In the village of Berk, fighting dragons is a way of life. Stoick's son, Hiccup, is not big and strong like the other Vikings. Instead, he is weak and gangly, has a weird sense of humor, and always thinks things through instead of charging blindly. Trying to prove himself to his father and the others, Hiccup decides to kill the extremely rare and never captured before Night Fury. He manages to shoot one down during the raid, but is unable to convince the other Vikings of that. Attempting to get proof, he sneaks off and manages to find the dragon he shot down, which is indeed a Night Fury. But, Hiccup can't bring himself to kill the helpless creature and frees the Night Fury instead. After a tense standoff, the dragon flees.
Following this, Hiccup is enrolled in dragon fighting classes, which are taught by Gobber the Belch (Craig Ferguson), Hiccup's armory teacher. The class includes five other teenage Vikings: Astrid (America Ferrera) (who Hiccup has a crush on), Snotlout (Hiccup's cousin) (Jonah Hill), Fishlegs (Christopher Mintz-Plasse), and twins Ruffnut and Tuffnut (Kristen Wiig and T. J. Miller). Elsewhere, Stoick gathers and leaves with another search party that is attempting to find the Dragon's Nest, the apparent stronghold of the dragon race.
As he learns more about dragons, Hiccup again finds the Night Fury trapped in a small canyon. Hiccup soon sees that one half of the dragon's tail wings was ripped off during his crash landing and has left him unable to fly. Trying to make things right, Hiccup slowly gains the dragon's trust and names him Toothless (his teeth retract back into his gums when he's not eating, so he appears "toothless"). As the two continue to learn about each other, Hiccup constructs an artificial tail and saddle for Toothless, enabling him to fly again, but only with Hiccup's aid.
Meanwhile, back in Hiccup's dragon fighting classes, Hiccup begins to have great success. He appears to have an almost supernatural control over the practice dragons that the students have to fight. The secret that the other students don't know is that Hiccup is using facts he gleaned from Toothless to control the other dragons. Or another where he finds "cat nip" but for dragons to fight a gronckle. On one flight with the Night Fury, Toothless gets in a small quarrel with some smaller dragons called Terrible Terrors, but easily incapacitates them by spitting fire into their mouths. Meanwhile, Astrid begins to get jealous of Hiccup's success and suspicious of his escapades into the forest to see Toothless.
After a hard journey, Stoick's search party returns, suffering light damage and having no luck finding the Nest. He discovers his son's natural talent with the dragons and congratulates him by giving him a helmet made from his mother's breastplate, like his own. Hiccup eventually becomes the top student in his class using everything he has learned about dragons from observing Toothless and gets the chance to slay a Monstrous Nightmare, one of the most dangerous dragons. However, Hiccup doesn't want to kill any dragons, so he plans to leave Berk with Toothless. However, Astrid follows him to their hideout and discovers Hiccup's friendship with the dragon. She tries to run back to the village, but Toothless kidnaps her and Hiccup asks for a chance to explain. They take her for a ride and Astrid begins to see how amazing dragons really are. During their flight, they get caught in a herd of dragons carrying food and follow them to their nest.
There, they discover that the dragons steal food to feed a much larger and more threatening dragon that eats them if they do not provide enough food. After they leave, Astrid wants to inform the village of the nest's location, but Hiccup decides against it in order to protect Toothless from the other vikings. Astrid agrees to keep quiet and then punches Hiccup on the shoulder for kidnapping her but then kisses him on the cheek for the ride.
The next day, during Hiccup's battle with the Nightmare, he throws down his weapons, saying he's not one of them and tries to show everyone that dragons are not as bad as they seem. Stoick shouts to stop the battle before Hiccup can continue, and the Nightmare attacks in reaction to Stoick's rage. Meanwhile, Toothless senses that Hiccup is in danger and races off to Berk. Just before the Nightmare can finish Hiccup off, Toothless comes in and defeats the Nightmare.
Hiccup pleads Toothless to flee, but he ignores him, fearing that the other vikings pose a threat to Hiccup. Toothless almost kills Stoick, but Hiccup begs him to stop, and Toothless immediately becomes more docile. In this peaceful state, Toothless is quickly overpowered and captured. Stoick confronts his son angrily at learning about his son's friendship with a dragon. Hiccup accidentally tells him that he has been to the nest, and Stoick decides to use Toothless to lead them there. Hiccup begs him not to hurt Toothless and warns them of the giant dragon that they likely stand no chance against, but Stoick ignores him.
The vikings set sail with Toothless, chained, to finish off the dragons for good. Back at Berk, Astrid comforts Hiccup and asks him what he is going to do. Hiccup decides to use the dragons that the vikings use for dragon fighting practice to fly to the nest. Meanwhile, Astrid has gathered Ruffnut, Tuffnut, Fishlegs and Snotlout to help. Each mount on the dragons and set off after the vikings.
As the other vikings arrive, they prepare for battle, but all the dragons flee the island. Stoick discovers the even bigger dragon, Seadragonus Giganticus Maximus, which sets all of the boats on fire, including the one Toothless is chained up on. Hiccup and the others arrive, and while he goes to free Toothless, the others try to learn of any blind spots or shot limits of the giant dragon.
The boat collapses and Toothless sinks, still chained. Hiccup tries to free him but nearly drowns. Stoick saves his son and jumps back in to save Toothless. Hiccup and Toothless then lead the giant dragon into the air and shoot at its wings. They then dive into the ground and set fire to the dragon's insides. The giant dragon tries to pull up, but the shots fired previously have torn holes in his wings, sending him crashing into the ground and exploding in a thunderous inferno. After crashing in the bigger dragon's tail, Hiccup is knocked out and falls off Toothless and into the fire. Toothless dives in to save him, despite his saddle damaged and artificial tail destroyed.
Stoick searches the rubble for his son and only finds Toothless. At first everyone thinks Hiccup died in the fire but Toothless reveals that he had wrapped Hiccup up in his wings to shield him. Hiccup reawakens in his home and finds Toothless by his bedside. He also finds that his left foot had been lost in the battle with the giant dragon, replaced with a spring loaded prosthetic by Gobber using the boy's designs. With Toothless' help, Hiccup slowly makes his way outside and sees that vikings have invited dragons into the village and are constructing shelters and giant feeding bowls for them. Everyone welcomes Hiccup back as a hero. Astrid then punches Hiccup on the shoulder for scaring her when they thought he was dead but then kisses him. Hiccup is then given new equipment for Toothless built by Gobber. Hiccup and Astrid ride their dragons through the newly reformed Berk as the long war between Vikings and dragons is put to an end.
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