Toothless

The only known Night Fury in the story, and Hiccup’s best friend. He used to reside in the Dragon's Nest, but now lives on the Isle of Berk with Hiccup.

Role in the Franchise:
Toothless is known as the most feared, deadly, and mysterious dragon known to the Vikings, and as the only Night Fury in the Dragon’s Nest, Toothless was always the “dive bomber” during dragon raids. He was shot down by chance by Hiccup’s contraption “The Mutilator”, and his left tail fin was injured, being completely severed off.

Although Toothless could’ve killed Hiccup once he set him free, Toothless let him go, probably because Hiccup spared his own life. From then on, Hiccup and Toothless’s curiosity formed into a strong bond of friendship in which they have to be completely in sync to fly. 
The bond is strengthened in Gift of the Night Fury when Toothless willingly gives up his freedom of flight from the new tail Hiccup fashions, so he could keep his bond with Hiccup. In Riders of Berk, Toothless will get a new power as well.


In future installments of the franchise it'll be addressed at how Toothless is the only Night Fury anyone has seen--even though Hiccup thought there was an island of night furies in We are Family, part 1, it was just a trick via Alvin and Mildew. Toothless has always been a loner, but now that he has Hiccup, their bond is considered familial to Toothless because he has no one else. In Rider of Berk this is proved, since Toothless is the only dragon that is seen to constantly follow their rider around. Hiccup and Toothless spend mostly all their time together, even when simply doing leisurely activities. 

It is revealed in the episode What Flies Beneath that Toothless has a past enemy in a Whispering Death with an an unresolved grudge. It's never revealed what the two were fighting over, but whatever it was was it antagonized both Toothless and the Whispering Death to feel they needed a 'to the death' battle to settle matters. Toothless did eventually win the fight though did so without killing the Whispering Death. 


Personality:
Toothless is extremely intelligent and introverted in the beginning of the first movie. When he’s stuck in the cove, Toothless mostly fends for himself, not wanting to trust Hiccup much and only giving into Hiccup’s wanting to be friends when he realizes he needed Hiccup to fly again. Although Toothless was obviously annoyed with Hiccup’s trial and error tactics in getting his tail to work, once they finally learn to fly together Toothless’s playful side begins to show. This playful side is retained to mostly everyone in further installments to the franchise, unless Hiccup is threatened. 
In the event of Hiccup being threatened, Toothless becomes extremely protective of Hiccup, as shown in the first movie when he jumps into the Kill Ring to defend Hiccup against Hookfang as well as various moments in the tv series and seems to value their bond and friendship more than anything. Another fight between Toothless and Hookfang is seen in the episode Viking for Hire when Hookfang threatened Hiccup's well being yet again. In Gift of the Night Fury Toothless becomes very uneasy when Hiccup gives him a way to fly on his own, and when it came down to choosing, Toothless chose to fly with Hiccup’s assistance rather than having his own freedom. 

In The Terrible Twos Toothless is the only one who knows that Torch--a new baby typhoomerang found--is a baby and has a mother that's angrily looking for him. Despite everyone, even Hiccup, thinking that he's simply jealous Toothless still displays his protective side towards not only Hiccup, but the entire village, by trying to warn them about the angry mother before it's too late. 

Toothless also doesn't seem to be able to hold a long grudge towards Hiccup even if they're fighting as shown in The Terrible Twos, and despite Hiccup not believing Toothless, their friendship still remains intact.

Toothless is frequently shown to be frustrated with his prosthetic tail at certain moments in Gift of the Night Fury and The Terrible Twos similar to how Hiccup can become frustrated with his prosthetic.

Toothless is also, apparently, the more looked up to of the main group of dragons. In Alvin and the Outcasts Toothless was seen to settle a dispute between Hookfang, Barf and Belch, and was assigned the task to "take care of the other dragons" by Hiccup in In Dragons We Trust. 


Toothless has also seems to have a very humble attitude despite the constant blows at him in episodes such as Dragon Flower and When Lightning Strikes in particular. In When Lightning Strikes Toothless allows himself to be captured by the villages, knowing it would be bad for him to hurt them, as well as holding back his true powers even when facing enemies as to not kill anyone as seen when he is facing against Alvin. Nor does he ever seem to hold too much of a grudge towards anyone.

This all changed, though, in the episode What flies Beneath when Toothless is unexpectedly met with a rival from the past that he does carry a grudge towards. Toothless displays behavior in which he wanted to handle the fight himself and clean up his own mess on his own without the help of Hiccup. Snotlout identified with Toothless, saying that the fight was between Toothless and the Whispering Death and that he didn't want Hiccup around to help him in a fight that was his alone.

Toothless, multiple times, shoved Hiccup off in his attempts to mount him and help him out--for Toothless was loosing the battle because of his inability to fly on his own--but eventually his friendship with Hiccup overrode his pride and he let Hiccup help him after he had to save Hiccup from (intentionally) falling off a cliff.

Hiccup helped Toothless fly and win during the fight but urged him not to kill the Whispering Death, which Toothless didn't. It's assumed that even though the Whispering Death lived, the fight is over since Toothless still won the fight, yet spared him.

In We are Family, part 1 Hiccup tries to find other night furies for Toothless to be with, but Toothless never seemed too interested in finding them until the end when he thought he actually saw another night fury. Despite not having other dragons of his species to be with--and even Astrid claims this--Toothless seems to be extremely content with just hanging out with Hiccup all day, or the other dragons when not with him.

Abilities:

As a Night Fury, Toothless is able to shoot explosive arrays of fireballs and can fly at extremely fast rates, as well as the extremely rare ability to do a vertical take off. He can also retract both his top and bottom teeth into his gums when he doesn't feel threatened or when he's not eating.

In We are Family, part 1 Toothless revealed a new power--which he's, supposedly, never had to use up until that point--of being able to use echolocation when he and Hiccup were trapped in a cave in. 




Appearance:
Toothless is a black dragon, with yellow eyes and black, expressive pupils. He can retract his top and bottom teeth into his gums and has sharp nails on his front and hind legs. His wing span is perfectly proportional to his body type and—due to Hiccup downing him—Toothless his missing his left tail fin. Because of this fact, it’s hard for Toothless to fly longer than a few seconds on his own and he needs the assistance of rigged, prosthetic fin Hiccup fashioned for Toothless to fly. Although the first model of the fin needed Hiccup to operate it in order to fly, Hiccup did build a fin that Toothless can control on his own in Gift of the Night Fury, allowing him his freedom back. Toothless rejected this fin—wanting to fly with Hiccup instead—and whether or not Toothless will ever have to use this fin again is unknown.
Toothless also has many scars on his body, most of which coming from the bola sling that Hiccup shot at Toothless in the first movie. The most notable one is the scar on the right side of Toothless’s neck.

So far Toothless's tail as gotten four modifications. Two in How to Train Your Dragon, one in Gift of the Night Fury, and one in Riders of Berk (in episode 112).

Relationships:
Hiccup/Toothless (friendship)


Toothless/Whispering Death (rivalry)