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From the How to Train Your Dragon movies:
Movie Hiccup:
-Noivern- I had a hard time choosing a dragon type to represent Toothless so I ended up choosing two Pokemon to represent him. The first is Noivern because I feel that's the closest Dragon-type Pokemon has to a Night Fury.
-Goodra- The second Pokemon I chose to represent Toothless is Goodra because not only does Goodra's personality fit Toothless but it's face is pretty reminiscent of Toothless especially its large green eyes.
-Skitty- Toothless is very heavily inspired in design by a cat and his mannerisms heavily take after a playful kitten.
-Klingklang- To represent Hiccup's inventor side.
-Dragonair- To represent Valka and how Hiccup prefers to be a peacekeeper between dragons and vikings.
-Coballion- I just feel like this Pokemon represents leadership and the responsibility chieftainship holds very well.
Astrid:
-Altaria- Altaria is a beautiful blue Dragon type like a Deadly Nadder is a beautiful blue dragon.
-Crobat- Deadly Nadders are supposed to be one of the swiftest dragon species and the swiftest regular Flying type is Crobat. It is also part Poison type and Nadders can shoot poisonous spikes from their tails.
-Growlithe- Stormfly's personality and mannerisms definitely take after a dog and I consider Growlithe the perfect mix of loyal and playful. It can also breathe fire.
-Aegislash- A perfect Pokemon for a strong viking warrior.
-Escavalier- It looks like an axe.
And then the book series.
Book Hiccup:
-Vibrava- In the book series, Hiccup has a small, green dragon named Toothless. Vibrava represents Toothless' size perfectly and kind of matches Toothless' color scheme.
-Magikarp>Gyarados- Hiccup is an underdog and in the books, he is often referred to the nickname "Hiccup the Useless" or just "Useless". The books also have an overarching theme about becoming a hero the hard way and no Pokemon embodies that more than the Magikarp line.
-Alakazam- If there's one thing the books emphasize, Hiccup may not be the biggest or strongest viking in the world but he is the smartest. Just like Hiccup, Alakazam would be able to analyze a situation and think up a plan fast. It would also provide a fiendish amount of luck.
-Honedge- Hiccup is an excellent swordfighter in the books. As this Pokemon would appear with pretty much every other viking, each of them have differences in size and appearance. Hiccup's Honedge would be a lot like his sword in the books, kind of small, a little rusty along the edges, and has the motif of a dragon's tail along it's blade.
-Drampa- Hiccup has a second dragon called the Windwalker in the books. Drampa looks the closest to it and has its personality.
-Kingdra-
Kingdra represents what he has accomplished.
Accompanying:
Noivern- In the ninth book, Hiccup meets an old dragon called the Wodensfang.
Like the dragon this Pokemon represents, it is the size of a Noibat due to its old age.
Book Fishlegs:
-Clauncher- To represent the lobster claw necklace Fishlegs has in the books that is his most prized possession.
-Magikarp- Same reason Hiccup has one. However unlike other Magikarp, this one has Rage. This is to reference Fishlegs' Berserk side.
-Sligoo- It looks the closest to Fishlegs' dragon in the books, Horrorcow.
-Buizel- Fishlegs can't swim and since so many viking activities take place at sea, this Pokemon would be very needed.
-Honedge- Sadly the weakest Honedge in the world to reference Fishlegs' sword, Mr. Pointy.
-Hydreigon-
Alvin the Treacherous (Hiccup's archenemy in the books):
-Shuppet- Alvin's whole motivation is based around revenge and Shuppet crave vengeful emotions. At first, he would have one Shuppet around him but as his thirst for vengeance grows throughout the series, more and more would flock around him.
-Aegislash- To represent what is considered to be one of the best and most impressive looking swords in the archipelago, this Aegislash would take after Alvin's sword, big, shiny, and having a lightning motif along it's blade. To reference how Alvin keeps losing limbs throughout the series, this particular one's Defense form gets more and more chipped away until it completely disappears in the final books.
