Toothless (HTTYD)

"I looked at him, and I saw myself." 
 ―Hiccup describing his relationship with Toothless.[src]
Toothless is the name of Hiccup Horrendous Haddock III's dragon in the How to Train Your Dragon franchise and the deuteragonist. Unlike his book counterpart, Toothless is a Night Fury, arguably the rarest and most intelligent of dragon species. He is the quintessential dragon in the series, and remains unrivaled in intelligence. He is presumed to be the only living Night Fury, at least on Berk and the surrounding Isles.
Having initially been shot down by Hiccup during a dragon raid, Toothless was nursed back to flying condition and became the Viking's best friend through their interactions and adventures. Following How to Train Your Dragon 2, Toothless is now a Titan Wing Night Fury.
Contents[hide]
 Biography
 Physical Appearance
 Personality
 Abilities and Skills
 Human Relationships
 Hiccup Horrendous Haddock III
 Stoick the Vast
 Astrid Hofferson
 Valka
 Gobber the Belch
 Snotlout Jorgenson
 Fishlegs Ingerman
 Ruffnut and Tuffnut Thorston
 Heather
 Dragon Relationships
 Stormfly
 Hookfang
 Meatlug
 Thornado
 Barf and Belch
 Rival Whispering Death
 Torch
 The Screaming Death
 Fanghook
 Skullcrusher
 Cloudjumper
 Windshear
 Shattermaster
 Sleuther
 Enemies, old and new
 Current Enemies
 Drago Bludvist
 Ryker Grimborn
 Viggo Grimborn
 Drago's Bewilderbeast
 Former Enemies
 Alvin the Treacherous
 Mildew
 Dagur the Deranged
 Temporary Riders
 Astrid Hofferson
 Stoick the Vast
 Fishlegs Ingerman
 Snotlout Jorgenson
 Ruffnut and Tuffnut Thorston
 Dagur the Deranged
 Drago Bludvist
 From Book to Film
 Trivia
 Appearances
 External Link
 Site Navigation
Biography
History Banner Default
Click here to view the biography of Toothless (Franchise).
Physical AppearanceEdit
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. However, when he is docile or happy, his pupils dilate and become more dog-like. Toothless gets his name from his sets of retractable teeth.
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Not so toothless
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.
As a Titan Wing, Toothless looks the same, but gains blue markings on his body, with those on his spines glowing, and he appears to have grown slightly larger.
In "Night of the Hunters, Part 2", Toothless wore armor made by Hiccup and Snotlout from the Screaming Death's scales. Despite being heavy, Toothless was able to avoid the Dragon Hunters arrows.
In "Snow Way Out", Toothless had lighter set of armor made from Gronckle Iron.
PersonalityEdit
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Toothless with his best friend and buddy, Hiccup.
Toothless is the most intelligent of all the dragons and seems to have a dry sense of humor, similar to Hiccup's. When Hiccup released him, he did not kill Hiccup. From here it was a little bit evident that he sensed goodness in Hiccup. He just had a few doubts due to which he did not let Hiccup near him for a few days.
He doesn't take kindly to being offended nor anyone offending or endangering his human friend but is usually playful and even a little teasing when not threatened. He shows a sense of great curiosity, imitating Hiccup's actions and mannerisms when they initially encounter one another and is 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 relationship with Astrid, even seeming to briefly tease him about it.
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Toothless stalks like a cat.
Toothless can display a bit of an attitude at times, reflecting his shared dry humor with Hiccup. He isn't easily intimidated and his daring bravado can get him into trouble at times. He is also not above using violence to reach an end unlike Hiccup, but will usually refrain when told to do so.
Overall, the biggest attributes of Toothless' personality come through in his relationship with Hiccup. Equally protective and loyal, he never hesitates to risk his own life when Hiccup is put in danger and is more than affectionate when the time calls for it. His sense of devotion also shows itself when protecting Hiccup's allies and other friends. Toothless has shown to have bit more of Hiccup's personality when battling Sleuther, seeing the fear in the other dragon's eyes, as it reminded him of when Hiccup did the same to spare him.
Toothless, although he cannot speak, shows a lot of emotions through his facial expressions and body language. Toothless has even been shown to make a laughing sort of noise, and often gives a few critical looks if he doesn't like the looks of something. 
