Toothless
Name:	Toothless
Race:	Dragon
Species:	Night Fury/Common or Garden Dragon
Rider:	Hiccup
Gender:	Male

"I wouldn't kill him because he looked as frightened as I was. I looked at him, and I saw myself." - Hiccup in "How to Train Your Dragon" (movie)

Toothless is the name of Hiccup's dragon in both the book series and film. In the books, Toothless is a Common or Garden Dragon, while he is a larger black Night Fury in the film adaptation. In the film, he is the first dragon ever to be trained and serves as one the most major characters in the franchise. He is the quintessential dragon in the series, and remains unrivaled in both speed and intelligence.

Contents 1 In the books 1.1 Physical Appearance & Personality 1.2 Role in the books 2 In the Film Franchise 2.1 Physical Appearance & Personality 3 Role in the Film 4 Role in Gift of the Night Fury 5 Role in Dragons: Riders of Berk 6 Abilities and Talents 7 Relationships 7.1 Hiccup 7.2 Stoick the Vast 7.3 Astrid Hofferson 7.4 The Whispering Death 7.5 Hookfang 7.6 Stormfly 8 Garden Dragon to Night Fury 9 Trivia 10 Gallery

In the books

Toothless is Hiccup's hunting Dragon in the book series, who likes to cause mischief when he can.

Physical Appearance & Personality

Toothless is much smaller than any of the other young Vikings' dragons. He is the most common breed of dragon - Common or Garden, and as his name suggests, he has no teeth. He is portrayed as being a dark green color with red membranes in his wings. He is also small enough to sit on Hiccup's arm with relative ease. Toothless is incredibly disobedient, and like all dragons very selfish and ungrateful, he is nonetheless quite attached to Hiccup. However, Toothless' behavior does have its drawbacks, especially when he manages to cause the entire young generation of the Hairy Hooligans to be forced into exile by starting a fight at Thor's Day Thursday celebrations.

To prevent Hiccup's father from being furious over how small and average his son's dragon is, Hiccup's best friend Fishlegs comes up with a legend that Toothless is not a Common or Garden dragon, but is, in fact, a very rare breed called Toothless Daydream and is possibly an offspring of a great dragon leader King Daggerfangs. From then on, Toothless always claims that legend to be true.

Role in the books

At the eastern coast of Berk is an area known as Wild Dragon Cliff, Hiccup uses a dragon basket to capture a dragon for himself. Fishlegs escapes the area without a dragon, meaning he is at risk of exile. Hiccup runs back in to the cave to get another for him and the two leave with a dragon each (Horrorcow and Toothless).

After returning home, Hiccup attempts to train Toothless based on advice from Gobber, but this turns out to be problematic as Toothless' disobedience causes Hiccup's many attempts to fail, eventually forcing him to resort to pampering. During practice for hunting with Fishlegs, Toothless finally agrees to be co-operative on the condition that he is told one joke for every fish he catches.

On Thor's Thursday, during the final part of the rite of passage, Toothless offends Fireworm (Snotlout's dragon) and there is a huge fight between them all. This means that the younger Vikings have all failed their rite and will be exiled. However, it is not long before 2 giant Sea Dragons arrive with a storm and Hiccup is turned to for help to speak with the dragon. When Hiccup tells the Elders of the remaining dragon's plan to eat them all, Hiccup decides to use this time to gather the boys and their dragons together and come up with a plan to stop the Green Death from killing anyone. Toothless decides not to go along with this as he thinks the plan is suicidal and he dislikes the giant dragon a great deal.

The plan seems to be working until Hiccup is swallowed whole by the Green Death. When Toothless sees that all the wild and domestic dragons have left out of fear, he concludes Hiccup is his only remaining family and saves him by making the Green Death sneeze. Hiccup eventually makes the dragon explode, causing him to pass out.

Three hours pass and Hiccup wakes up to find that Toothless has "died" from his wounds. Hiccup correctly guesses he is only in a coma and goes to save him from being burnt at a traditional Viking funeral. Hiccup is recognized as a hero for his efforts and Toothless is saved from the fire.

In the Film Franchise

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.

Physical Appearance & Personality

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 at three 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, lost when Hiccup takes Toothless down with his Bolas-Shooting Ballista. This is later replaced by a mechanical fin that Hiccup constructs himself. Toothless' eyes are a yellowish-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 two wings that aided in steering and stability, but his left one is now missing.

