Hiccup Horrendous Haddock III/Relationships

Hiccup and the others (Rapunzel, Jack, and Merida)

This focuses on the relationships with the character Hiccup.

Big Four

Friends

Toothless

Hiccup and Toothless

Toothless is Hiccup's first friend and closest companion. Both depend upon one another to a great degree. Toothless is unable to fly without Hiccup, and Hiccup's lack of strength and traditional viking skills, along with his prosthetic leg, are compensated for by Toothless' strength, speed, and raw power. The two of them have become extremely close, and their bond of friendship has survived many harsh trials. Both Toothless and Hiccup have made serious mistakes while dealing with each other. In the first film, Toothless has grown into his loyalty to Hiccup as he and the boy became more and more familiar with each other. Hiccup, later allowed Toothless to fly again, and in doing so he would give the dragon back the thing he held most dear. As the movie progress, Toothless was willing to risk his own life to save his own friend, protecting Hiccup from Hookfang and even go as far as diving his entire body into the exploding Red Death in order to save him. In the second movie, the five-year gap of Hiccup and Toothless' bond grows stronger as the inseparable pair chart unknown lands together. But in later events of the movie, Toothless, under the control of Drago and the evil alpha, kills Stoick and regains his senses unknowing to what has happened. Hiccup shoves Toothless away out of anger and sadness but returns to Berk for him knowing that Drago was the one who committed murder, teaching Hiccup about forgiveness. In the climate of third film, Hiccup and Toothless make the hard choice of parting ways, as Toothless is drawn close his wild mate and Hiccup knew that dragons would never be safe as long as they are in the world of man.

In the fanfiction, authors still keep Hiccup and Toothless' unbreakable bond they share in the film and TV series, as it is an essential part of both of their characters.

Jack Frost

Hiccup and Jack

Being the only two males in the group, Hiccup and Jack are usually portrayed to be close companions, almost like brothers. Since the vikings believed in all manner of supernatural beings - such as gods (the Aesir and Vanir), giants (Jötnar), elves, trolls, and dwarves - fans believe it is very likely that Hiccup would have been able to see Jack. It helps that official materials do describe Jack as an 'ice elf,' and in Norse myth there is a figure said to be the son of the wind god who has a similar name to Jack (Jökul and Frosti were either sons of Kári, or were different names for the same son). It is also said that on Hiccup's native island of Berk it "snows nine months of the year and hails the other three". Though this could be a bit of an exaggeration, it is a fact that the island has some cold weather patterns, which could be a result of frequent visits from Jack. Struggling to feel seen and accepted by his own people, Hiccup would understand by heart the pain Jack goes through, living 300 years completely alone.

As of the fifth Guardians of Childhood book, Jack's staff, Twinetender (or shortened 'Twiner') has been confirmed to come from a tree called the Warrior's Willow, which is located on a Viking burial ground. The staff is stated to contain the soul of a fallen warrior. This gives Jack another potential connection to Hiccup and his culture, beyond the Jökul myth.

In the fandom, the two share a parring "Hijack" which is among the popular ships, aside Jelsa, Jackunzel, Hiccstrid and Mericcup.

Merida DunBroch

Hiccup and Merida

Hiccup is well-rounded and mellow, Merida is passionate and aggressive, but as they say–opposites attract. Because of their very different yet similar personalities, Merida could be quite reminiscent of Astrid's relationship with Hiccup (where she punches him as a sign of affection). In the film Brave, hints a feud between her kingdom of DunBroch and the Vikings ("invaders from the sea"), leading fans to believe that it could be possible for Hiccup and Merida to meet and possibly become friends or star-crossed lovers. They both have some troubles in the parent department (Merida with her mother and Hiccup with his father) and are misunderstood in their society (Hiccup is expected to be more manly, Merida is expected to be more lady-like), so they can relate to each other on that level. There have been many times when fans replaced Astrid with Merida, even to the point of making Merida mother of Hiccup's children. Even without romance, Hiccup and Merida are shown to have a close bond.