Abilities and SkillsEdit
 Intelligence and Communication Skills: As a Night Fury, Toothless' intelligence is unrivaled amongst the other dragons and often displays the attributes of an incredibly strategic thinker. Toothless seems to be one of the few dragons who attempts to show creativity, as shown with his repeated attempts at drawing in both of the films. He is able to comprehend silent commands via hand signals and motions and has also been taught by Hiccup to recognize his riders Dragon Call as a summon. In Stryke Out he was able to trick a Razorwhip in the fights and understand how helpless the Triple Stryke was and decides to spare the dragon.
 Speed and Agility: The Art of How to Train Your Dragon book notes that Toothless can fly over one hundred miles per hour and his design reflects his status as the 'Ferrari of dragons'. His aerial acrobatics, though requiring Hiccup's help to pull off, allow him to escape rather brutal confrontations with little difficulty. Even when not flying, Toothless can tear along the ground at terrific speeds and is one of the most agile dragons on land, shown being able to leap from trees, boulders, walls, etc.
 Strength: Toothless has shown to be very strong for a dragon of his size, able to hold his own against other larger dragon species such as the Monstrous Nightmare, Whispering Death and Razorwhip. He can carry heavy objects, such as boulders and branches with his front legs alone and can also carry adult Vikings such as Stoick and Alvin on his back. While carrying Hiccup on his back he was also able to carry Hookfang with the extra weight of Snotlout with little struggle, and catch Barf and Belch when they fall off a cliff. 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. But he was shown to be exhausted during the first search for the Skrill, and carrying heavy objects or someone heavy like Stoick for a while day. 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 his rival, and still look untouched. After he was poisoned by the Triple Stryke he was still able to fight and defeat him.
 Retractable Teeth: As a Night Fury, Toothless has the ability to retract his teeth when not using them. This unique trait can make him appear to be toothless, hence his name.
 Senses: Toothless appears to have an uncannily great sense of hearing, able to hear Hiccup's cries for help from the cove even when Hiccup is in the arena as even possible can hear a small bug like a fly buzzing far in the distance. 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, 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 though Hiccup did question when flying in the dark cave so possibly his vision isn't that strong in the dark. He is however able to echolocate like a bat; sending sounds off and listening for them to bounce off objects around him, giving him the ability to find his way around in the dark. However the good sense of hearing can often be used against him though, making him relatively easy to control and influence from the call of a Red Death or Alpha dragon.
 Stealth and Camouflage: Toothless' black scales and extreme speed make him hard to notice, especially at night. This was demonstrated when confronting the Flightmare.
 Fire: Toothless is able to conjure several forms of fire. His signature attack is dive bombing and firing a precise and incredibly powerful blast, strong enough to destroy catapults and even knock down a Red Death in a single shot. He can also weaken his blasts enough to use them for non-violent purpose and this level of control also allows him to ricochet his shots off of other surfaces like cliff faces.
 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 extremely explosive 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). This level of control also allows him to ricochet his shots off of other surfaces like cliff faces.
 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 looking for Johann's ship. He can when use it to see in clouds, which he fits when looking for the Skrill.
 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.
 Dominance Display/"Titan Wing/Alpha": After being sufficiently enraged by Drago's Bewilderbeast, Toothless was able to "charge" himself in some way, it gives him more strength, stronger fire with seemingly no limit. 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 him. In this state, he challenged the Bewilderbeast. Dragons: Rise of Berk calls this glowing effect Toothless's Titan Wing stage, while School of Dragons calls it his "alpha" look, indicating the franchise is unsure what to call this effect. It is also shown that Toothless, when in Alpha mode, can ignore the Alpha. Even when he is not in Alpha mode, Toothless only needs a blindfold over his eyes and side ears and then he can ignore the Alpha.
Human RelationshipsEdit
Hiccup Horrendous Haddock IIIEdit
 Main article: Hiccup and Toothless' Relationship
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Toothless and Hiccup in flight
 "Please, you are my best friend bud. My best friend." 
 ―Hiccup trying to free Toothless from Drago's Bewilderbeast.
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, hiccup prepared to cut out Toothless's heart but was unable to follow through. Ever since then, 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.
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Toothless dives to save Hiccup
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 attack 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.
Hiccup and Toothless with their heads touching
A sweet moment
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.
In The Zippleback Experience, Toothless is shown to be able to sense when Hiccup is in danger, as he intensely looked out to the sea when Hiccup was captured by the Dragon Hunters, despite not being present when it happened.
