IMO the best Pokemon cards by far are those that tell compelling stories. I tend to dislike cards that feature a Pokemon just standing there with no purpose; they are so boring! The best are definitely those that capture a unique narrative.
A real classic example of this is Shining Gyarados. Just imagine what would be running through that fisherman’s head! He is witnessing quite the surprise monstrosity:

But my personal favorite actually comes from a modern set, Cosmic Eclipse specifically. I really love that FA Pikachu. It’s a card that tells one of the most iconic scenes in all of Pokemon. For those of us who grew up on Pokemon, I think it PERFECTLY captures the imagination of one of our greatest childhood fantasies. I love this card:

What about you folks?
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@quuador that is an amazing post. I never knew about some of these. Thank you.
The Plusle + Minun scene melts my heart.
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You picked my favorite, I think, Red Gyarados.
@quuador posted several of mine, but if I picked some that are perhaps off the radar:
I love the creepiness of this scene. A re-pencil of Aquapolis. Great Encounters Hypno
Or this one, where snubbull is in troubull. How? Why? What next? Skyridge Snubbull
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This is why I lurk on this forum on a daily basis, amazing and all-around positive!
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Ah, that reminds me:
What will happen next for this poor Blizle?
Greetz,
Quuador
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also, i would lose credibility if i didn’t plug this winner at every opportunity

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Well sir, as you insist 

Though, I will shamelessly plug my own collection post, if you want a master list (as complete as I’m aware) of all trainer cameo appearances in Pokémon art in English 
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quibble
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A few that come straight to mind:
Why is this Jolteon caring for a Togepi? Is the Rattata another companion? Are they on a journey? Do they belong to a trainer?

The biggest question from this story is, does Oddish survive?!
And a modern tri-fecta of Mewtwo escaping captivity with the help of Mew, and going on to live a life of annoyance with the little pink fluff ball.
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Dumped Omanyte is probably my favorite!
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nish
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This is what happens when you take too much ketamine

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Open to interpretation whether Chansey has just attacked Aipom or is there to help 
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Love the art from the previous cards in the background.
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Loving this post and idea! This is such an awesome pick-me-up compared to a lot of the other threads posted recently that have been total bummers. I’ve ALWAYS loved the more cutesy Pokemon and illustrations, and especially ones that look as though there’s a story to be told. Here are some of my favorites.

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