Rapunzel Corona

Hiccup and Rapunzel

Within the big four, Rapunzel and Hiccup seem to have the most similar personalities. While Jack and Merida tend to be more fiery and ferocious, Rapunzel and Hiccup are calmer and rely more on their intelligence than a special ability or power. In which meaning that they would be quite comfortable and conversational with one another, sharing the same interest (such as reading and painting) that Jack or Merida wouldn't be fond of. They both appear to be animal lovers (fans have pointed out the parallels between Hiccup's interactions with Toothless and Rapunzel's interactions with Maximus) and generally kind-hearted individuals. Another thing the two have in common it that they born as the only child in their families and ended up getting separated from their mothers when they were just babies, but were able to be reunited with them years later. They also had trouble with their overprotective fathers, but were later able to sort things out with them.

In the Harry Potter AUs, Hiccup and Rapunzel are both interchangeable between Hufflepuff and Ravenclaw, because they both have characteristics that could suit both. They have a pairing called Hiccunzel which may not be the most popular ship, but is still well known in the RotBTD crossover.

Enemies

Red Death

Hiccup and Toothless VS. the Red Death

There is no specific type of relationship that Hiccup and the Red Death have, but that this monstrous dragon is responsible for the 300 year war of Vikings and dragons, ordering the dragons to attack Berk and deliver food to their queen. Hiccup only sees a gigantic "alpha" dragon, who uses the wild ones to survive.

After the final battle, Hiccup loses his left leg, but in the process begins an alliance between Berk and the Dragons.

Pitch Black

Hiccup views Pitch as one of the biggest threats he has ever fought, someone who spread fear and darkness into the hearts of children. Hiccup, most likely keeps his guard up when batting the Nightmare King. In Pitch's advantage, he uses the scrawny Viking's weaknesses and self-doubts to exploit him, mainly by the sight of Toothless and his friends hurt. Though clearly underestimated, Hiccup's strong will and never-give-up attitude is all for a match for Pitch's mental attacks.

Mor'du

Being a demonic bear that once was a prince, Hiccup clearly knows that this is an animal who is not to be taken lightly. Though Mor'du pays little attention to him, however with Toothless is a completely different story. Two powerful creatures that would lead to violent brawls when the dragon's protective instincts over Hiccup kicks in. Alone in battle with Mor'du, who solemnly relies on brute strength and force, Hiccup would be able to defeat him with his brains and resourcefulness.

Mother Gothel

As the cold and heartless woman that Gothel tends to be, Hiccup holds a slight anger towards her due to the fact that she kidnaps and imprisons Rapunzel her entire life, only to use the magic contained within her to stay young. Gothel would often taunt Hiccup for his weak stature and uselessness, but, knowing the vast intellect that he holds and also recognizing true danger of Toothless, would be wary of what a dragon and rider are capable of.

Expanded Universe

Friends and Allies

Queen Elsa

Hiccup and Elsa

Having known about (and possibly fearing) Vikings, Elsa would be very surprised when she meets Hiccup. Socially awkward, smart, and very sweet, the two would get along fairly well. Because he is the son of the Chief, if Hiccup forges a friendship with Elsa, it would give Berk a new trading partner and ally.

Their friendship goes on deeper to a stronger sense of trust and kindness for one another; out of all people, Hiccup can fully understand the pain and fear Elsa goes through from carrying her powers and Elsa can compare Hiccup's said loneliness to hers.

Beyond friendship, the two have a pairing, called Hiccelsa, that is fairly popular with the other well-known pairings. Elsa is most often paired with Hiccup's older self, often meeting either through one of Hiccup's travels with Toothless.

Princess Anna

Hiccup and Anna

Anna is outgoing and positive. Hiccup is cynical and introverted. It would be found difficult to describe what their relationship would be. Hiccup and Anna are both rather clumsy and socially awkward, but at the same time, friendly and charming. They are also both very loyal and determined characters who will stick by a friend or sibling’s side even if the whole world is against them. Anna's optimism may allow her to connect to him through Toothless, immediately wanting to ride him and experience flight. In different scenes of Frozen, Nordic runes can be seen carved in stone in different locations, implying cultural similarities between Berk and Arendelle.

A pairing Hiccanna exists in the fandom though vaguely popular.

Hiro Hamada

Hiccup and Hiro

Although not much is known about Hiro, fans already compare him to Hiccup, as they are both very intelligent, the same age, and both have very unusual "companions". (Baymax for Hiro; Toothless for Hiccup). Fans also say that they would be great friends in the crossover.

