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I think my most valuable card (price-wise) is my Gold Star Mew, going for around $100 ungraded last I checked. Pulled it from a booster one Christmas—my first and only Gold Star card. Mew cards are my favorite to collect, so I really lucked out there!
Next to that is probably Ooyama's Pikachu. Wailord ex (Sandstorm) was up there for a while, back when it was tournament legal, but it has dropped considerably since.
I'm curious! Why is the Dewgong the most sentimental one? First card?
Naturally, I can't find the pic I took of my most expensive card and I'm too lazy to take one now. :') But, I'd have to say the most valuable is my misprinted Ninetales. Both for monetary and sentimental reasons.
Spoiler:
Another valuable group are these cards, the Pokemon PLAY 19-21 collection:
Spoiler:
And lastly, pretty much anything from the E-Series is selling for mad money right now.
Probably my Shadowless Charizard in Near Mint condition:
This runs between $500 and $800 right now, I believe.
Next would be my other Charizards from the original Base Set and my Shadowless Blastoise, in Near Mint condition, each worth over $100:
Mind you, these market prices are for ungraded cards. They would likely be worth more after being graded by PSA or Beckett.
Quickly wanted to say that I saw some posters on here saying their cards are worth more than they really are, and I'm guessing they came across the list price of graded, gem mint condition versions of those cards on eBay, which are incredibly rare and expensive. Judging by some of your photos, your cards are not in that good of condition, nor are they graded. Not trying to burst any bubbles, just trying to help!
My mother owns a 1st Edition Charizard that she opened herself when I was just a baby. I get it as soon as I graduate from college (as a present). I'm never selling it.