Toothless

**Toothless** is the name of Hiccup's Dragon in both the book series and film. In the books, Toothless is a young Seadragonus Giganticus Maximus, although it is originally believed he is a Common or Garden Dragon, while he's a larger, black Night Fury in the film adaptation He is the quintessential dragon in the series, and remains unrivaled in intelligence.

And he is the Alpha of the Dragons of Berk and Equestria alongside Nightstar

## Bio

Toothless appears as a Night Fury in the film, the rarest and most intelligent species of Dragon there is. He plays a similar role to his book counterpart.

### Personality

Toothless proves himself to be a very capable fighter, such as when he rushes to Hiccup's aid in his battle with the Monstrous Nightmare, Toothless quickly causes the larger Dragon to back down. Toothless also shows himself superior to most Vikings, as proven against Stoick in a quick skirmish.

Toothless is very intelligent and seems to have a dry sense of humor, similar to Hiccup's, which he may have picked up from Hiccup. He doesn't take kindly to being offended nor anyone offending or endangering his human friend but is usually playful, docile, maybe even a little teasing when not threatened. He also shows a great curiosity, imitating Hiccup's actions and mannerisms when they initially encounter one another like when he was observing Hiccup draw him, he then tries to draw with a tree branch. Toothless' intelligence shows many times throughout the film, being able to understand Hiccup's words and commands as well as agree with some of what he says. It is shown that he has become aware of Hiccup's crush on Astrid, even seeming to briefly tease him about it.

Toothless actually can get display a bit of an attitude. He gives a Terrible Terror an extremely snide look when it is challenging him to a fight. He clearly understands his own strength, and is not always humble about it.

He isn't intimidated by Astrid and walks off with a sort of shoulder shrug and eye roll when she threatens to expose Hiccup's and Toothless's friendship to Stoick. He certainly displays an independent attitude when he takes both Hiccup and Astrid on a roller-coaster ride directly after Hiccup tells Astrid that he is harmless. Toothless does not seem to agree with Hiccup on that point. Toothless also smacks two Outcast guards with his tail as he leaves his cell to look for Hiccup. This attitude is usually hidden under his docile nature, but it comes out in comical ways from time to time.

Hiccup and Toothless share an unrivaled bond of friendship with one another. Hiccup refers to Toothless as his best friend often throughout the franchise, and even Astrid refers to him as that. The two spend almost all of their time together in the events following the movie. In Dragons: Riders of Berk. Toothless sleeps in the house with Hiccup and follows him almost wherever he goes. None of the other Dragons are shown to have quite as much loyalty as Toothless. He is protective, supporting, and caring towards his rider. He's not just an amazing pet; he is Hiccup's closest friend.

#### Physical Appearance

Toothless is much larger than his book counterpart, being much bigger in size than Hiccup. He has jet-black scales covering his whole body, his sides having small light patches in a pattern similar to that of a manta ray. Toothless possesses two sets of wings (one main pair and one smaller pair near the base of his tail). He is missing the left side of his tail-fin, which he lost when Hiccup took Toothless down with his Mangler.

This is later replaced by a mechanical fin that Hiccup constructs himself. Toothless has a rather large scar on his right shoulder/neck which is around a foot in length with a width of about an inch. Toothless's eyes are a bright green. They are located very near the front of his face giving him excellent depth perception and reflexes in flight. He can narrow his pupils to slits when threatened or angry, similar to that of a cat. But when he is docile or happy, his pupils dilate and become more dog-like. Toothless gets his name from his sets of retractable teeth.

Toothless is the only Night Fury seen thus far in the franchise, so his physical appearance is all that can be studied to learn about Night Fury anatomy. He has two extremely large wings that allow him to do a vertical takeoff. Behind that is a set of smaller wings that aid in gliding. At the end of his tail he used to have yet another set of wings that aided in steering and stability, but his left one is now missing.

