Toothcup

Toothcup is the friend ship 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. 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.

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.

Riders of Berk
Before Hiccup met Toothless he had lost every single Thawfest, but now that their peace with their dragons has got Berk to add new dragon-rider challenges to it he left 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 they 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 Hook Fang as his rival. 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
Even though 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 even done and even if he had failed to shoot Toothless that night fate still would have brought the two together. Before they imagine of what their current timeline would have been like if it did happen that way. After the "altered timeline" has Stoick demanded Hiccup to finally made 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 Toothless trap 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, he 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.

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, while in AUs where Hiccup is raised by dragon Toothless is commonly featured as his brother.

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 fandom, like Mericcup, Hijack, Hiccelsa and even Hiccstrid. Whenever fans feature the Light Fury as the dragon of the person they ship Hiccup with.

Fandom
FAN FICTION