Toothcup

Toothcup is the friendship between Hiccup Horrendous Haddock III and Toothless from the How to Train Your Dragon fandom.

How to Train Your Dragon (film)
Because Hiccup isn't like any of the other Vikings on Berk and just wants to be expected by them, mainly his stubborn father, he believes that killing a dragon will change his life for the better. Once he hears one of the Vikings cry out Night Fury, which is the rarest of all dragons, Hiccup decides to go after the dragon by using one of his inventions to shoot the said dragon out of the sky. Even though Hiccup was able to shoot the Night Fury down in it's dark element, no one believed his clam of shooting the dragon down. So he decides to make his way to the spot that he saw the dragon land and bring back the dragon's heart as proof of his clam. When Hiccup came across the dragon, however, he couldn't bring himself to kill the Night Fury and ends up setting the dragon free. This encounter got Hiccup to realize that he doesn't want to fight dragons after all, Stoick the Vast however wants his son to start his dragon killing training while he leaves to find the dragons' nest.

During Hiccup's first lesson Gobber tells Hiccup that a dragon will always go for the kill, but the dragon he speared didn't and ends up going back to the spot where he last saw the Night Fury. When the dragon had left Hiccup he got himself trapped in a cove that he can't get out of, Hiccup didn't know why that is while he observes the Night Fury from a safe distance. As he notices that the dragon is missing part of his tail fin. During his next dragon killing lesson, after Hiccup had failed to find facts on Night Furies in the Book of Dragons, he tries to ask Gobber questions about them but Gobber didn't know anything about Night Furies either. Since no one else has ever survive their encounter with one and believe that it is best that they keep distance away from that type of dragon. Who many call the unholy offspring of lightning and death itself. Despite being told this Hiccup returned to the cove with a fish for the dragon, to show the wary dragon that he means no harm to him Hiccup throws his knife into the water, but as Hiccup gives the dragon the fish he sees that his mouth toothless until the dragon's teeth retract back out. The night fury then spits out half of the fish he wants to share with Hiccup, to not hurt the dragon's feelings Hiccup takes a bite of it. A few hours later the dragon sees the drawing that the human has done of him before he draws one of Hiccup. Once Hiccup found his way out of the drawing without stepping on the lines of it, he notices that he has approached the dragon before he reaches out his hand to touch him. At first the Night Fury didn't want to be touched until Hiccup looked away and kept his hand out stretched for the dragon to come to him. Later at night fall Hiccup learns from Gobber that a down dragon is a dead dragon, knowing that he is the reason that the Night Fury can't why anymore, Hiccup felt responsible for what he had done and decides to apologies to the dragon by helping him to fly again. By using his blacksmith skills to build the night fury a prosthetic tail fin, to replace the one he lost.

The next morning Hiccup bring the dragon some fish, since he had trouble getting food on his own, before he begins to place the tail fin sail on the dragon's tail he learns that dragons don't like eels. Hiccup had also decided to name his new dragon friend, "Toothless". As Toothless ate the fish Hiccup began to fix the tail fin sail onto the dragon, without his knowledge until Toothless count onto him. Even tough Toothless did get back into the air for a few short seconds, as long as the prosthetic tail fin is opened, Hiccup knew that he still needs to work on it. This is why Hiccup built a saddle to help him work the tail fin for Toothless, and has they worked on it together Hiccup learns that everything his people know about dragons are wrong. Hiccup's time with Toothless has also helped him gain the skills to pass dragon training, without harming any of the ring's dragons, as he becomes top of his class and finally gets excepted by his tribe. When Hiccup was told that he'll be the one to kill the Monstrous Nightmare in front of the whole village, with his father being one of the one, Hiccup knew that he couldn't do it and decides to runaway with Toothless. Before they could leave, however, Astrid Hofferson discovers Hiccup's secret friend, who helps Hiccup change Astrid's mind about him as Toothless takes the two out for a flight. During this flight Toothless ends up taking Hiccup and Astrid to the very island that Berk has been searching for since their war with the dragons began. Astrid wanted to inform Stoick of this but Hiccup asks her to keep their discovery a secret, as he was worried of what his father would do to Toothless once he finds out about him.

Riders of Berk
Thawfest

Before Hiccup met Toothless he had lost every single Thawfest, but now that their peace with the dragons has got Berk to add new dragon-rider challenges to the games he felt that he finally has a chance to win. During the Viking related challenges Toothless painfully watches Hiccup loss, until they get to the newly added dragon challenges as the two win each challenge together. As they tie with Snotlout, who's family have won every Thawfest. Like Hiccup is with Snotlout throughout Thawfest, Toothless begins to view Hookfang as his rival. As Hiccup tries to out do Snotlout's smack talk, before the new dragon challenges began, he ends up calling himself and Toothless "Hictooth". To help them win the last challenge Hiccup upgrades Toothless's prosthetic tail fin and saddle to give them an edge. Just as the two were about to win, however, Hiccup realizes that he has been a bully to Snotlout who is now him during Thawfest, Hiccup gets Toothless to throw the race. Since winning isn't everything and Toothless did finally help Hiccup gain a place for him in the games.