In *How to Train Your Dragon 2*, The spines on his head and forelegs are slightly longer. He also has three sets of extra plates growing on his lower jaw. He is also revealed to have a set of extended spines running along his back that aid him in making tight turns. Toothless didn't know about them, but they were revealed by Valka. But other than that he is identical to how he looked in the first movie. Toothless is also a lot more playful than he was in the first movie. It is also revealed by Valka that Toothless is the same age as Hiccup. This may be another reason for how well the duo get along.

### *How to Train Your Dragon*

Toothless is considered Hiccup's first and best friend in the films.

Toothless is actually the first character to be seen in the entire franchise. He flies behind the Dreamworks logo and then vanishes into the night sky. Presumably, he lived in the Dragons' Nest along with all the other Dragons that would raid Berk. His first actions are to dive bomb Berk. Though he does not steal food, he does target catapults. He destroys the catapult Stoick is using to fend off Deadly Nadders. His strikes are strategic and lethal, and he seems to be the only kind of Dragon Stoick will become concerned about. Hiccup sees the destruction caused by Toothless and decides to prove himself by doing the impossible: bringing down a Night Fury.

Hiccup shoots Toothless down with his mangler cannon when Toothless dive bombs another one of Berk's catapults. Toothless is caught in the bola and falls shrieking from the sky. He crashes into the woods just past Raven Point. During the crash, Toothless loses his left tail-fin, leaving him forever crippled from natural flight. He lays unconscious in the woods tangled in the cords of the bola until Hiccup discovers him.

Toothless stares deeply into Hiccup as the boy prepares to kill him. The boy is shocked to see how frightened the mighty creature is. Hiccup is unable to kill Toothless, so instead he begins to cut the ropes.

As soon as he is free, Toothless whips around, grabs Hiccup by the neck, and pins him to the ground. Toothless stares frighteningly at Hiccup, and the boy prepares for the worst. Toothless rears back, but instead of killing Hiccup, he roars loudly at him and then tries to fly lopsidedly out of sight. Toothless' sparing of Hiccup was unbelievable, and Hiccup soon realizes that the idea of dragons "Always go for the kill" is wrong.  Toothless finds himself trapped in the cove. He is unable to fly and therefore unable to escape. Hiccup sees him attempting to catch fish but failing. Toothless hears Hiccup dropping his pencil and notices Hiccup watching him, but remains passive.

Hiccup later returns, and Toothless is waiting on him. He has perched himself on a high rock, and he watches as Hiccup looks around for him. Toothless reveals himself, and does not attack Hiccup, though he growls in suspicion and distrust. Hiccup tosses his dagger away, and then offers Toothless a fish he has brought. The hungry Dragon drops his frightening attitude, and much to Hiccup's surprise has no teeth. Hiccup soon discovers that Toothless does indeed have teeth when the Dragon lunges forward and snatches the fish.

Toothless gulps the fish down in moments and then looks to Hiccup hoping for more. Hiccup backs away as Toothless approaches and tells the dragon that he has no more. In response to this, Toothless regurgitates half of the fish into Hiccup's lap, deciding to "share" with him. Toothless manages to get Hiccup to eat a bite of the revolting, raw, regurgitated fish. Hiccup pretends to enjoy it, though he can hardly disguise his disgust. He smiles at the Dragon, and Toothless is curious about the mannerism. Toothless pulls his face into a confused and comical looking attempt at a smile. Hiccup is awestruck at the Dragon's intelligence and personality. Hiccup reaches out to try and touch Toothless, but Toothless is not interested in the offer and flies to the other side of the cove.

Hiccup tries to touch him again when he lays down, but he quickly decides against it when he realizes he is aggravating the Dragon. Toothless rests for several hours, and then upon waking, notices Hiccup is still in the cove. He walks up and sits next to Hiccup who is drawing in the dirt. Toothless curiously looks at the picture of himself that Hiccup is scratching out with a twig and then stands up, walks off, and pulls up a small tree. Once again to Hiccup's utter astonishment, Toothless draws a maze of squiggles and lines in the dirt that were most likely meant to be a drawing of Hiccup before sitting down to proudly admire his work. Hiccup tries to step out of this maze, but Toothless is displeased when he steps on the lines. Hiccup realizes this and walks distractedly though the maze avoiding all the marks Toothless has made.

