It’s gotta be the Primeape from Jungle for me. I remember being so happy I had just gotten a bunch of base set cards from some packs my parents bought me, and I ran down the street to my buddy’s house, only for him to show off some new Jungle stuff. He showed me his Primeape and I thought it was such a cool card, I think I traded like 3 non-holo rares for it (yes, probably not my best negotiation 
one was a Dugtrio, don’t remember the other two). It was also the first card I ever actually traded for, and I still have it in my personal collection binder 
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