Hiccup can also resemble Hiro's older brother Tadashi, who wants to help many people in the form of Baymax, and Hiccup who desires Dragons and Vikings to live together in harmony. Because of Hiccup's empathy, he truly understands the pain Hiro has gone through and would act as an older-brother figure to him, as Hiccup will learn to be responsible for someone much younger than him, protect Hiro, and lead him to the right path such as Tadashi did.

In Hiccup's experience, he has grown to become a mature young man who was brave, fearless, and stood up for what he believed in, Hiccup has become a capable leader to the Dragon Riders and of Berk itself (passing the role of Chieftain), but to become responsible to this young robotics prodigy can be somewhat of a challenge, knowing of Hiro's recklessness and antics can be very unsettling, but would greatly shift Hiccup's character (due to the lack of young child characters in his series). This also evidence the strong similarities between him and Tadashi (if the two were ever to meet, and if so the two would instantly bond), knowing that Tadashi loves Hiro, the strong bond they share, and would be by their side no matter what, but learning Tadashi's death and the empty void in Hiro's heart, this will give Hiccup the opportunity to become that responsible older brother that he needs to be.

Mavis Dracula

Being the outgoing person that she is, Mavis would probably be the first to approach Hiccup, and might be very interested in his dragon. Both Hiccup and Mavis appear to live in fantasy worlds filled with amazing creatures, and since Mavis doesn't get out of the hotel very often, she would probably love flying around with Hiccup and Toothless. The two would probably get along well, also relating on a personal level since they both had trouble relating to their fathers in their movies. Beyond friendship, Mavis and Hiccup also have a ship called Mavcup, which has several fans.

The Once-ler

Both characters are shown to be creative and skilled inventors, so it is likely that they may share stories of that together. While Hiccup is more perceptive and accepting, the Once-ler tends to be short-sighted and stubborn, and this could cause disagreements among the two. However, both characters have a strong sense of optimism and determination, so it is likely that they would get along fairly well.

Mary Katherine

Off all the characters in the fandom, Hiccup and MK tend to be the most introverted. It may take a bit of a push from their friends to get them to interact, but once they do start talking, most fans agree that they would form a strong bond. Both of them had trouble relating to their fathers, and both of them lose one of their parents at one point in their films. While they may not hang out together all the time, most fans believe that they would be good friends and could relate to each other on a very personal level.

In The Knights of the Epic Brave Dragons, MK is portrayed as Hiccup and Merida's daughter, sometimes being depicted as a "Daddy's girl." In other universes, the two may simply be shown as friends or may even be paired up romantically.

Moana Waialiki

Both Hiccup and Moana are the children of chiefs, heir to their tribes and dream about the world beyond their island homes. Both of them were hesitant to accept their roles as leaders at first, wanting instead to explore the world. However, both soon learn to accept their roles and they mature. They would most likely get along well. Hiccup's sarcastic and serious nature combined with Moana's whimsical brashness would also make for an interesting dynamic. Beyond friendship, Moana and Hiccup also have a ship called Moaniccup, which has several fans.

How to Train Your Dragon

Family

Stoick the Vast

http://www.pinterest.com/pin/360076932680631500/

Hiccup's father is the chief of the village, making Hiccup himself the next in line to become Chief. However, the two seem to be complete opposites of each other: whereas Stoick is large, strong, brawny, and the best Dragon Fighter in the village, Hiccup is lanky, weak, brainy, and perhaps (initially, at least) the worst Dragon Fighter on the island. Their relationship is strained because of these differences, as Hiccup wants to make his dad proud by conforming to Viking norms and attempting to slay Dragons but ends up making things worse most of the time.

Though confused as to what to do about Hiccup's peculiarities as a Viking, Stoick is very protective of his son; he is at first reluctant to send Hiccup to Dragon Training for fear that he will be killed. Moreover, during a dragon raid, it is shown that Stoick, along with everyone else in the village, prefers that Hiccup stay inside and out of harm's way (though this may be because Hiccup is more of a risk to the village than the dragons are to him). Stoick becomes proud of Hiccup when he hears of Hiccup's success in Dragon Training and is elated to finally have something in common with his son, although his attempt at conversation with his awkward son ended in failure. However, after his son's relationship with Toothless is revealed, their small progress with one another is destroyed. Stoick accuses Hiccup of siding with the Dragons and later no longer considers Hiccup to be his son. Their relationship is later mended when Hiccup comes to the rescue of the older Vikings during their confrontation with the Red Death with the help of his classmates and the Dragons used in training, showing his dad his otherwise unseen bravery and leadership. This causes Stoick to apologize for his prejudice against dragons and say that he is proud to call Hiccup his son. Stoick shows how deeply he cares for Hiccup when he believes that Hiccup is dead and mourns, apologizing for not having listened to him before. He shows great happiness when he learns that Hiccup is still alive thanks to Toothless' efforts. Later, Stoick and the village welcome Hiccup as a hero and Stoick finally accepts his son for who he is.