Stoick the VastEdit
 "Thank you for saving my son." 
 ―Stoick, to Toothless who has brought Hiccup back alive
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Stoick thanks Toothless for saving Hiccup
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". Initially seeing Stoick as the greatest threat when 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 desperation. After that he chains Toothless in a cruel yoke to find the Nest, after discovers that Toothless can be used to find Dragon Island. the dragon is surprised when Stoick jumps into the water to free him upon seeing that Hiccup was right about dragons. After the battle of the Red Death comes to a close, 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.
During the TV series, Toothless continues to show respect for Stoick due to his status as the chief, but occasionally comes into conflict with his interests when the Viking's stubborn nature comes into play. Rather than face him outright, Toothless would rather avoid confrontation altogether even at his the cost of his own discomfort, such as in How to Pick Your Dragon. 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.
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A concerned, confused Toothless, nudging Stoick's hand
In How to Train Your Dragon 2, their relationship is definitely stronger as Toothless appears to agree with Stoick's decision not to go after Drago in the beginning. Upon seeing how happy the chief is when reunited with Valka, he tries his best to perform actions of encouragement for the whole family. Near the climax, Stoick is killed by Toothless' plasma blast when Drago's Bewilderbeast takes control of him. Upon temporarily being freed it, 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 for what he has done, but redeems himself for this incident by challenging and defeating the Bewilderbeast for Berk near the end.
In Burning Midnight, Toothless is shown to still bear some guilt over Stoick's death.
Astrid HoffersonEdit
 " (..) I'll need to fly Toothless since you'll be too busy." 
 ―Astrid's reaction to Hiccup becoming the new chief of Berk[src]
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Toothless meets Astrid
Toothless' first encounter with Astrid is rather unfavorable. He sees her being aggressive towards 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 both parties down but they still don't take too kindly to one another.
When Astrid takes off to tell on Hiccup and Toothless, they decide to kidnap her. Hiccup eventually manages to convince her to ride on Toothless with him, claiming that there is nothing to be afraid of. Toothless, however, has different intentions in mind. He leaps into the air and pulls off an array of dangerous aerial maneuvers until Astrid submits and apologizes. Toothless then smooths out the flight and gives Astrid 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 helps Hiccup try and keep Toothless concealed. Toothless later saves her from being eaten by the Red Death, and upon doing so, gives her a big toothless smile. At the end of the movie, Astrid is incredibly relieved to see that Toothless managed to save Hiccup.
In How to Train Your Dragon 2, Toothless greets Astrid and Stormfly with a big gummy smile which earns him an affectionate scratch from Astrid before he wanders off to play with Stormfly. During his first encounter with Eret, Astrid places a calming hand on Toothless as he snarls at the Dragon Trappers for capturing Stormfly. Astrid's relationship with Toothless is also shown to have a playful side, especially during dragon racing.
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Toothless and Astrid in "Race to the Edge"
Toothless seems to have a good grasp on Hiccup's feelings for Astrid, and he even teases him about it, most notably in the first movie and later on in Shell Shocked, Part 1. In Team Astrid he was particularly encouraging when Hiccup wanted to stay the night with Astrid at the academy. He was also seen worrying for her in Buffalord Soldier and was quite displeased when Viggo showed up.
He and Astrid also seem to share a common worry for Hiccup's well being, and understand one another's importance in his life. In Out of the Frying Pan, Toothless reacted to Astrid being in danger with immediate concern and straight away attempted to save her life by himself. In Blindsided, Astrid felt that Stormfly didn't want her and went to Toothless instead, and Toothless didn't seem to mind it in the least until Hiccup intervened, defending Stormfly's actions.
By the time of the second movie, it has been implied that Astrid knows how to fly Toothless in case of emergencies.
ValkaEdit
 "Oh, he's beautiful! Incredible! He might very well be the last of his kind. And look, he's your age! No wonder you get along so well!" 
 ―Valka during her 'inspection' of Toothless
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Toothless playing with Valka
Toothless is initially distrusting of Valka until she shows her ability to communicate with dragons like her son. He later becomes as docile around her as he does with Hiccup, most likely due to the family connection and her years worth of dragon taming experience. When they first meet, Toothless seems to enjoy Valka's company a great deal and tries to encourage her to come back to Berk so they can all be a big family.