Defenders of Berk
Live and Let Fly

Even though both Hiccup and Toothless were able to escape Outcast Island after their kidnapping, Stoick thought it best that they kept the dragons grounded as they prepare for future attacks from their enemy tribe. Hiccup knew that his father's orders wouldn't sit well with Toothless, who loves being in the air as much as Hiccup does.

Race to the Edge
Season 6

When Stoick got gravely hurt in "Darkest Night", Hiccup began to wish that he never shot Toothless out of the sky that night, since all of the bad things that have happened to Berk are because he tamed a dragon. Astrid manged to convince Hiccup that him meeting Toothless is the best thing he has ever done and even if he had failed to shoot Toothless that night fate still would have brought the two together. Before they begin to imagine of what their current timeline would have been like if it did happen that way. In the "altered timeline" Stoick demands Hiccup to finally make his first dragon kill out at the forests and how he can't return until he does so, Hiccup ends in the every cove that he and Toothless became friends in. Like in the original timeline Hiccup had manged to trap Toothless and couldn't bring himself to kill the dragon. A Whispering Death then bursts out of the ground and attacks the two. Hiccup does what he can to help Toothless fight the second dragon, before the Night Fury spirits the human into the open sky, where both Stoick and Gobber see him riding a dragon. The Whispering Death, however, wasn't going to let the two leave and fires at them as the other dragon's flames gravely injured Toothless's tail fin. After the two crashed, where Hiccup gets knocked out after he got hurt by the Whispering Death, Toothless uses his body to shield Hiccup from the rest of the enemy dragon's attacks. Until Stoick and Goober arrive to help Hiccup. Seeing how the Night Fury cares about Hiccup and had protected him from the Whispering Death, Stoick welcomes the dragon into his tribe. Hiccup learns this when he woke up to find Toothless smiling at him before the dragon shows Hiccup his prosthetic tail fin while Hiccup as a prosthetic leg. Their new friendship has Stoick declaring their war with the dragons over. Thinking about that alternate timeline helped Hiccup to realize that Astrid it right about him and Toothless.

How to Train Your Dragon 2
When the two turned twenty, Hiccup and Toothless have been flying across the world as Hiccup maps out the places he and Toothless discover together.

How to Train Your Dragon: Homecoming
The events of the Christmas short takes place before the epilogue of the third film, as it shows that Toothless's family was the one to visit Hiccup's first on New Berk before he takes his family to see Toothless's at the entrance to the Hidden World.

Fanon
Toothcup is one of the most popular friendship ships of the How to Train Your Dragon fandom. There have even been a few rare occasions when fans treat Toothcup as a slash ship, by turning Toothless into a human or a dragon-human hybrid version of himself. Which is similar to how fans feature Hiccup a human-night fury hybrid, turn him into a night fury, or have given him night fury-like abilities or based clothing, for fun. In a few Modern AUs fans have Toothless as Hiccup's pet cat or dog, along with portraying the night fury as a wolf who Hiccup befriends, while in AUs where Hiccup is raised by dragons, or have the two meet one another at a very young age, Toothless is commonly featured as his brother. There have also been fans who compare Hiccup and Toothless to Hiro and Baymax, Lilo and Stitch, and many other human-animal/none-human duos who are similar to both of the two or just one of them.

In the popular  crossover fandom, and its sup-fandoms, Hiccup's friendship with Toothless has fans include the dragon in the crossovers beside his rider. Along with shipping NightLight beside some of Hiccup's crossover ships in the fandoms, like Mericcup, Hijack, Hiccelsa and even Hiccstrid. Whenever fans feature the Light Fury as the dragon of the person they ship Hiccup with, or have Toothless help Hiccup to become close to them. The former Strike class mark, of a Night Fury (which is also the dragon symbol of Berk's Dragon Training Academy), along with the white symbols on both Toothless' first and second red tail fin sail are sometimes seen as one of Hiccup's commonly used personal marks. Fans use some of these Hiccup and Toothless related markings to serve as Hiccup's "heart", whenever they place it beside the heart mark of the person or friendship group they ship him with.

Fandom
FAN FICTION
 * Hiccup/Toothless tag on FanFiction.Net
 * Hiccup/Toothless tag on FanFiction.Net
 * Hiccup/Toothless tag on FanFiction.Net

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WIKIS
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Variations

 * Hijackless refers to the ship between Hiccup, Jack Frost and Toothless
 * Toothlightccup refers to the ship between Hiccup, the Light Fury and Toothless