He finds himself right up against the dragon. Hiccup reaches forward, and Toothless gives him one last skeptical growl. Hiccup recoils, but only for a moment. Hiccup then closes his eyes trusting Toothless with his outreached right hand. The Dragon senses this trust, and is just as amazed with Hiccup as Hiccup had been with him. Toothless leans his head forward and touches his snout gently to Hiccup's hand. The two bond for a moment, and then Toothless rushes off yet again, leaving Hiccup to try and take in the depth of the moment.

Hiccup later begins to work on a new tail fin for Toothless. The first flight they have, Toothless is extremely excited to be airborne again, but he is not keen on having a rider. He tosses Hiccup off but only then realizes that the tail-fin will not work unless Hiccup is operating it. Hiccup designs tail-fin after tail-fin, and each attempt brings the boy and Dragon closer. In between flight tests, Hiccup discovers more and more of Toothless's playful and curious nature. He uses his new found Dragon knowledge to his advantage in the ring. Because of this, Hiccup becomes remarkably popular, which angers Hiccup's training companion and secret crush, Astrid.

Still Hiccup finds himself to be much happier being around Toothless than being around the other teens, and the boy and Dragon are soon extremely close friends. By the time they do their first real test flight, Hiccup and Toothless are mostly in sync. Hiccup still has a little trouble with the tail movements, but when he accidentally falls off, he and Toothless are put onto a crash course into a huge array of rocks at breakneck speed. The two then snap into focus with one another, and they blast through the rocks swerving, ducking, and doing barrel rolls.

The flight is a huge success and both Hiccup and Toothless are ecstatic over it (until Toothless accidentally burns Hiccup). They share a meal with each other afterwards, and Toothless again tries to give Hiccup regurgitated fish. Hiccup declines, but a small group of Terrible Terrors arrive and try to steal Toothless's fish. Toothless foils their plans and eats his fish himself. This angers one of them enough to get it to try and breath fire at the Night Fury. Toothless gives the creature a snide look and then shoots a plasma blast into its open mouth, causing its own fire gasses to backfire into itself. Hiccup notes that Dragons are "not so fire proof on the inside" and then kindly gives the Terrible Terror one of his own fish. Hiccup soon sees that everything the Vikings know about Dragons is wrong.

When Hiccup unknowingly leads Astrid to the cove, Toothless shows his protective side by assuming that she is a threat. Only through Hiccup's words does he manage to calm down enough, although still being wary.

When Astrid threatens to tell the village, Toothless and Hiccup abducts her and strands her on a tree to stop her. Even though Hiccup invites her to a flight to show Toothless is not dangerous, the Night Fury isn't convinced that she can be trusted and pulls off daring acrobatic moves (corkscrews, loop-de-loops, etc.), not to throw her off, but just to terrify her (which indicates that he may not be as dependent on Hiccup for flying as first assumed).

After she apologizes, Toothless begins to trust her more and assumes she's now a friend, smoothing out his flight. He gives both Astrid and Hiccup a beautiful, romantic "Dragon's eye view" of Berk. The beauty of the moment breaks Astrid's long held beliefs about Dragons, and she admits that Toothless is simply amazing.

Unfortunately, Toothless's old ties to the Dragon society make a frightening return. Toothless flies into a fog bank with both teens on his back. They find themselves in the middle of a huge flock of Dragons that are carrying great amounts of carrion and food. Hiccup thinks the Dragons are hauling in their kill and Astrid nervously wonders whether Toothless intends to haul them in with the rest. Toothless and the Dragons zig-zag through the fog until they reach a giant volcanic mountain.

The Dragons dive into a series of tunnels in the side, and Hiccup and Astrid soon find themselves flying above a massive cavern filled with red smoke. The dragons drop hundreds of dead animals into a huge hole in the middle of the cavern. Toothless looks nervously down into it before landing. He continues to look tensely around until a lone Gronckle donates a single fish. This provokes the monstrous Red Death to emerge from the hole and devour it. Astrid and Hiccup are both in shock, and Toothless soon sees that he too is in danger. The Red Death has noticed his lack of contributions, and he lunges at Toothless who barely swoops out of the way. While flying away with all the other Dragons, the Red Death sadly managed to catch the tail of an unfortunate Zippleback with its jaws and pulled it back.