In the TV series, Hiccup is given the responsibility over the dragons. However, partly due to Stoick's emotionally inarticulate nature and moments of unintentional insensitivity, his father's approval and acceptance still proves to be a major source of insecurity in Hiccup's life, and he is shown to go to great lengths to confirm that his father really is proud of him. In Portrait of Hiccup as a Buff, Young Man, after being painted stronger than he is, Hiccup sets out on a treasure hunt that Stoick failed to prove himself. Stoick apologized at the end for making his son feel he had to do something big to be accepted. A more accurate picture was placed in the Great Hall to replace the other one. In Thawfest, Hiccup was determined to finally beat Snotlout. When he decided to throw the race, he apologized to his father, to himself, in his choice. Though Stoick was still proud of Hiccup in how well he'd done.

The two still often have a hard time communicating with each other. In How to Pick Your Dragon, Stoick seems to ignore Hiccup's teaching about how Dragons need trust. Gobber told Hiccup that "it's a father's job to listen to his son, without letting on that he's heard a word".

Stoick is still very protective of his son. After Hiccup and Toothless were kidnapped by the Outcasts, he banned flying Dragons to try to keep him safe. While Hiccup respected his father, he felt he had to go behind his back in case Alvin attacked. The two later reconciled. In Frozen, Hiccup was very concerned about Stoick being paralyzed by the Speed Stingers.

Hiccup is also shown to care for his father. Hiccup was very determined to rescue Stoick from Dagur's clutches when Stoick was taken hostage as a trade for Toothless in Cast Out Part I and Cast Out Part II. Hiccup was even willing to join forces with Berk's enemy, Alvin The Treacherous, just to save his father.

In the second film, their relationship is once again strained. This time Stoick is pressuring him to become Chief, but, as he is not ready for such responsibility, Hiccup runs away from Berk. But for all the problems he and his father had, he still loved his father and was deeply saddened with his sudden death and decides to up hold his father's legacy. In the third film, Hiccup looks back on a moment where Stoick had told him a story of a hidden dragon world and that he believes that he'll be the one of find it. His father's story, and the Grimmel's pride threatening all of Berk's dragons, is what gotten Hiccup to make the decision for the Hooligan tribe to leave Berk so they could find a new home, that is close to the hidden world. When Stoick had told young Hiccup the story, he had mentioned about sealing it, with all of the world's dragons, in order to keep many lives safe, Hiccup knew that while the choice would be hard for all of them, separating humans and dragons from each other would be the only way to keep all of the world's dragons from people like Drago, Grimmel and the Warlords; safe until it was safe for them to return.

Valka

http://rebloggy.com/post/my-art-httyd-hiccup-httyd2-valka-httyd2-countdown/81581423701

Valka loves her son very much and she teaches him more about dragons (including Toothless's hidden spikes and how old Toothless is), despite her being distrusting of humans. She even shows him her secret dragon hideout. Valka also takes him to "feeding time" and they both go flying for a while. Then seems fascinated by Hiccup's flight suit and even hugs him. After Stoick is killed, Hiccup, blinded by grief, tells Toothless to leave and Valka explains that they both know that Toothless didn't do it on purpose, as she states that good dragons controlled by bad people do bad things. When Hiccup and Toothless are encased in the ice by the Drago's Bewilderbeast, she breaks down at the fear she has lost her son as well. After defeating the Alpha, Valka proudly watches Hiccup being anointed as the new Chief.

Astrid Hofferson

http://www.pinterest.com/pin/476396466805075737/

In How to Train Your Dragon, Astrid is featured as Hiccup's friend, second-in-command in the Dragon Academy, and somewhat-girlfriend. This pairing is known as Hiccstrid. At first she held in the same low opinion that everyone else did, however her mind was changed when Hiccup took her flying on Toothless, and his fierce determination to protect the dragon had impressed her. She was devastated when she thought that Hiccup had died fighting the Red Death, only to be overjoyed when he was found alive.