-Bisharp- Not only are these Pokemon said to be merciless while finishing off a target, Bisharp lead groups of Pawniard to do it. This makes this Pokemon perfect for "His Most Mighty Murderousness, Alvin the Treacherous, Great High Chieftain of the Outcast Tribe".
-Garchomp- This was a hard choice because the most prominent dragon that appears with Alvin in the books is an Exterminator, a big, black, panther-like dragon with sword claws at the end of its talons. There's not a Dragon type Pokemon that looks quite like this so I ended up going with Garchomp for being big, having a dark color scheme, and having long claws/fins/scythes on its arms.
-Mismagius- His mother's a witch.
-Kingler-
This particular one has a metal right claw to reference Alvin's hookhand.
Camicazi (Astrid's book counterpart)
-Salandit- Camicazi is a burglar, Salandit is based off a bandit. This one is a female to represent the fact that Camicazi is a heir to an all-female tribe.
-Dratini- To represent her dragon, Stormfly. Stormfly in the books is a very rare, serpentine Mood dragon and Dratini is a rare, sepentine Dragon type.
-Kecleon- Another attribute of Mood dragons is that can change color at whim. Dratini can't do that but Kecleon can.
-Klefki- Camicazi can get into anything.
-Snivy- Camicazi is very smug in the books and Snivy's one of the most smug Pokemon there is.
Movie Hiccup:
-Noivern- I had a hard time choosing a dragon type to represent Toothless so I ended up choosing two Pokemon to represent him. The first is Noivern because I feel that's the closest Dragon-type Pokemon has to a Night Fury.
-Goodra- The second Pokemon I chose to represent Toothless is Goodra because not only does Goodra's personality fit Toothless but it's face is pretty reminiscent of Toothless especially its large green eyes.
-Skitty- Toothless is very heavily inspired in design by a cat and his mannerisms heavily take after a playful kitten.
-Klingklang- To represent Hiccup's inventor side.
-Dragonair- To represent Valka and how Hiccup prefers to be a peacekeeper between dragons and vikings.
-Coballion- I just feel like this Pokemon represents leadership and the responsibility chieftainship holds very well.
Astrid:
-Altaria- Altaria is a beautiful blue Dragon type like a Deadly Nadder is a beautiful blue dragon.
-Crobat- Deadly Nadders are supposed to be one of the swiftest dragon species and the swiftest regular Flying type is Crobat. It is also part Poison type and Nadders can shoot poisonous spikes from their tails.
-Growlithe- Stormfly's personality and mannerisms definitely take after a dog and I consider Growlithe the perfect mix of loyal and playful. It can also breathe fire.
-Aegislash- A perfect Pokemon for a strong viking warrior.
-Escavalier- It looks like an axe.
And then the book series.
Book Hiccup:
-Vibrava- In the book series, Hiccup has a small, green dragon named Toothless. Vibrava represents Toothless' size perfectly and kind of matches Toothless' color scheme.
-Magikarp>Gyarados- Hiccup is an underdog and in the books, he is often referred to the nickname "Hiccup the Useless" or just "Useless". The books also have an overarching theme about becoming a hero the hard way and no Pokemon embodies that more than the Magikarp line.
-Alakazam- If there's one thing the books emphasize, Hiccup may not be the biggest or strongest viking in the world but he is the smartest. Just like Hiccup, Alakazam would be able to analyze a situation and think up a plan fast. It would also provide a fiendish amount of luck.
-Honedge- Hiccup is an excellent swordfighter in the books. As this Pokemon would appear with pretty much every other viking, each of them have differences in size and appearance. Hiccup's Honedge would be a lot like his sword in the books, kind of small, a little rusty along the edges, and has the motif of a dragon's tail along it's blade.
-Drampa- Hiccup has a second dragon called the Windwalker in the books. Drampa looks the closest to it and has its personality.