Toothless then rockets out of the mountain along with the entire herd of terrified Dragons. Upon returning Toothless takes a long drink from the pond while Hiccup and Astrid try to make a plan. After Astrid kisses Hiccup on the cheek and leaves, Toothless walks up and gives Hiccup a happy but teasing look.

Toothless senses another threat the next day when he hears Hiccup screaming from afar. Realizing he is in danger, Toothless manages to claw his way out of the cove (for the first time on his own) and immediately rushes to Hiccup's side to protect him from the Dragon he is supposed to kill. He refuses to leave his friend's side when the Vikings eventually get in on the fight and gang up on him, managing to fight them off and have Stoick at the mercy of his flames. Only when Hiccup yells at him to stop does he let his guard down long enough to be captured.

Toothless is chained up and used as a compass to reach the Dragon's Nest. However, as he observes the other Dragons flying away, he begins desperately trying to free himself as The Red Death suddenly bursts out of the Nest. The ship he's chained to is set alight, and he is thrown into the water when the ship breaks up. Hiccup dives into the water in a desperate attempt to free Toothless, but passes out from lack of air. Just then, Stoick dives in to save Hiccup first, then he dives back in to break Toothless free, to which Toothless grabs Stoick to swiftly take him back out of the water.

Hiccup then mounts Toothless and they both fly into the air to take down the Red Death. The two soon have the enormous dragon chasing them into the clouds, where while the Red Death loses sight of them, Toothless blasts holes through the Red Death's wings. As the Red Death then blows fire everywhere in the sky, Toothless' prosthetic tail-fin catches fire, and Hiccup and Toothless decide to dive towards the ground, with the Red Death still chasing after them, during which the enormous dragon prepares to finish them off by charging a most powerful fiery blast. Just as they are closer to the ground, Toothless fires one more plasma blast into the Red Death's mouth, and he and Hiccup fly upwards to escape as the Red Death crashes to the ground and destroyed in a fiery explosion.

While escaping a fireball from the explosion, Hiccup and Toothless get struck by the Red Death's tail, resulting in Hiccup getting knocked off from Toothless' back and free-falling into the fireball. Seeing his human friend falling to his fiery death, Toothless bravely dives into the exploding body of the Red Death to save Hiccup, wrapping him in his wings to protect him as they land, showing that Toothless's bond with Hiccup is very strong indeed.

A little later, Toothless is overjoyed when Hiccup wakes from the battle, licking him in the face playfully, like a pet would, knocking all sorts of things over while jumping around Hiccup's home happily, and helps him to walk with his new prosthetic leg as a sign of their friendship. Having both lost a part of their body by the end of the movie, this makes Hiccup and Toothless symbiotically equal. Toothless gains a new tail-fin at the end of the film, given to him by Gobber, and takes off into the skies with Hiccup once again.

## Abilities and Skills

Toothless displays a huge variety of abilities throughout the movie franchise. Toothless has been trained by Hiccup very well to learn these great skills, though many are natural.

