years ago.
There's definitely something to be said about Gen 1 and the rest of Pokemon feeling like two different franchises altogether. It's the same sort of thing with the Star Wars trilogies, only, Pokemon never had such a clear line-in-the-sand drawn with contention between fanbases. There's a weird hostility from modern Pokemon fans calling others "genwunners" disparagingly, and then then genwunners don't give a shit, because they just wanna enjoy their nostalgia over something they enjoyed when they were 9-year-olds.
Kinda makes sense that it turned out like that: the people who complain about genwunners are too autistic to understand that Pokemon's just a nostalgia thing to a lot of people, not a way of life.
oh and we apparently have a thread about pokemon generation elitists, and Null closed it because he is a genwunner lol
https://kiwifarms.net/threads/pokemon-generation-elitists.29770/post-2176901