Gobber the BelchEdit
Toothless and Gobber seems to be in friendly terms. In The Terrible Twos Gobber seems to understand Toothless and vise versa, but doesn't like Gobber's comments that involve Vikings before dragons.
Snotlout JorgensonEdit
Like Hiccup, Toothless shows some resentment towards Snotlout. In Defiant One, Toothless turned to Snotlout to help rescue Hiccup from the Outcasts. While the two did work well together, Toothless growled at Snotlout when he said he might not give him back to Hiccup. Toothless occasionally blasts Snotlout, usually when annoyed with him or helping him out when he's stuck. Knowing he needed a rider, he wasn't hesitant to put Snotlout on his back so he could rescue Hiccup from the lava of the Defender's volcano.
Fishlegs IngermanEdit
Toothless appears to be somewhat more gentle around Fishlegs than the other riders. When Hiccup got attached to Meatlug, who began attracting metal to her body, Toothless showed no hesitation to let Fishlegs ride him, and didn't do any "scary" maneuvers because he knew Fishlegs wouldn't be comfortable with them.
Ruffnut and Tuffnut ThorstonEdit
Like everybody else, Toothless is showed to be annoyed with the twins antics. The two rode Toothless when Hiccup and Barf & Belch were in trouble. Though Toothless was not thrilled by this.
HeatherEdit
Toothless was comfortable enough to let her ride him, along with Hiccup. While his reaction to Heather's betrayal was not seen, he seemed to have forgiven her, as he let her pet him goodbye. When Dagur offered Heather to join him, Toothless protected her from the Berserker chief.
Toothless was happy to see Heather and Windshear again in "To Heather or Not to Heather".
Dragon RelationshipsEdit
StormflyEdit
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Toothless and Stormfly say farewell during the Dragon migration
In the movies and franchise, Toothless and Stormfly share a very close friendship that rivals their riders'. They really seem to enjoy each other's company and can often be seen interacting on friendly terms. Sometimes Astrid's competitive nature can be seen in Stormfly, and that means that she and Toothless do occasionally get competitive.
On Race to the edge, they are usually seen chasing each other and playing in the background. Toothless' friendship with Stormfly is aided significantly by the fact that Stormfly's rider is Hiccup's closest human friend and girlfriend. As Hiccup and Astrid grow closer, so do their dragons.
When Toothless breaks free from the Alpha's control and calls other Dragons to aid him, Stormfly is the first dragon shown to return to herself and join Toothless' side as he makes his stand. After the Bewilderbeast's defeat, Stormfly acknowledges Toothless as the new Alpha Dragon by bowing down to him.
HookfangEdit
Toothless and Hookfang bare a completely different relationship to that of their riders. However at times Hookfang has seen to be pretty competitive with Toothless. They both share mutual respect for each other. 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. In How to Train Your Dragon 2, Hookfang acknowledged Toothless as the new Alpha Dragon by bowing down to him.
MeatlugEdit
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Toothless playing with Meatlug
Toothless have shown to be close friends with Meatlug as he shows to concern when she feels depressed as Fishlegs was neglecting her over wanting to win the competition against Snotlout. Meatlug also seems to care for Toothless as she was willing to help him out in the process of which Hiccup and Fishlegs were trying to cure Toothless from the eel effect. They often play with each other by rolling.("Living on the Edge") In How to Train Your Dragon 2, Meatlug acknowledged Toothless as the new Alpha Dragon by bowing down to him.
ThornadoEdit
Toothless did try to fight this wild dragon before Thornado got train by Stoick. Then they he later have good relationship with Thornado, and they learned to work together- in Live and Let Fly, they combined their shots to defeat Alvin's boat. Toothless understood that Thornado had to stay on Dragon Island to look over the babies Thunderdrum.
Barf and BelchEdit
Barf and Belch and Toothless are usually good with each other, although Toothless looked angry and annoyed when they crashed him and Hiccup from the sky in "The Zippleback Experience". Toothless usually will grab on their tails when they needed to be stopped if they cuase problems such as when they were not be with their owners as they went crazy when their owners were having fight and they were affected by the dragon root.It's unknown but HTTYD2 Barf and Belch acknowledged Toothless the new alpha by bowing to him.
Rival Whispering DeathEdit
 "So Toothless has an arch-enemy. Kind of like you and me." 
