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(#1) Charizard
- Fictional Character
How Much It's Worth: Up to $11,999
Why It's Worth So Much: Error cards are some the most valuable of all Pokémon cards, and some of the holographic base sets have a rare error. These cards, known as "Shadowless," are noticeably missing a shadow to the right of the image.
This error was remedied rather quickly, so not many of these cards exist. Couple that with the fact a holographic Charizard was every kid's dream, and you've got a pretty darn valuable piece of paper in your hands.
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(#2) Pikachu Illustrator
How Much It's Worth: Up to $195,000
Why It's Worth So Much: This card was given only to winners of the CoroCoro Comic Illustration Contest in January 1998. Only 20 to 39 of these cards exist in the world and only 10 are in mint condition. As of October 2019, this celebration of Pokémon art the most expensive Pokémon card ever sold.
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(#3) Mewtwo
- Fictional Character
How Much It's Worth: Up To $1500
Why It's Worth So Much: Mewtwo, despite having DNA that contained "the genetic codes of all Pokémon," was one of rarest Pokémon you could capture in the games, and that fact made the critter's card worth a whole lot. While Mewtwo was massively coveted in 1999, the base set shadowless first edition holographic card is exceedingly rare today.
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(#4) Shining Charizard
How Much It's Worth: Up to $3,500
Why It's Worth So Much: Shining Charizard marks the first time a "shiny" Pokémon was found in the card game. The Pokémon itself is holographic, instead of the background, and it's worth even more if it has a first edition marking outside the bottom left of the image.
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(#5) Blastoise
- Fictional Character
How Much It's Worth: Up to $1,500
Why It's Worth So Much: Like every first edition shadowless base set holographic starter, Blastoise was extra rare in 1999, but it's even more coveted now. You'd be lucky if you find a PSA 9 card for less than $700.
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(#6) Raichu
- Fictional Character
How Much It's Worth: Up to $10,000
Why It's Worth So Much: Though it's never been confirmed by Wizards of the Coast (the company that manufactures Pokémon cards), it's thought that just 10 Prerelease Raichu cards exist. The term "prerelease" was allegedly stamped on the base set card and given out only to employees, friends, and family.
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(#7) Black Triangle Error Booster Box
How Much It's Worth: Up to $8,700 for an entire sealed box
Why It's Worth So Much: Old booster boxes regularly sell for thousands on eBay because you don't know the kind of rare cards they might have. A triangle error booster pack is the single most valuable, and a box full of these runs for enough to buy a used car.
They were created when the factory was supposed to stop printing "first edition" booster packs but didn't. Instead, they covered the "first edition" symbol with a black triangle. The factory printed the mistake cards for only a few hours.
These cards are worth something only if they're inside the booster pack (about $250). When they're in a sealed booster box, however, they're worth even more.
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(#8) Pikachu
- Fictional Character
How Much It's Worth: It's so rare you can't find it on eBay. The price is largely unknown, but it's sure to be exorbitant.
Why It's Worth So Much: No. 1, No. 2 and No. 3 trainer cards are always rare. They're only handed out to winners at official Trading Card Game world championships. This adorable, holographic Pikachu card was only given to four winners of the very first Japanese Pokémon Card Game Official Tournament; therefore it's the rarest.
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(#9) Venusaur
- Fictional Character
How Much It's Worth: Up to $6,500
Why It' Worth So Much: Like many of the most valuable Pokémon cards, Venusaur was the main prize in its own base set. In the '90s, a regular Venusaur was hard to come by through trading because of its sheer popularity - but a holographic Venusaur was even rarer (who'd want to give that up?). Today, a holographic first edition base-set Venusaur without a shadow around the image box is the most coveted.
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(#10) Espeon
- Fictional Character
How Much It's Worth: Nearly $3,500 for a PSA 10
Why It's Worth So Much: Gold Star cards were first introduced in the EX line of play. They depict the shiny version of the Pokémon. In the games, these Pokémon had a slightly different coloring from their common counterparts.
Out of all the shiny variants, Espeon is the most valuable because it was distributed by the Pokémon Players Club and given only to people who met certain criteria at events.
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(#11) Master Key Prize Card
How Much It's Worth: Up to $8,799.96
Why It's Worth So Much: There are only 34 copies of the Master's Key Prize Card in existence, as it was only given out during a 2010 trading card game tournament in Japan.
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(#12) Black Star Movie Promotional Cards With Inverse Stamp Error
How Much It's Worth: Up to $800
Why It's Worth So Much: An error always make for the rarest Pokémon cards. Though the promotional cards from the first Pokémon movie aren't worth much, about 120 cards were printed with the logo accidentally upside down on the bottom left corner of the card.
There are just 30 error cards for each Pokémon, including Dragonite, Pikachu, and Mewtwo.
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(#13) Parent/Child Holographic Kangaskhan
How Much It's Worth: As little as $1,500, but ones have been known to sell for thousands more
Why It's Worth So Much: This card was released only in Japan during the Parent/Child Mega Battle Tournament in 1998, awarded to parent-children teams who had a certain number of wins. The Pokéball set symbol on the right is used on the rarest Pokémon cards, so this one can definitely fetch you thousands.
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(#14) Magikarp
- Fictional Character
How Much It's Worth: Between $2,000 and $4,000
Why It's Worth So Much: Though Magikarp is largely known as the worst Pokémon in the game and a useless side character in the anime, only 30 to 100 of these cards exist. This card was given to top qualifying players on the second day of a 1998 Pokémon conference in Osaka, Japan.
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(#15) Machamp
- Fictional Character
How Much It's Worth: Some sellers are trying to sell a shadowless holographic Machamp for $5,000, but that's exorbitant. It typically goes for between $100 and $850 depending on quality.
Why It's Worth So Much: This card was one of the rarest in the original trading card game. Don't be fooled though - these cards are essentially worthless if they've got a shadow to the right of the image box.
Over a million shadowed cards were printed with the first edition stamp. The shadowless version is still rare and carries a hefty price tag.
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(#16) Pokémon Snap Cards
How Much It's Worth: It's hard to tell the exact value because these cards are exceedingly rare, but they have allegedly sold for $8,000 according to Kotaku.
Why It's Worth So Much: Nintendo ran a promotion for their now-forgotten 1999 N64 game Pokémon Snap. They invited players to send their best in-game Pokémon photos to a Japanese magazine, and the best shots were transformed into trading cards.
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(#17) Tropical Mega Battle Cards
How Much It's Worth: The price is hard to nail down, but a single PSA 10 card has been known to sell for $5,000.
Why It's Worth So Much: These rare cards were available only at a 1999 trainer event in Hawaii.
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(#18) Chansey
- Fictional Character
How Much It's Worth: Up to $1,000, but commonly between $200 and $500
Why It's Worth So Much: If you happen to nab a first edition shadowless Chansey, you've got your hands on one of the rarest Pokémon cards in the original trading card game. Even if normal Pokémon are the second-most common in the game, this particular card was available only in the original 1999 base sets.
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