He proves himself to be a very able 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 does not take kindly to being offended or 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 is highly unintimidated by Astrid and walks off with a sort of shoulder shrug and eye roll when she threatens to expose Hiccup's and Toothless' friendship to Stoick. He certainly displays an independent attitude when he takes both Hiccup and Astrid on a rollercoaster 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 simply for the sake of taking off some steam. His attitude is usually hidden under his docile nature, but it comes out in comical ways from time to time.

Hiccup and Toothless share a nearly 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.

Role in the Film

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

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. 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 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 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 tailfin, 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 flies lopsidedly out of site. 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 unable to escape. Hiccup sees him attempting to catch fish but failing. Toothless notices Hiccup watching him, but remains unaggressive. 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 Hiccups surprise looks both toothless and cute. 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 Hiccups lap, deciding to "share" with him. Toothless manages to get Hiccup to eat a bite of the revolting, raw, and 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 canyon. 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 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 Hiccups 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 airborne again, but he is not keen on having a rider. He tosses Hiccup off but only then realizes that the tailfin will not work unless Hiccup is operating it. Hiccup designs tail fin after tail fin, and each attempt brings the boy and dragon more into sync. In between flight tests, Hiccup discovers more and more of Toothless' 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 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 temporarily 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. 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' 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 bolt 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 give 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 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 is not 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 is now a friend, smoothing out his flight. He gives both Astrid and Hiccup a beautiful "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' 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 zigzag 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 him. 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. Toothless then rockets out of the mountain along with a whole 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 and thanks him, 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 screams at him to stop does he let his guard down long enough to be captured.

Toothless is chained up and used 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 both he and Hiccup are thrown into the water when the ship breaks up. Stoick, however, saves both of them and Toothless takes on the larger dragon with Hiccup by his side.

Toothless' bond with Hiccup is shown to be very strong indeed when his prosthetic tail fin is set on fire in the ensuing battle. When Hiccup is knocked off his back, Toothless bravely dives into the exploding body of the Red Death to save his human friend, wrapping Hiccup in his wings to protect him as they crash. Toothless is overjoyed when Hiccup wakes from the battle later, 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.

Role in Gift of the Night Fury

Toothless plays a major role in the short Gift of the Night Fury. Snoggletog has started, but the dragons all mysteriously disappear. Hiccup loses his helmet in a flight with Toothless, but the he returns to Berk because of the emergency of the sudden dragon evacuation. Later, Tuffnut points out that Toothless cannot fly on his own, so Hiccup feels guilty. He builds Toothless a new auto tail, but when Toothless receives it he launches off into the sky and leaves Hiccup. Much to Hiccup's relief, Toothless returns during the Snoggletog celebration and gives Hiccup the wonderful gift of a drool filled helmet. Hiccup is relieved to see him and Toothless receives a warm hug in thanks. 

Toothless gives yet another example of their incredibly strong friendship is in the short when Hiccup gave Toothless an auto-tail fin so he could fly on his own. In the end, however, although he used the tail fin to recover Hiccup's previously-lost helmet, Toothless threw his new tail fin away, and nudges the old fin and saddle set towards the young Viking, showing that Toothless would rather fly with Hiccup as opposed to just carrying him like all the other dragons. He sacrifices his freedom for the sake of a stronger friendship. He shows that he very truly wants to need Hiccup.