-Kingdra-
Trying to keep this as simple as I can, in the last four 1/2 books of the series, a Seadragonous Giganticus Maximus named Furious starts a dragon rebellion that seeks to wipe out the human race after years of being enslaved and mistreated by humans and, in Furious' case, a betrayal that resulted in the death of his brother and led to him being locked up for 1,000 years. This starts a war between dragons and humans and later, humans who want the war to end with the dragons going extinct and those that want the war to end with no one going extinct. The only way to end the rebellion is to find the 10 King's Things, the most important being the Dragon Jewel, and get crowned king on the Isle of Tomorrow. Hiccup has already collected eight of them throughout the series and, being passionate about dragons, goes to find the final two. Through several series of events too numerous to recount and great difficulty and loss, he manages to find both items, get to the Isle of Tomorrow, get crowned king, find out how the Dragon Jewel works, and end the war between man and dragon with both species living on peacefully for the rest of his lifetime.
Accompanying:
Noivern- In the ninth book, Hiccup meets an old dragon called the Wodensfang.
t's heavily implied that the movies take place a long time before the books and the Wodensfang is supposed to be a version of movie Toothless.
Book Fishlegs:
-Clauncher- To represent the lobster claw necklace Fishlegs has in the books that is his most prized possession.
-Magikarp- Same reason Hiccup has one. However unlike other Magikarp, this one has Rage. This is to reference Fishlegs' Berserk side.
-Sligoo- It looks the closest to Fishlegs' dragon in the books, Horrorcow.
-Buizel- Fishlegs can't swim and since so many viking activities take place at sea, this Pokemon would be very needed.
-Honedge- Sadly the weakest Honedge in the world to reference Fishlegs' sword, Mr. Pointy.
-Hydreigon-
During the 10th book, they meet a Triple Headed Deadly Shadow dragon that belonged to Fishlegs' mother which becomes Fishlegs' main dragon for the rest of the series.
Alvin the Treacherous (Hiccup's archenemy in the books):
-Shuppet- Alvin's whole motivation is based around revenge and Shuppet crave vengeful emotions. At first, he would have one Shuppet around him but as his thirst for vengeance grows throughout the series, more and more would flock around him.
-Aegislash- To represent what is considered to be one of the best and most impressive looking swords in the archipelago, this Aegislash would take after Alvin's sword, big, shiny, and having a lightning motif along it's blade. To reference how Alvin keeps losing limbs throughout the series, this particular one's Defense form gets more and more chipped away until it completely disappears in the final books.
-Bisharp- Not only are these Pokemon said to be merciless while finishing off a target, Bisharp lead groups of Pawniard to do it. This makes this Pokemon perfect for "His Most Mighty Murderousness, Alvin the Treacherous, Great High Chieftain of the Outcast Tribe".
-Garchomp- This was a hard choice because the most prominent dragon that appears with Alvin in the books is an Exterminator, a big, black, panther-like dragon with sword claws at the end of its talons. There's not a Dragon type Pokemon that looks quite like this so I ended up going with Garchomp for being big, having a dark color scheme, and having long claws/fins/scythes on its arms.
-Mismagius- His mother's a witch.
-Kingler-
When it is first realized that one of the things that has to happen to end the rebellion is to become king, the vikings' first course of action is to have a swordfighting competition to decide who should collect the items and become the next king. Initially Hiccup wins the competition but after a secret is revealed that gets him thrown into exile, Alvin becomes king of the Wilderwest for the 10th book and stays as a contestor for king for the rest of the series.
Camicazi (Astrid's book counterpart)
-Salandit- Camicazi is a burglar, Salandit is based off a bandit. This one is a female to represent the fact that Camicazi is a heir to an all-female tribe.
-Dratini- To represent her dragon, Stormfly. Stormfly in the books is a very rare, serpentine Mood dragon and Dratini is a rare, sepentine Dragon type.
-Kecleon- Another attribute of Mood dragons is that can change color at whim. Dratini can't do that but Kecleon can.
-Klefki- Camicazi can get into anything.
-Snivy- Camicazi is very smug in the books and Snivy's one of the most smug Pokemon there is.
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