* **Intelligence and Communication Skills:** He is extremely intelligent and can almost completely understand everything said to him. He also seems to be able to command other Dragons to an extent. He is an incredibly strategic thinker. Hiccup and Toothless work together to cripple the Red Death and then use his fire against her. Also, when Toothless is captured and imprisoned by the Outcasts in We Are Family Part II, he manages to outsmart the guards on his own. He tricks them into thinking he is unconscious so as to get them to remove his muzzle. It is a surprisingly clever plan, and it completely fools the Outcasts. Toothless also seems to be one of the few dragons who attempts to show creativity. Toothless has been trained, by Hiccup, to comprehend silent commands via hand signals and motions, such as "Battle-ready", "Plasma Blast", "Smile" and "Search". He has also been taught by Hiccup, to recognize his riders Night Fury Call as a summon. Toothless also mimics Hiccup, such as in the second movie at the Itchy Armpit.
* **Speed and Acrobatics:** He is the fastest flier among the Dragons, with the Skrill second and Typhoomerang third. The Art of How to Train Your Dragon book notes that he can fly over one hundred miles per hour. He keeps up with Hiccup easily in a free fall, and humans reach terminal velocity at around one hundred and fifty miles per hour. He is the only Dragon so far to be able to do a vertical takeoff. Even when not flying he can tear along the ground at terrific speeds. His jumping abilities are phenomenal. It was demonstrated several times he has a very flexible body. Toothless have shown possessing remarkable agility in flight as well as on land. In HTTYD 2 he is able to dodge several nets that were aimed for him with great nimbleness and reaction time. He is very likely one of the most agile Dragons on land and was shown being able to leap from trees, boulders, walls, etc. Valka demonstrated that the fins on his back can split into another set of fins, making Toothless even more aerodynamic and better at mastering tight turns. Toothless was able to fly blindfolded during his fight with Drago's Bewilderbeast.
* **Strength:** Toothless has shown to be very strong for a Dragon of his size, as he has been seen defeating Dragons bigger then him, such as Monstrous Nightmares and Whispering Deaths. He managed to defeat Hookfang in a short, but brutal fight. He can even push back Hookfang by using all his four legs. He was also able to throw away a full-grown Whispering Death. He has been seen carrying heavy objects, such as boulders and barrels with his front legs. He can also carry adult Vikings, such as Stoick and Alvin with the small extra weight of Hiccup on his back. He was able to carry Stoick, who weighs 400 pounds, for an entire day before getting completely exhausted, although he found this very tiring and was unwilling to repeat it. He also has been seen carrying the Lead Stinger in his mouth, and prevented Barf and Belch from flying after the Dragon Root by holding his tail. As a Strike-class Dragon, Toothless has a vice-like jaw that can exert great force.
* **Endurance and Stamina:** Toothless can fly longer than any other Dragon at least bit longer, but he was shown to be exhausted in the episode View with the Skrill part 1, but unless he has to carry heavy objects or someone heavy. He has shown to be able to run long distance with no sign of being exhausted from the cove to the kill ring, that he can also able to take a lot of damage in battle from Hookfang, fighting off the berk warriors, and Stoick the Vast. He can take attacks from hisrival, and still look untouched.
* **Retractable Teeth:** As a Night Fury , Toothless has the ability to retract his teeth. This unique trait can make him appear to be toothless, hence his name.
* **Senses:** He is shown to have an uncannily great sense of hearing. He is able to hear Hiccup's cries for help all the way from the cove even when Hiccup is in the arena. This good sense of hearing plays into his ability to use a sonar. He is seen using it in the film in order to locate Dragon Island. He tracks Hiccup by his sense of smell throughout We Are Family Part II, but loses him when Hiccup takes to the air on the back of a Deadly Nadder. He also seems to have the ability of night vision.
* **Stealth and Camouflage:** Toothless' black scales and extreme speed make him hard to notice, especially at night. This was demonstrated when confronting the Flightmare.
* **Plasma Blast:** Toothless is also able to shoot several forms of fire (see Fire Types). His signature attack is dive bombing where he dives at great speed and then fires a precise and very powerful blast. It is strong enough to destroy a catapult and even knock down the Red Death while making the ground shake a little and sending slight but noticeable shock-wave. He can also weaken his blasts enough to use them for non-violent purposes (like knocking people out of trees).
* **Saliva:** Oddly, Toothless' saliva actually has an incredible amount of healing properties. However, this was only stated in *Defiant One* to heal Snotlout's tongue after eating some strange berries. It is possible Hiccup made this up and the effect of the berries wore off. Hiccup also stated that Toothless' saliva doesn't wash out. It is also proven to be an effective adhesive, more than human saliva, as shown when Hiccup uses it to stick together parts of his map.
* **Echolocation:** In We Are Family Part I, it is revealed that Toothless has a hidden ability that Hiccup never known about it, being so long with Toothless he finds a strange ability that Toothless can use; an echolocation to guide himself and Hiccup out of the cave they were trapped in. Hiccup recalls later that "Toothless let out a weird sound that bounced back toward them, and was able to use that to get out". He also used this ability in "Frozen" when they are flying over the frozen sea.
* **Swimming:** Toothless is a great swimmer, and has saved Hiccup from drowning several times in the process. He has also been seen sea skimming from one island to another.
	+ **Sea skimming:** A particular way of swimming that, according to Hiccup, "it's like flying... but not." To perform this, Toothless dives and jumps out of the water continuously. This ability doesn't require for Toothless to be ridden by anyone, he can do this all by himself.
* **Synchronization:** Thanks to the time they used the prosthetic tail-fin, Toothless and Hiccup are able to fly together in perfect sync. Not only that, but they also understand each other the best out of all Dragons and riders, which was demonstrated several times.
* **"Flaps" on back:**  Toothless' hidden ability, that was unknown even to himself. Revealed by Valka, those leathery flaps are flat fins-like spikes, placed in "V" shape and extending from his back, to the end of the tail. They gave him more maneuverability and control in flight, almost like a second tail.
* **Titan Wing/Alpha Mode:**  Toothless is able to "charge" himself in some way, it gives him more strength, stronger fire with seemingly no limit, and the ability to not only withstand an Alpha's control, but command other dragons as well. This also gave him the more menacing look, with back, nose and mouth glowing blue color similar to his fire, probably because of amount and strength of this fire inside Toothless. This gave him the ability to challenge the Alpha and stand his own against it. It also gave the Night Fury species to become an Alpha Species, enhancing the power of Toothless made him able to defeat the Bewilderbeast.