Role in Dragons: Riders of Berk

Hiccup and Toothless remain close in Dragons: Riders of Berk, with Hiccup once even planning to leave Berk with Toothless after Mildew convinced the other Vikings that Toothless- as the 'unholy offspring of lightning and death'- was angering Thor and causing various lightning storms (It was eventually revealed to be a metal statue and perches attracting the lightning). He practically never leaves Hiccup's side. They sleep in the same room and are often seen doing even simple tasks together. The two of them easily dominated the dragon events in the Thawfest games. Toothless appears to be rather a leader among the dragons. The only occasion where Toothless has defied Hiccup was when a Whispering Death that Toothless had fought in the past came to Berk, with Toothless attempting to fight his old foe on his own- even ordering the other dragons to stay away from him during the fight-, although he eventually accepted Hiccup's aid when Hiccup deliberately jumped off a cliff while Toothless was being attacked on the other side, forcing Toothless to save Hiccup and accept his help or let Hiccup die to continue his vendetta. When he, Snotlout, and Hiccup become stranded on Outcast Island, he is behind Hiccup one hundred percent even during the many arguments between the boys. He also manages to work together with Snotlout in order to save his captured rider. Toothless is also a central character, along with Hiccup and Mildew, in the season finale of Riders of Berk. He and Hiccup go off looking for more Night Furies. At first Toothless seems only slightly interested, but as they get closer and closer to their goal, both Toothless and Hiccup become extremely excited. Unfortunately it is a trap set by Alvin and Mildew, and both Hiccup and Toothless are captured. Toothless is locked into a high security cell in the Outcast dragon containment area. He proves his intelligence yet again when he escapes on his own. He fools the Outcasts into thinking that he is unconscious and sick. The Outcasts remove the muzzle from his mouth, and he immediately blasts them back and frees himself. For the rest of the episode he looks for Hiccup in Outcast Island. Outcasts are on his trail, but he annihilates them with his fire blast. This is notably more violent than he usually is with humans, but he is obviously more concerned, Hiccup is missing, and he is not going to hold back at all until he finds his owner. Toothless and Hiccup eventually find each other using dragon calls. They then both decide to attack Alvin when he appears and openly mocks Hiccup. Both boy and dragon usually refrain from "going for the kill", but Alvin has gone too far, and they dive for him. It is yet another trap, and they are both temporarily captured by bolas. The other teens' dragons swoop in and rescue them. Back in Berk, Toothless does look slightly saddened to see that the Isle of Night was a fake, but both he and Hiccup agree that there is nothing wrong with being one of a kind. The season ends with Toothless and Hiccup flying off into the horizon, confident that they will be there for each other in the battles that are yet to come.

Abilities and Talents

Toothless displays a huge variety of abilities throughout the movie franchise.

• Intelligent: 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. He and Toothless work together to cripple the Red Death and then use his fire against him. Also when Toothless is captured and imprisoned by the Outcasts in episode 20, 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. 

• Speed and Agility: He remains the fastest and most maneuverable of all the dragons in flight. 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. He and Hiccup work extremely well together and are practically in sync. Even when not flying he can tear along the ground at terrific speeds. His jumping abilities are phenomenal.

• Senses: He also has been shown to have an uncannily good 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 kill ring. This good sense of hearing plays into his ability to use sonar. He is seen using it in the film in order to locate Dragon Island. He tracks Hiccup by scent throughout episode 20 but loses him when Hiccup takes to the air on the back of a Nadder.

• Skilled Combatant: He is a very deadly opponent in battle. He has been seen defeating Hookfang, Stoick, a Typhoomerang, a Whispering Death (though only with Hiccup's aid), a wild Gronckle, and several Outcasts throughout the franchise. His large and powerful wings allow him to actually wrestle much larger dragons out of the air.

• Night Camouflage: He is extremely difficult to see at night due to his dark scales and blazing speed.

• Fire Blast: Toothless is also able to shoot several forms of fire (see Fire Varieties ). 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. This could explain why dragons "lick their wounds". 

• Echolocation: In the first part of the season finale of Riders of Berk, it is revealed that Toothless can use echolocation to guide himself and Hiccup out of the cave they were trapped in.

Relationships

Hiccup

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 vikingness, 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 Terrible Twos, and Toothless would not allow Hiccup to aid him the battle with the Whispering Death in What Flies Beneath. 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 other's similarities. They bonded in the cove, and Toothless would grow in his loyalty to Hicccup 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. Toothless' position as Hiccup's first and best friend is never questioned. Hiccup refers to him as the best friend he has ever had. 

Stoick the Vast

Toothless and Stoick get 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". 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 defended. 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. 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 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 destroyed. 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 the episode How to Pick Your Dragon even though it causes Toothless great discomfort. Stoick does stand up for Toothless in When Lightning Strikes. Stoick's and Toothless' friendship is fairly strong, and it is made even stronger by their mutual love for Hiccup.

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 smoothes 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 armlocks Hiccup. Still, as with Stoick, Toothless seems to greatly trust Astrid and appreciate her friendship towards his rider.