In Gift of the Night Fury, ​they are shown to be closer than friends, with Astrid having no trouble expressing her affections However, in the television series DreamWorks Dragons: Riders of Berk, their relationship is shown to be more awkward, as well as beginning to develop from more than friends to a relationship, as of Season 4. At the end of the "Blindsided" episode, the two finally share a kiss, initiating their now romantic relationship. Afterwards, the two lean affectionately against each other and watch the rest of the sunset together. While at the end of "Sandbusted", the two exchange betrothal gifts, Hiccup's gift to Astrid was once Stoick's gift to Valka before he passed it down to his son, and despite Astrid unable to find anything for Hiccup, he tells her that she is his "greatest gift in the world" and just being here with her is the only gift he needs.

In the second movie, the two are not only an official couple but they are betrothed. This is shown during the Dragon Race at the beginning when Stoick proudly yells "That's my future daughter in law!" after Astrid grabbed the black sheep from the twins. The sequel also shows that Astrid is often and still is his second-in-command, possibly from the fact that they do still develop a friendship over Toothless and both hail from Berk. By the time of third movie, Hiccup and Astrid's relationship is a major subplot in the final installment. As Toothless begins to pull away, Hiccup realizes that he still has Astrid to lean on. While it seems Astrid is reluctant to marry in the beginning, mainly because of the embarrassing way Gobber brings the subject up in front of everyone but also because of her priorities, she quickly realizes how important it is for her to be there for Hiccup and stand by his side. By the end of the movie, Astrid happily weds Hiccup, officially becoming his wife and the Chieftess of Berk. She later proceeds to build a family with him, giving birth to two kids, first an older daughter and then a younger son. Both children seem to share striking similarities with each parent.

Some fans, however, mostly don't tend to place the two dragon trainers in a romantic relationship, instead favoring relationships like Mericcup and Hiccunzel. This does not mean that the two are not close or confidants, it just means that their relationship does not develop past close friends when part of the RotBTD universe.

Zephyr and Nuffink Haddock

http://avannak.tumblr.com/post/183144658768/happy-birthday-dad-sometimes-you-gotta-stop

Sometimes after the dragons left the world of man and descended into the Hidden World, Hiccup became a father to his and Astrid's daughter, Zephyr, as well as to their younger son, Nuffink. When Hiccup and Astrid took their children on a family voyage to the Hidden World, with the siblings doing their part to on their ship, Hiccup introduced the two to Toothless and taught them how to form the bond of trust, by holding up their hands and waiting for the dragon to come to them. Before taking to the air on both Toothless and Stormfly's backs, with the Light Fury and Night Light hatchlings flying closely to them, so their could see and fell the thrills they had with them in their youths. As the Haddocks were sailing closely to the Hidden World, Hiccup carried Nuffink in his arms and let him push down a wooden leaver, that could have been connected their ship's anchor, before letting his son ride with him on Toothless until he placed Nuffink on Stormfly's back with Astrid and helped Zephyr onto Toothless' back, so she could have a turn of riding the Night Fury with her father.

Both children resemble their parents, as Nuffink looks like a child version of Hiccup, with blond hair and Zephyr has her father's Auburn-Brown hair, and has made a few face expressions that look similar to the ones that Hiccup had made from when he was fifteen. Since Zephyr is Hiccup's first born child, there is a chance that she is the heir to the tribe, as well being the first heir to be born on New Berk. The island that the Hooligan Tribe came across on their journey to the Hidden World, and later chose to stay anew on it.

In Mericcup and Hiccelsa stories and mock-up fanart, fans interpret Zephyr and Nuffink as Hiccup and Merida/Elsa's children, or maybe even as whole new characters so as to resemble their parents.