 ―Snotlout, to Hiccup[src]
Fight
Toothless fighting his rival
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. It is possible that they are no longer foes and consider the matter to be closed.
Toothless' experience with this dragon made him aggressive toward other Whispering Deaths though not too munch as seen with the Screaming Death Mother is a friend proving for Toothless there is some good in them.
TorchEdit
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From the moment Torch is discovered, Toothless instinctively didn't trust the youngling but knew the young Typhoomerang's mother was nearby and thus didn't want to risk angering her. Hiccup, however, ignored his warnings and took him to Berk anyway. From that moment, Torch began to irritate Toothless without mercy. He ate all of Toothless' fish, stole all of Hiccup's attention and took his bed allowing Toothless to become jealous of the attention the dragon got from Hiccup instead of him. Torch seems to be little brother that Toothless never wanted.
When the two meet again, they're still not on the best of terms, but are no longer as aggressive to one another.
The Screaming DeathEdit
Dragons Defenders of Berk Season 2 Episode 20 Cast Out, Part II Watch cartoons online, Watch anime online, English dub anime1377
Screaming Death confronting Hiccup and Toothless
Toothless met a new enemy: the Screaming Death. This large Dragon goes after him and Hiccup more than the other Dragons, most likely due to Toothless attacking the Screaming Death more often. Hiccup and Toothless were able to lure the albino Dragon into colliding with a sea stack, and injuring its wing. The Screaming Death obviously remembered this when they met again, as Hiccup and Toothless were its main targets other than sinking the islands. Toothless is happy to see the Screaming Death reunite with its mother. Though Toothless was bit surprised that the Screaming Death had forgotten who he and Hiccup were three years later, and they became rivals again.
FanghookEdit
Fanghook and Toothless
Toothless have shown to dislike Fanghook as he was wild dragon and roar at Fanghook when failing to shot accurate at the target when almost blasting the riders that were around. Later Toothless was shown to be bit thankful being saved by Fanghook from the trap.
Like other riders Toothless had shown to be very annoyed with Fanghook as he was standing on his back as Fanghook was being playful with him.
SkullcrusherEdit
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Toothless playing with Skullcrusher
Toothless was shown to dislike Skullcrusher at first because thinking it was very wild dragon that was attacking the Edge. Even though he went searching for this dragon seeming it was attacking his family, he was told by Hiccup to shoot at the Rumblehorn until Stoick stopped the attack, realizing that the wild dragon was trying to save everyone by making them flee from the edge before the huge tidal wave hit. When Toothless came on good terms with this new member of the family, they were sometimes seen running around together. In How to Train Your Dragon 2, Skullcrusher acknowledged Toothless as the new Alpha Dragon by bowing down to him.
CloudjumperEdit
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Unlike Toothless' playful personality, Cloudjumper is a more serious counterpart. The two appear to become friends after learning about the relationship between their riders and often observe the behaviors of each other during flights. Toothless even acts smug towards Cloudjumper when Hiccup reveals that he can fly on his own unlike Valka. Toothless attempts to get Cloudjumper to play with him multiple times, only able to get a reaction of the larger dragon when he has snow dumped on him. After becoming the Alpha after the Bewilderbeast's defeat, Cloudjumper is the first to bow down to Toothless, showing his respects. He seems to have a "caring older brother" attitude toward Toothless, and when he bows at the end before Toothless he does so with a hint of being proud of Toothless, almost in a fatherly way. in How to Train Your Dragon 2.
WindshearEdit
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Windshear appears to be comfortable around Toothless, as the two were seen nuzzling. When Toothless, Stormfly, and Windshear met up, the three were seen playing together. Toothless happily greeted Windshear when she and Heather returned to Dragon's Edge, but the Razorwhip growled at him, much to his surprise as she became bit like Heather trying to stay her distance from others. She did seem to settle down a bit later on, but she attacked Toothless again during a training flight. Once Windshear finally accepted the others, the two got along again. Toothless even regurgitated a fish for her, which she accepted.
ShattermasterEdit
In "Family on the Edge", Toothless have shown that he was helping this dragon to be trained by his new owner Dagur. Toothless even sees that Shattermaster was willing to give up his life to help his owner to defeat the Dragon Hunters.