## Relationships

### Hiccup Horrendous Haddock III

Toothless is Hiccup's best 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 power. The two of them have become extremely close, and their bond of friendship has survived many a harsh trial. Both Toothless and Hiccup have made serious mistakes while dealing with each other.

Hiccup would not heed Toothless' warnings in The Terrible Twos, and Toothless would not allow Hiccup to aid him the battle with the Whispering Death in What Flies Beneath until Hiccup forced him into a position where he had to either save Hiccup or continue his vendetta. Even with these two extremely trying and difficult events, Toothless and Hiccup quickly reconcile, and together they overcome even the greatest challenges.

When Hiccup and Toothless first met, they were merely curious about each other, but eventually this curiosity caused them to see each others similarities. They bonded in the cove, and Toothless would grow in his loyalty to Hiccup as he and the boy became more and more familiar with each other. Hiccup would soon allow Toothless to fly again, and in doing so he would give the Dragon back the thing he held most dear. Toothless and Hiccup often fly together. They have spent hours in practice, and both seem perfectly happy to stay airborne as long as possible. Gobber remarks how hard it is to get Hiccup off of Toothless, and he holds a fair point.

The boy and Dragon clearly like nothing more than flying through the rushing air as one. By the time of Snoggletog, Toothless is actually far more interested in his friendship with Hiccup than his own freedom. He is given the ability to fly on his own, but he is so determined to never leave Hiccup that he destroys his new auto-tail. In essence he very much wants to need Hiccup. Toothless is fully willing to risk his own life for the sake of his friend.

He attacks Hookfang and fends off many a Viking trying to protect him in the movie. Toothless would eventually dive into the exploding body of the Red Death in order to save Hiccup's life. In the events of When Lightning Strikes, after Hiccup is hit by a lightning bolt, Toothless' strong bond with Hiccup is displayed yet again when he breaks free from a restraint that he couldn't free himself from in the film and dives into the water after Hiccup. The two of them are always together and have become practically inseparable. Toothless follows Hiccup everywhere and enjoys the company of Hiccup even in the most mundane and normal daily activities. Toothless seems to be perfectly happy with Hiccup even though he has no other Night Furies.