The Whispering Death

Toothless' arch rival is a Whispering Death from his past. He and this dragon have some sort of serious history, and they both are willing to fight to the death over the grudge. What the events were that started the feud are unsure, but the Whispering Death has a large bite mark from his previous battles with Toothless. This Whispering Death shows up in Berk looking for Toothless. The Whispering Death soon discovers that his old rival is unable to fly, and he uses that to his advantage. The Whispering Death refuses to be trained by Hiccup and nearly eats the boy. Toothless is nearly killed when the Whispering death attempts to blast him off of a cliff. Hiccup arrives just in time, and he and Toothless must work together to defeat this powerful enemy. Toothless had originally wanted to settle the score on his own, but Hiccup eventually convinced him to accept help. Whatever started the grudge was certainly serious. Toothless is so set on seeing the fight through that he actually fires a plasma bolt in front of Hiccup to get the boy to stop following him. Hiccup is deeply saddened by this, and Toothless realizes this, but he is still willing to hurt Hiccup's feelings for the sake of dealing with this past rivalry. Toothless cares for Hiccup deeply, so the fact that he would risk harming their friendship for the sake of revenge gives a tiny glimpse at the seriousness of his animosity towards this Whispering Death. In the end, Toothless spares the Whispering Death after defeating him. The Whispering Death then quickly retreats, and Hiccup is proud of Toothless for sparing his foe that had only moments before nearly killed them both. 

Hookfang

As far as can be guessed, Hookfang and Toothless met each other for the first time in the dragon killing arena. Hookfang was attempting to kill Hiccup, and Toothless blasted into the arena in order to save his friend. Hookfang and Toothless engage in a short yet brutal fight. Hookfang backs down, but shoots Toothless an odd look of contempt. Ever since, Hookfang and Toothless have never really seemed to get along. They tolerate each other most of the time.

Generally they simply avoid interaction. Occasionally they will get into fights, and when Hookfang went on a rampage, Toothless was quick to leap in and attack him. They share a sort of rivalry, and this is most clearly displayed in the Thawfest games. The dragons openly growl at one another before the games begin. Their relationship is not improved by the fact that Hookfang's rider, Snotlout, is often unkind to Hiccup. Toothless does not openly hate Hookfang, but there is very little evidence that either Hookfang or Toothless have any affection for one another.

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 loose 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. 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. 

Garden Dragon to Night Fury

The film's 'Terrible Terrors' were originally designed to be a more faithful take on Toothless' original book incarnation. As time went on in development however, it was decided that Hiccup's dragon in the film should have more presence and be able to stand toe to toe with his future tamer and lifelong friend and not just pairing the scrawny Viking with an equally scrawny dragon:

"Setting Toothless up as a threatening presence gave us that vital sense of tension for Hiccup's story,"- Chris Sanders (taken from -The Art of How to Train Your Dragon- pg.48)

Trivia

• In Book of Dragons, Hiccup states that he has never seen another Night Fury. This could indicate that Toothless is the last of his kind, or perhaps Night Furies are just few-to-none in the lands surrounding Berk.
• The similarities in the film's Toothless to Disney's Stitch (of Lilo and Stitch) are very prevalent, which isn't just a coincidence: The creative team behind the film version of How to Train Your Dragon (Chris Sanders and Dean DeBlois) is the very same duo behind Lilo & Stitch.
  • They are also canine-based and pet of the main character (Stitch being Lilo's "dog" and Toothless being Hiccup's pet)
• Toothless and Hiccup are shown to share traits of being very intelligent. Night Furies are the smartest dragons, and Hiccup is shown to be a smart Viking. In the Viking world, a Hiccup is the runt of the litter; in this case Hiccup is shown to be weak, but great at building, which made him an outcast.
• Hiccup claims that Toothless' saliva has healing properties in episode 16 in Riders of Berk. The spit does seem to heal Snotlout's swollen tongue.
• Toothless was shown hovering without Hiccup in Breakneck Bog, confirming that his tail injury merely stops him flying solo due to his lack of maneuverability rather than stopping him staying off the ground at all.
  • However, in What Flies Beneath, he can't fly when fighting the Whispering Death (Toothless's enemy).
• In some development concept art pictures Toothless resembles a Skrill or a Deadly Nadder.
• In When Lightning Strikes it is hinted that Toothless has a fear of lighting, due to his panicy behavior. This is ironic as Toothless is a Night Fury and Night Furys are the "Unholy offspring of lightning and death."

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