SleutherEdit
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In "Stryke Out", Toothless was forced to fight a wild Triple Styke in the Dragon Fight Arena. As they fight it acurs to Toothless that he was fighting for his life. Toothless manages to get the upper hand during the fight, and as Toothless was going for the kill, he saw Sleuther's eyes close and it reminded him of his past, as Hiccup had done the same in sparing his life. As Toothless mangages to show the Triple Stryke there's no need to kill others for survival, Toothless manages to train of the wild dragon. He even flew next to Toothless thinking him a trustworthy friend, and mimics his grin, with tongue out and all.
Though by the time of "Blindsided", Sleuther has became a wild dragon on the Edge as he still has problems with humans. Even Toothless wasn't able to calm his friend as the Triple Stryke even tried to attack him. Though the results could be that his natural instincts came back after living in the wild with many dragons and he must hunt for food as he used to be fed in captivity for a long time.
Enemies, old and newEdit
Before meeting Hiccup, Toothless viewed all humans as enemies. It took some time before he opened up to others. Even after the events in the movie, Toothless still has some human enemies.
Current EnemiesEdit
Drago BludvistEdit
Toothless has a deep hatred for the self-proclaimed "Dragon God", especially after witnessing the atrocities of his trappers during the events of the second film. After Drago uses Toothless under the Bewilderbeast's control to attack Hiccup and ultimately kills Stoick instead, Toothless shows no mercy in throwing Drago to the ground when he is made free and ultimately fights back against the madman's Bewilderbeast.
Ryker GrimbornEdit
Toothless(93).jpg|thumb|260px]] Toothless dislikes Ryker and their fellow Dragon Hunters ever since he saw the dragon skeletons aboard The Reaper.
In "Midnight Scrum", when Ryker threatened Hiccup, Toothless almost killed him, but was stopped by Stoick.
Viggo GrimbornEdit
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Toothless hated Viggo since he first met him in Maces and Talons, Part 2. In "Last Auction Heroes", after Viggo almost sold Toothless at his auction, Toothless wanted to fight him instead of getting Berk's gold.
In "Shell Shocked, Part 2", When Viggo allied himself with the dragon riders in order to defeat his brother, Toothless didn't trust him. However, he let Viggo ride him. When Viggo ordered Toothless to stop, he just growled but obeyed when Hiccup told him the same.
Drago's BewilderbeastEdit
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.
Toothless might understand that this is the evil Bewilderbeast, raised to be evil for his owner who treated him harshly.
Former EnemiesEdit
Alvin the TreacherousEdit
Toothless doesn't hold back when facing the Outcast leader, almost threatening to kill him during a charger in the events of We Are Family, Part 2. In Cast Out, Part 2, Toothless is not thrilled about having Alvin join him and Hiccup to save Stoick, but did seem pleased as he and Hiccup watched Stoick and Alvin make up.
MildewEdit
Toothless shares a great dislike for Mildew. In How to Start a Dragon Academy, Toothless growls at the old man when he was making fun of Hiccup for thinking dragons could be trained. Though like Alvin, Toothless shows a bit more of a trust in Mildew after he is freed from Dagur's cage trap by him, showing that he begins to trust the old man.
Dagur the DerangedEdit
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Toothless shows more of his ferocious side whenever he sees Dagur, since he is obsessed with killing Dragons. Toothless began to slowly open up to Dagur in Enemy of My Enemy when the Berserker is trying to change. Like Hiccup, he did not trust him, but Dagur helped create a cure for the dragon root arrow Toothless had been shot with. He also allowed Dagur to operate his tail so the two could save Hiccup from the Dragon Hunters. He let Dagur ride him again for fun in Family on the Edge as proof that Toothless is believing that Dagur is becoming a better man, and was happy to have Dagur ride on him. Toothless was able to encourage Hiccup to trust Dagur since Toothless was learning to trust this former villain. 
Temporary RidersEdit
Astrid HoffersonEdit
In "Sandbusted", Astrid rode on Toothless to help Hiccup and Snotlout get away from a rogue Sandbuster.
Stoick the VastEdit
Stoick rode Toothless when the chief began his training. While Stoick enjoyed using Toothless for his chieftain responsibilities, the Night Fury did not. He even tried to hide from Stoick at one point.
Fishlegs IngermanEdit
Toothless let Fishlegs ride him when the two of them were trying to catch a magnetic Meatlug and Hiccup, who was attached to her.
