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Probably the games during pokemania.
Honestly, it's hard to remember exactly what was first because pokemania was EVERYWHERE. There was the movie, there were toys like the pokedex, there were the trading cards, there was that Pokemon Master Trainer boardgame, people dressed up as pikachu for halloween, it was on the news, Time Magazine had pokemon on their cover, our public library had giant pokemon decorations, everything was pokemon, you couldn't escape it.
Gen 2 felt like a continuation of Pokemania, Gen 3 was cool and I liked the little details like the interviews but I was moving on from the games. I played Gen 4 in high school, but that was from an older perspective, which in retrospect was the perfect game for me given the larger dungeons and online play. Gen 5 was the first time I went to /vp/ to get leaks of the japanese version. Gen 6 I played, beat it easily and went, "yeah, I'm done with pokemon." I came back recently out of curiosity and wanting to try out some of the romhacks. I haven't played an official pokemon game since Gen 6, so here I am now.