Allies

Gobber the Belch

http://hyoutas.deviantart.com/art/gobber-and-hiccup-358113939

Gobber was always the mentor and second father-figure to Hiccup. Despite acting like all of his other students are expendable or simply paying little attention to their well-being, Gobber seems to have a soft spot for Hiccup. This is obscured, however, by the methods by which he goes about expressing his fondness of the boy. Though his intentions are good, Gobber often gives out comically bad advice that somehow just makes Hiccup feel worse. Most importantly, however, Gobber acts as the bridge of communication between Stoick and Hiccup, since the two seem to be unable to listen to one another otherwise. In fact, Gobber is the one who convinced Stoick to allow Hiccup to enroll in the Dragon Training classes, reminding the latter that he could not always hope to protect Hiccup; the best he could do was prepare him. At the end of the film, Gobber is the one who constructs a new prosthetic tail for Toothless and Hiccup's prosthetic leg. The other important role Gobber filled was training Hiccup in leather-working and as a blacksmith, which gave the imaginative teen an outlet for his mind along with practical design and fabrication skills. If an invention of Hiccup's fails, it's only because inexperience affected the design, never because of faulty parts, or that the parts were poorly crafted. Hiccup's innovation, improvement and engineering of his society's technology for his creations is often nothing short of sheer genius.

Snotlout Jorgenson

Although he would often taunt Hiccup over his lack of skill, he never seemed to hold the same level of dislike for him that he did in the books. When Hiccup starts doing well in Dragon Training, Snotlout quickly joins the ranks of his adoring fans. When Hiccup is shown to have survived his encounter with the Red Death, Snotlout actually sheds a tear in relief. In the series, Snotlout seems to retain the same low opinion that he had of Hiccup from the very beginning (having been proven to be a sign of envy of Hiccup's accomplishments), but is willing to ask for Hiccup for help when things become too bad him to handle. In the show, it is implied that their character dynamic mimics that of Stoick the Vast and Alvin the Treacherous at their age.

Ruffnut Thorston

Not a lot of screen time is shown between the twins and Hiccup. Most of the time, they follow Hiccup's commands, although not always done in the right way. On occasion, they disobey him or misinterpret his orders. Despite Hiccup doubting their abilities most of the time, he acknowledges their abilities to work together if they want to. He gains respect for the twins when they figure out the idea to "fight fire with fire" in Zippleback Down and Tuffnut's ability to train Torch. Although finding them annoying from time-to-time, Hiccup is shown to care for them as he and the other Viking Teens attempt to find them after their disappearance in View To A Skrill Part II and was relieved to find out that Ruff and Tuff were both okay. He also acknowledges their decision to follow Alvin's ship to spy on him. They also care about Hiccup, (even though it's hard to tell), like when they, along with the other riders, were very happy to see that he was alive after the battle with the Red Death and when he fell down a hole, (then came out okay later), in Portrait of Hiccup as a Buff Young Man.

Tuffnut Thorston

At the beginning of the film, Tuffnut was fairly antagonistic towards Hiccup, with the frequent jibe towards his lack of ability to fight or kill dragons, acting as a crony for Snotlout. After Hiccup shows the teens how to train dragons, Tuffnut adopts the idea enthusiastically and trains a Zippleback that he shares with his sister. Tuffnut doesn't often listen to Hiccup, especially when he's teaching in the Dragon Training Academy.

Fishlegs Ingerman

In the original novels, Fishlegs and Hiccup were close friends. In the film, Fishlegs is the only one who neither picked on him, made fun of him or really interact with him on an level. When Hiccup began to suceed in dragon training, he joined the other teens in his admiration of him. Later, Fishlegs learns how to fly on a dragon from Hiccup and ends up flying and owning the Gronckle used in Dragon Training, which he later names Meatlug. His analysis of dragons becomes invaluable for the rest of the Vikings when he identifies the characteristics and weaknesses of the Red Death. In the series, Hiccup and Fishlegs has been shown to have grown closer as friends, being able to match each other in an intellectual level and even acts a third-in-command (second to Astrid), helping re-write the book of dragons for the sake of taming dragons rather than killing them.

Eret

Hiccup and Eret were initially in conflict as Eret attempted to trap dragons for Drago as opposed to Hiccup's respect for them. However, after Eret saw that he was wrong about dragons, he helped the dragon riders return to Berk to face Drago, with Hiccup suggesting that Eret take on Stoick's old dragon Skullcrusher following Stoick's death so that Skullcrusher will still have a trainer, recognizing that Eret can be trusted.

