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When Hiccup regains consciousness, he finds that he though he was saved by Toothless, he lost his foot. The two have now both lost something. However, Gobber, Hiccup's teacher, had made him a fake foot, which fit perfectly in Toothless's saddle. The Vikings and dragons are living in harmony, and have even become friends, thanks to Hiccup, Toothless, and their friends.

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Once the fire dies out, Hiccup's father goes searching for his son through the wreckage. He finds Toothless, who had wrapped Hiccup in his wings to shield him from the deadly fire. The Vikings go home with the two heroes; Toothless has earned their respect, and they are thankful that he saved Hiccup.

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Hiccup and his friends battle the evil dragon, giving the Vikings a chance to escape. Hiccup's father frees Toothless so that Toothless doesn't get die on the ship. Hiccup and Toothless join the fight. Eventually, they are the only ones left who can stop the monster, so they draw it into the sky, but then trick into crashing into the ground. Because its mouth was full of fire, there is a huge explosion. Hiccup falls off Toothless's back into the fire.

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Hiccup gathers his friends from dragon fighting class and introduces them to dragons that they can ride. They learn to respect dragons, and that they are intelligent creatures that don't just kill because they feel like it. Then the group flies off on their new dragons to help the rest of the Vikings before they get annihilated by the giant dragon, the Red Death.

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After the Viking ships fade into the distance, Astrid confronts Hiccup. She asks him why he didn't kill Toothless and he is frustrated with himself. Then he answers her question: Toothless reminded him of himself. Astrid then told him that she knew he could come up with a plan. Hiccup gets and idea and Astrid supports him.

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Hiccup becomes friends with the Night Fury, who he named Toothless, and works hard to help Toothless fly again with Hiccup on his back. Using the things that he learned about dragons from Toothless, Hiccup becomes very popular for "defeating" all the dragons during dragon school. However, one day, he is discovered by Astrid, his main competitor in class. To prove that what he is doing is right, Hiccup takes Astrid on a flight with Toothless, who can then fly because of one of Hiccup's inventions. Unwillingly, Toothless takes the two new friends to the dragon island where a giant dragon is forcing the other dragons to bring it food. During Hiccup's final dragon fight, Toothless comes to rescue him, after things go wrong. Hiccup accidently reveals that Toothless knows where the dragon island is and Hiccup's father sets out to destroy it, not listening to Hiccup's pleas and warnings.

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Hiccup's father, the chief, decides that Hiccup must go to dragon fighting school for his own good. Hiccup attempted to tell him that he couldn't kill dragons, but his father misunderstood him and the next day, Hiccup started dragon training. He wasn't any good, and his classmates laughed at him. Afterwards, he went into the forest and found the Night Fury trapped in a hollow, unable to fly, though it wanted to escape. That night he read the Dragon Manual, which contained information about all the dragon species the Vikings knew of. In the Night Fury section, all it had was a warning to never engage this dragon.

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The next day, Hiccup sets out to find the dragon. He finds it in the woods, trapped in the net he had shot at it. He takes out a dagger and tells the dragon that he will kill it, but then he finds himself cutting the ropes, freeing it. The dragon leaps up, roars at Hiccup and bounds away, unable to fly due to it's injuries. Hiccup can't believe what he's just done.

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Hiccup can't fight or handle weapons as well as the other Vikings. He wants to prove himself, especially since he is the chief's son, but all the other Vikings shun him for being weak. In the chaos of a battle with the dragons, Hiccup manages to shoot down a Night Fury, the most legendary of all dragons, with one of his inventions. When he tells the others they don't believe him.