Astrid notes that Toothless does not seem to need anyone besides Hiccup to make him happy, and this is very often shown to be true. In The Night and the Fury, Tuffnut refers to Hiccup as Toothless' "other half." Toothless' position as Hiccup's first and best friend is never questioned, with Hiccup referring to him as the best friend he has ever had. Even after Toothless was briefly brainwashed by Drago's Bewilderbeast to kill Stoick, after Hiccup initially yelled at Toothless out of grief and pain, he soon calmed down, breaking through the Alpha's control of his friend by assuring Toothless that he didn't blame him for what had happened. Toothless in return challenged the massive Bewilderbeast solely through his desire to protect Hiccup, showing that their bond is unbreakable even in the toughest of trials.

### Stoick the Vast

Toothless and Stoick got off to a really bad start from the moment they first meet. Stoick charges Toothless, seeing him as the ultimate threat to the island and the very "Unholy Offspring of Lightning and Death itself". Toothless responds by singling Stoick out among all the other Vikings who are trying to capture him. He clearly sees Stoick as the greatest threat and he tackles him, thinking that Hiccup needs to be protected. Stoick struggles, but even with his massive strength he is unable to keep Toothless from pinning him to the ground. Toothless prepares to kill Stoick with a fire blast, but Hiccup screams "NO!" in utter despair and desperation.

Toothless stops, and the Vikings quickly capture him. Stoick is outraged at Hiccup for training Toothless but soon discovers that Toothless can be used to find Dragon Island. He chains Toothless in a cruel harness and sails off with him. Toothless unwillingly leads the entire Viking fleet to the island, but they are attacked by the Red Death and soon the ship Toothless is chained to is set on fire. Stoick actually jumps into the water upon seeing that Hiccup was right about the Dragon, and he tears Toothless free of the harness. After the battle, Stoick believes Hiccup to be dead. He apologizes to Toothless in painful grief, but Toothless reveals that Hiccup is still alive.

Stoick deeply thanks the Dragon for saving his son, and the two of them grow to have great respect for one another. In general, Toothless continues to respect Stoick as an authority figure. He allows Stoick to ride him during How to Pick Your Dragon even though it causes Toothless great discomfort, and rather than confront Stoick in a negative reaction to dissuade the chief from riding him again, preferred to hide instead. Stoick stands up for Toothless without hesitation in When Lightning Strikes. Stoick's and Toothless' friendship is fairly strong, and it is made even stronger by their mutual love for Hiccup.

In *How to Train Your Dragon 2*, their relationship is stronger. Toothless appears to agree with Stoick's decision not to go after Drago in the beginning. When the duo takes off in the dragon hanger, his roar might have been a warning to the chief of Hiccup's plan to go against his orders. Toothless also assists Stoick when he asks Valka to come back to Berk. Near the climax, Stoick is killed by a mind-controlled Toothless' plasma blast to the chest. Upon temporarily being freed from Drago's Bewilderbeast's control, Toothless comes to his senses, and approaches Stoick's body, not knowing what he did until Hiccup forces him away. Realizing his action, Toothless is saddened and in remorse for what he had done while under the Bewilderbeast's control, but redeemed himself for this incident by challenging and defeating the dark Bewilderbeast.

### Astrid Hofferson

Toothless' first impression of Astrid is a very bad one. He sees her hurting Hiccup and decides she is a threat. He leaps towards her and prepares to land on her with mouth agape. Hiccup jumps in and pushes Astrid to safety and disarms her at the same time.

He tries to calm Toothless down, but the Dragon can barely control his rage. Astrid is introduced, but Toothless is not amused. Astrid then runs to try and tell Stoick, but Toothless and Hiccup abduct her. Hiccup convinces her to ride Toothless claiming that there is nothing to be afraid of, but Toothless has other, less friendly, ideas. He leaps into the air and pulls off an array of dangerous aerial maneuvers. Astrid is terrified into apologizing, and Toothless smooths out his flight.

He then gives her an amazingly beautiful view of Berk from the air. She is amazed by the splendor of the scene and admits that Toothless is amazing. From that moment on, she helped Hiccup try and keep Toothless concealed. Toothless saved her from being eaten by the Red Death, and upon doing so gave her a big toothless smile.