Enemies

Drago Bludvist

Hiccup vs. Drago

After hearing about him from Astrid, Drago seems to acknowledge Hiccup as a rival of sorts, realizing that another dragon-tamer could endanger his monopoly over the dragons. A parallel of sorts to Hiccup, given his own mastery over legions of dragons. Drago is a stark contrast to him as well, using abuse and force to dominate the will of his dragons as opposed to befriending them. When the two finally face off, Drago, identifying Hiccup upon seeing him ride his Night Fury, Toothless, seems amused that his reputed nemesis was little more than a boy, seemingly dismissing the threat that Hiccup posed. While Hiccup still believed that Drago could be reasoned with, he proves otherwise, stating that strength of will was true power and the only way to control dragons -- an ideal he demonstrates by commanding his grey Bewilderbeast to take control of Toothless, and using him to kill Hiccup. Though this fails due to Stoick's intervention, it succeeds in shaking Hiccup's resolve. Drago then takes Toothless as his mount to further demoralize Hiccup. During Drago's invasion of Berk, Hiccup continues to surprise him when he and his companions show up on the backs of baby dragons, which the Bewilderbeast could not control, then again when Hiccup's bond with Toothless frees him from the Bewilderbeast's command. The tables are turned on the infuriated Drago when Hiccup's ingenuity and Toothless' own willpower rise up against the great and terrible grey Bewilderbeast, shaming both tyrants and releasing the dragons from their control for good.

Grimmel the Grisly

Being the best friend of his ultimate prize, Grimmel knows that Hiccup will be an obstacle in his hunt and threatens to destroy everything the young chieftain loves if he does not give Toothless up.

Grimmel is revealed to be a dark version of Hiccup, a version who kills the Night Fury he captured instead of saving and befriending it.

Other

Alvin the Treacherous

Alvin and Hiccup

In the books, Hiccup and Alvin are arch enemies, and they keep that feeling of animosity in the TV series. Alvin clearly has some sort of history with Hiccup's father, and recognizes Hiccup as "Stoick's little embarrassment" and "Stoick's little runt". Hiccup at first outsmarts Alvin into taking him to dragon island. It is there that Alvin realizes that Hiccup is a master dragon trainer. Alvin then begins to try to train dragons of his own, but he fully realizes that to do so he will need Hiccup. He abducts him several times throughout the franchise. Hiccup is usually sarcastic around Alvin which annoys the Outcast chief considerably, showing the amount of contempt he has for the bloodthirsty chief. Hiccup and Alvin both clearly underestimate each other. Hiccup was completely fooled by Alvin's plot to lure him to the Isle of Night, and Alvin has many times watched helplessly as the "90-pound boy repeatedly defeats an army of blood-thirsty savages." Alvin is Hiccup's main enemy in the television series, and he is one of the few characters that Hiccup has openly ordered Toothless to finish off. The animosity between the two of them has grown and grown as Hiccup has escaped Alvin and Alvin has nearly destroyed things that Hiccup cares deeply about. Alvin has notably targeted Astrid, and this has served to fuel the fire of the rivalry. Then Alvin discovered he could use Hiccup's love for Toothless to get at him, and this seemed to be the final straw. When Hiccup finally escaped, he and Toothless made a diving attack at Alvin and would have most likely killed him if they had not been downed by bolas. It is rare for Hiccup to be so determined to kill an enemy, but Alvin has given him good reasons to reach such decisions. Alvin has now trained a dragon, so it is highly likely that he and Hiccup will become even more embittered towards each other.

The Screaming Death

Hiccup and the Screaming Death's relationship started with much turbulence. The Screaming Death and its siblings spent their first few days of life rupturing the foundations of Berk and terrorizing it's residence. Hiccup was able to outsmart it and leave it injured, escaping to fight another day. Eventually their paths cross again, Hiccup, the other dragon riders and the dragons of the islands that it destroyed driving it off before it tries to destroy anything else.

Hiccup eventually realized from Alvin that the Screaming Death was actually just looking for its mother on Outcast Island. During a harrowing battle against Dagur, the Berserkers and the Outcasts, Fishlegs and Meatlug used Dragon Root to lure the Screaming Death and its siblings to Outcast Islands to help even the odds, while Snotlout and Hookfang freed the caged mother. The Screaming Death, grateful, roars at Hiccup and Toothless for a bit and leaves with its family. Whether or not they will cross paths again is unknown. Later in Race to the edge season 2 their paths cross again but it seems that the Screaming death doesn't remember Hiccup and his good deeds, until it's mother stop her hatching from attacking the one that brought them together.