Snotlout Jorgenson Edit
Snotlout rode Toothless when Hiccup was captured by the Outcasts, and attempted to ride him again after thinking that Hookfang has left him. Toothless then have Snotlout ride him in order to rescue Astrid and Throk who got trapped in the volcano of Caldera Cay, but the spewing lava proved too much for them.
Ruffnut and Tuffnut ThorstonEdit
When Hiccup was captured by the Dragon Hunters and Barf & Belch set out to rescue him, Ruffnut and Tuffnut rode Toothless to help them, much to the Night Fury's dismay.
Dagur the DerangedEdit
Dagur first tried to ride Toothless, but the Night Fury quickly bucked him off. Toothless finally let Dagur ride him so they could save Hiccup from the Hunters. Dagur rode him again to pass the time while Hiccup was getting a new leg, although he bucked him off when Dagur grabbed the base of his wing.
Drago BludvistEdit
When Toothless fell under the Bewilderbeast's control in How to Train Your Dragon 2, Drago used him as his method of transport to Berk. Once Toothless broke free, he threw Drago off his back.
From Book to FilmEdit
 "Setting Toothless up as a threatening presence gave us that vital sense of tension for Hiccup's story" 
 ―Chris Sanders, in The Art Of How To Train Your Dragon
Unlike his book incarnation, the film version of Toothless being a Night Fury is an original concept unique to the series. The Terrible Terrors were originally designed to be a more faithful take on Toothless' original incarnation, but as time went on in development, it was decided that Hiccup's dragon should have more presence and be able to stand toe-to-toe with his future tamer and lifelong friend rather than pairing the scrawny Viking with an equally scrawny Dragon:
TriviaEdit
 While Night Furies are nocturnal, Toothless is shown mostly active during the day, likely due to his relationship with the human characters and adapted to their schedules.
 Toothless' pupils change shape depending on his mood: when he is frightened, angry, or aggressive they narrow into thin, lizard-like slits, but when he is being friendly and happy they widen into round "puppy-dog" eyes.
 When Toothless is mind-controlled by the dark Bewilderbeast his pupils narrow thinner than ever before, giving him the appearance of a terrifying, mindless killer. As soon as he breaks free, his pupils widen bigger than ever before, when he shows fear, sadness and guilt over the death of Stoick and Hiccup's rejection of him.
 This is similar to another Dreamworks character, Puss in Boots from Shrek, whose pupils widen when he is trying to look 'cute'. 
 In Book of Dragons, Hiccup states that he has never seen another Night Fury besides Toothless. This could indicate that Toothless is the last of his kind, as Eret and Valka later guess in How To Train Your Dragon 2.
 The similarities of Toothless to Disney's Stitch (of Lilo and Stitch) are very prevalent and isn't just a coincidence: The creative team behind the film versions of How to Train Your Dragon (Chris Sanders and Dean DeBlois) are the same duo behind Lilo & Stitch.
 Toothless and Hiccup share many traits that makes them symbolically equal. The most prevalent of them are the fact they are both missing a left part of their body that is used for movement and that they are the same age.
 To further strengthen the connection, Hiccup's prosthetic leg operates Toothless' prosthetic fin, uniting both dragon and rider into a single cohesive unit.
 Ironically, Toothless lost his tail fin when Hiccup tried to kill him, but Hiccup lost his leg when Toothless tried to save him. 
 It is hinted that Toothless has a fear of lighting, ironic as Night Furies are referred to as the "unholy offspring of lightning and death itself."
 In some scenes from Riders and Defenders of Berk Toothless' color is dark blue.
 However, it is possible that this is made so Toothless can be seen in the night. 
 Toothless can sleep upside-down in a similar manner to a bat.
 Toothless is capable of walking on his hind legs, as shown during his attempts to draw like Hiccup and threatening to throw him off a cliff.
 In How To Train Your Dragon, if you look hard enough, it is shown that Toothless has markings on his body.
 When Toothless begins glowing for his climatic battle against Drago's Bewilderbeast, the way his spines light up with blue as he shoots unlimited fire blasts is a possible reference to the famous Japanese giant monster Godzilla, whose spines light up with energy as he unleashes his own atomic breath.
 Coincidentally, the American Godzilla film came out exactly one month before HTTYD 2. 
 Toothless seems to get the large scars on his legs from a battle with a Razorwhip, as shown in the episode 'Stryke Out'.