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>Gen I & II
I got both versions, plus Yellow and Crystal for each gen. Blue and Gold were the ones I played first of each gen, however. These came out during my late elementary school years, a great time to play some fucking Pokemon!
My first starters were Bulbasaur, and then eventually Cyndaquil.
>Gen III
I stopped playing Pokemon around when I was nearing the end of Jr. High. The loss of the clock mechanic and the fact that the old pokemon weren't transferable to R & S turned me off of the series, if felt like if they were just going to build me up and throw away all the old stuff like that, what was stopping them from doing it again and again? Plus I only had a couple of friends who got them, around that time in my life most of Pokemon's popularity was getting mitigated by the "blech kid stuff is for kids!" mentality that many teenagers get hilariously serious about.
tl;dr, felt betrayed by the series & less of my friends were into it
>Gen IV
It had been a while since I'd played Pokemon. D&P came out during my senior year of high school. I got Diamond because it seemed the less girly of the two names... I was still a teenager (though an older one), so cut me some slack. I had fond memories of playing gens I & II, and I was pleasantly surprised that I had a lot of fun playing this one.
Toxicroak and Infernape were my bros.
I must confess that I couldn't finish HG. Even with all the new bells and whistles the story couldn't keep me hooked enough and playing the game became a chore.
>Gen V
I chose the Gen by the flip of a coin. After the fact I'll say that I'm glad that I got White version, Zekrom is a badass. I haven't had a lot of money to spend for awhile, so I never got around to buying B2 or W2.
Leavanny, Haxorus and Carracosta are my favorites from this gen. I'm running my second playthrough only now, and I have to say I understand why a lot of people love the hell out of Archeops too.