Dagur the Deranged

http://inhonoredglory.tumblr.com/post/55125283456/thejotaku-commission-for-sangrette-of-hiccup

Hiccup and Dagur have known each other for a long time, usually meeting with their tribes' treaty signing. Dagur often acts like a pesky older brother, using Hiccup as a knife throwing target or trying to drown him. Hiccup describes him as a "lunatic kid" and was not happy to learn he was the new Beserker chief. Dagur confronted Hiccup about the Red Death and trained dragon rumors he heard about, only for Hiccup to deny them. The dragon trainers staged a dragon attack to save Barf and Belch, and the Beserkers retreated. Hiccup later met up with Dagur again on Dragon Island, happy to see Hiccup alive after the "attack" and kept going on about how he faced a Night Fury. Dagur then decides the two of them will hunt down the dragon together. He even starts calling Hiccup "brother," which he finds awkward. Dagur points out he and Hiccup are a lot alike: both are born leaders, sons of chiefs, and have fathers that had to be elimitated; the last one Hiccup quickly disagrees with. When Dagur learns that the truth about Berk's dragons, he feels betrayed and attacks Hiccup and Toothless. Hiccup beats Dagur, and he and he others head back to Berk, as they need to be ready when Dagur returns. After being defeated and telling the Beserker armada, Dagur tells them no one is to hurt Hiccup, except him, after he gets his dragon.

After losing the symbol of his people, the Skrill, to Hiccup and Toothless, Dagur's pride was badly hurt, making him even more determined to capture the rider and his dragon. Dagur also tried to make Hiccup choose to give Toothless up for the sake of his loved ones, such as the Dragon Riders and Stoick.

After being imprisoned, Dagur focused on getting revenge on Hiccup more than ever. He also kept calling Hiccup "brother," though more of in a mocking tone.

After his resolve, Dagur tried to prove himself to Hiccup he had changed. He protected Hiccup from a group of Dragon Hunters, as well as come up with an antidote for dragon root when Toothless had been hit by their arrows. When they were captured, Dagur saved Hiccup from being branded and released him, with Toothless' help. Between the two events, Dagur looked hurt when Hiccup shout that he hated the Berserker when he left him behind to get Toothless.

Dagur went to Hiccup again seeking help to become a dragon rider so he could search for his sister. While Hiccup was reluctant, he agreed, much to Dagur's joy. He continued to show gratefulness and admitted to his mistakes during training. When Dagur learned that Heather was with the Dragon Riders, he was more disappointed in Hiccup for keeping the secret instead of getting mad. When Dagur saw the plans for the Riders attack, he tried to warn Hiccup it was a trap. Dagur later rode out to prove he was right, and to protect his sister, possibly costing him his life. Hiccup was left feeling guilt-ridden for not believing him.

When Dagur returned, Hiccup had doubts about trusting him, but Dagur eventually proved himself to be a worthy ally when needed most.

Light Fury

Due to what she had been through, before meeting Hiccup, she initially mistrusts him for being human, and despite Hiccup not presenting himself as a fret to her or other dragons, it didn't stop the Light Fury from tossing him into the ocean in mid-air. Sometime after the Light Fury was recaptured and later drugged by Grimmel, so he could ride the white scaled dragon against her will, while battling Hiccup and Toothless in the air, Hiccup is able to find an opening that allowed him to free the Light Fury from the dragon hunter's control. While his actions allowed the Light Fury to regain her freewill by breaking Grimmel's hold on the wild dragon, Toothless was falling in mid-air which led to Hiccup telling her to save him. Understanding of what he said to her and feeling him letting go of his grip on her, so the Light Fury could save the dragon they both care about; she went to save Hiccup as her next priority.

Hiccup's actions in the battle that saved the two Furies and many other dragons from the wrath of both Grimmel and the Warlords, helped the Light Fury to see that not all humans are them and that there are humans that are kind to dragons. Moments before all the dragons left the world of man and descend to the Hidden World, Hiccup tells the now friendlier Light Fury that Toothless is all hers. Years later, a much older Hiccup journeys back to the Hidden World, with Astrid and their children so they could met their dragons friends, the human trusting Light Fury, along with her and Toothless's three hybrid hatchlings and fly beside both her mate, Stormfly and the Haddock family.

In some fan rewritten and vice versa work of the How to Train Your Dragon franchise, the Light Fury takes Toothless's place as the dragon that changed both Hiccup and the rest of Berk's lives, for the better. There have also been fans that have the Light Fury giving Hiccup a much earlier on chance to gain her trust.