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Bandai says that it was released in September 1996 (It was also said that there was no exact release date left.) In summary The answer of title, Pokemon cards printed earliest is the Pokemon card released before Sep 1996
I am also playing Insolent Neonate, which has worked out surprisingly well, though there may be better options out there
(You may cast this card converted for 2B.) Flying Whenever you draw a card, if you're the monarch, target opponent loses 2 life
In the maindeck, you have eight Elves to continue enabling it, even if they end up knocking off your 1/1 token
Theres also the Gyruda, Doom of Depths combo, where youll cast Gyruda, mill some cards, cast one of the clones or shapeshifters youve just milled (preferably ones that ignore the legend rule), effectively copying Gyruda and its ETB trigger