Astrid, like all the other Hooligans, is incredibly relieved to see that Toothless saved Hiccup. Toothless seems to have a good grasp on Hiccup's crush on Astrid, and he even teases Hiccup about it momentarily. Toothless continues to like Astrid, but her competitive nature occasionally annoys him. He is determined to stay on top of her and Stormfly, but the competition is friendly, and Toothless never seems to be uncomfortable around Astrid. He has gotten used to her violent "communication" methods and does not seem to mind her hitting Hiccup. He does openly wince at time when she punches, kicks, or arm-locks Hiccup. Still, as with Stoick,Valka and others, Toothless seems to greatly trust Astrid and appreciate her friendship and love towards his rider.

### Gobber the Belch

Gobber was the one who made Toothless' new tail-fin. The old Viking also understands Toothless, and Dragons in general, which was seen in 'The Terrible Twos' when he gave Hiccup advice about Toothless' odd behavior.

### Stormfly

In the books, Toothless has a huge crush on Stormfly, and often brags to her. Stormfly seems not to care, but stays mostly by his side during How to Ride a Dragon's Storm. In How to Seize a Dragon's Jewel, Toothless blushes upon seeing Stormfly, telling her that he is "Toothless the Outcast", and points out the Wodensfang, telling her that his "sidekick, Wodensfang the Desperado."

In the movie and franchise, Toothless and Stormfly share a mysterious but pretty close friendship. They seem to enjoy each other's company, and occasionally they can be seen interacting with each other on friendly terms. Toothless seems to wish Stormfly farewell when she leaves in Gift of the Night Fury or she was telling Toothless to come with her. They are not always friendly, however. Often times Astrid's competitive nature can be seen in Stormfly, and that means that she and Toothless do occasionally get competitive. It is usually all in good fun, but sometimes the competitions can get a little out of hand, as when they were Dragon boarding in Animal House.

Toothless' friendship in Stormfly is probably aided significantly by the fact that Stormfly's rider is one of Hiccup's closest human friends. Not much is really known about their friendship, but it seems too be friendly smooth and can be a little competitive at times. In *How to Train Your Dragon 2*, they are seen playing and talking to each other in a friendly manner, while Astrid and Hiccup are having a conversation. Their close bond is also hinted at when Toothless breaks free of the Alpha's control and calls other Dragons to aid him, with Stormfly being the first Dragon shown to return to herself and join Toothless as he makes his stand. After the Bewilderbeast's defeat, Stormfly acknowledged Toothless as the new Alpha Dragon by bowing down to him.

### Valka

Toothless appears to like Valka, probably because she is close to his rider, Hiccup. Like Hiccup and Stoick, Toothless was also wanted her to come back to Berk. Toothless plays with her and understands that she is Hiccup's mother. Valka and Toothless also share a mutual love for Hiccup.

### Nightstar

Toothless also share a really close relationship with Yuna's Night Fury, Nightstar. As they flew by each other they came to like each other and soon become lovers. In the episode:The Gifts of 2 Night Furies Part 1, Thoothless and Nightstar's main relationship is really shown. In which they have seven Night Fury hatchlings. They will often work side-by-side and help each other out. Toothless really cars for Nightstar and will do anything to protect her.

## Current Enemies

### Dagur the Deranged:

Toothless shows more of his ferocious side whenever he sees Dagur, since he is obsessed with killing Dragons.

### Drago Bludvist:

Like all Dragons, Toothless has a deep hatred for the self-proclaimed "Dragon God." Drago used Toothless, by the Bewilderbeast's control, to attack Hiccup, but ultimately killed Stoick instead. Drago rode Toothless to Berk until Hiccup freed his Dragon partner and defeated the mad man together.

### Drago's Bewilderbeast:

Like other Dragons, Toothless fell victim of the Alpha's hypnotic abilities and was forced to attack Hiccup, but ultimately killed Stoick instead. When broken free and the large Dragon attacked Hiccup directly, Toothless used his body to shield him from the icy blast. Toothless then challenged the Alpha and defeated him by having the other Dragons join him and destroyed his left tusk, becoming the new Alpha, redeeming himself for his unintentional hand in Stoick's demise, and gaining his innocence back.