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Did you ever have any Pokemon that you used in EVERY single game? For me, I always picked up a Diglett because I love them to death =D Some Pokes were iffy for me (Rattata, Mankey, Machop, etc...) but I always had Diglett and Pidgey in my party.
I've never played R/B/Y, but in my Crystal version I always choose growlithe because I'm not a fan of Cyndiquill and it's hard to get any other fire types early on. It usually takes me at least half an hour though, because they keep using roar >_<
in the old games i always had pidgeot and arcanine. If i chose a different starter than water in any of them i would always get a gyradros with hyper beam.