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((AfC submission|t||ts=20230508072731|u=114.75.148.198|ns=118|demo=))<!-- Important, do not remove this line before article has been created. -->
((infobox fictional character
| series = [[How to Train Your Dragon]]
| image =
| alt = Toothless with the Light Fury in the [[How to Train Your Dragon: The Hidden World|Hidden World]]
| caption = Toothless with the Light Fury in the [[How to Train Your Dragon: The Hidden World|Hidden World]]
| name = Toothless
| first = [[How to Train Your Dragon (novel)|''How to Train Your Dragon'']] (2003)
| home = [[Isle of Berk]]
| lbl21 = Language
| data21 = Dragonese
| lbl22 = Owner
| data22 = [[Hiccup Horrendous Haddock III]]
| species = Night Fury
| lbl23 = Riders
| data23 = [[Hiccup Horrendous Haddock III]] (Most commonly)<br>Stoick the Vast (briefly)<br>Snotlout Jorgenson (briefly)<br>Fishlegs Ingerman (briefly)<br>
Dagur the Deranged (briefly)<br>Tuffnut Thorston (briefly)<br>Ruffnut Thorston (briefly)<br>Astrid Hofferson (briefly)<br>Drago Bludvist (Only in [[How To Train Your Dragon 2|HTTYD 2]])
| lbl24 = Status
| data24 = Alive (Most of the franchise)<br>Deceased (in [[DreamWorks Dragons: The Nine Realms|Dragons: The Nine Realms]])
))
'''Toothless''' is Hiccup Horrendous Haddock III's Night Fury and the main dragon character of the [[How to Train Your Dragon|''How to Train Your Dragon'' franchise]].<ref>((Cite web |title=Toothless - Dreamworks |url=https://www.dreamworks.com/how-to-train-your-dragon/explore/toothless |access-date=2024-03-09 |website=DreamWorks |language=en))</ref>

==Biography==
===''Training and Facing the Green Death''===
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's 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 cooperative 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 two 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. Toothless wrestles with himself, wanting to leave for survival but ultimately feels a sense of loyalty to Hiccup. He ends up saving him by making the Green Death sneeze, though the little Dragon got injured in the process when the Green Death swiped a claw at him. It is here where Toothless receives a scar above his heart, just as the dragons of the previous Hiccups have one. Hiccup plugs up the fire holes while inside the Green Death, leading to his explosion. A stray tooth flies through the air toward Hiccup, but Stoick saves him by throwing his shield in from of him. Stoick notices Toothless's wound and upon seeing himself bleeding, Toothless passes out.

Two days pass and Hiccup wakes up to find that Toothless has "died" from his wounds. Hiccup correctly guesses he is only in a sleep 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.

===''Hunting for the Treasure of G.G.''===
Toothless, as well as the other Hunting Dragons of the Hairy Hooligan Viking Novices go out on a boat for a 'Swordfighting at Sea', a part of the Pirate Training Program. Hiccup and Dogsbreath the Duhbrain spar with sheathed swords. However, Dosgbreath gets riled up beyond reason and tries to kill Hiccup. Toothless tried to intervene by biting Dogsbreath on the rear. Just as Dogsbreath is about to kill Hiccup, a mysterious coffin floating at sea rams into the ship, sinking it. All the boys, with the dragons flying make it back to Berk, along with the coffin.

Later, the coffin is determined to be that of Grimbeard the Ghastly, a famous historical Viking from whom Hiccup is descended. The Hooligans open the coffin and find a sickly and water-logged Alvin, the poor-but-honest-farmer. Alvin convinces Stoick and the Hooligans to go to the Isle of the Skullions to search for Grimbeard's treasure. The Viking Novices practice with their Hunting dragons, who are able to sniff out treasure. However, Toothless only manages to flush out three rabbits, and find an old spoon and a Turnip.

Likewise, on the Isle of the Skullions, Toothless is also unsuccessful at sniffing out treasure, and instead sniffs out a gigantic Limpet shell. Snotlout and Fireworm instead find the treasure chest. When the Hooligans open it, a booby-trap is released, and Toothless is one of the first dragons to smell it. The foul stench awakens the Skullions and the Hooligans desperately flee back to the shore and the ship. The hunting dragons simply fly to safety, however, Toothless attempts to be helpful and, along with Newtsbreath, awkwardly fly Hiccup back to the ship.

On the return trip to Berk, all the dragons except Toothless fly ahead home. Alvin cages Toothless aboard the Lucky Thirteen by placing a heavy barrel over him. This prevents him from raising the alarm when Alvin's Outcasts sneak aboard the ship and capture the Hooligans and the treasure. Toothless tries mightily to escape and finally tips the barrel over and rolls - still in the barrel - right into Alvin's legs, who was just about to kill Hiccup. The heroic Battle of Lucky Thirteen ensues, the Hooligans regaining their freedom. Ultimately the Hooligans won, but the black currant wine spills which turns out to be highly flammable. It catches fire and the Lucky Thirteen bursts into flames very rapidly and sinks. Most of the Hooligans and Outcasts get to safety on the Hammerhead, except Hiccup, Alvin, and Fishlegs. They sink beneath the waves along with the Lucky Thirteen, trapped in an air pocket within the upturned ship. Toothless joins them, though he is not at risk of drowning.

The air pocket rapidly dwindles. Hiccup sends out Toothless to see how far down they have sunken. According to Toothless, they are too deep to swim to the surface, but there is a cave with air closer by. Alvin complains that Toothless is taking a long time, and Fishlegs defends him. Using the last bit of air, Hiccup grabs Fishlegs and guides him, with Toothless leading the way. Alvin follows along as well. They resurface inside a cave deep below the sea's surface, but has breathable air and is even lit by luminescent Electricsquirms. Still in a near impossible predicament, Toothless puts his treasure-sniffing skill to use and finds a door with Grimbeard's writing on it, leading to another cavern. Alvin forces Hiccup to open the door, and it leads to a vast cavern full of treasure.

Alvin stops Hiccup and Fishlegs from leaving, and vows to kill Hiccup. They swordfight. Hiccup is at a disadvantage because his right arm is dislocated. He yells at Toothless to grab him a sword, since most of them in the cavern are much too large and ornate to be useful. Toothless grabs a small, plain sword as it is the only one he can carry. He gives it to Hiccup, who suddenly discovers that he is a left-handed sword fighter. Suddenly a Monstrous Strangulator rears out of the treasure and eats Alvin. It grabs Hiccup as well, but the boy tricks him into stabbing himself with his poisoned tail. Hiccup and Fishlegs leave the cavern with Toothless' help, since dragons can breathe out oxygen. The three return to the surface of the ocean and back to Berk, vowing never to talk about the hidden treasure.

===''Conflict with the Romans''===
As with the other Hunting Dragons, Toothless accompanied Hiccup on a 'Board-an-Enemy-Ship' lesson on the Sea-Known-As-Woden's-Bathtub. Hiccup, Fishlegs, and Toothless ride aboard The Hopeful Puffin, with instructions to board a Peaceable fishing boat and capture a Peaceable helmet. Snotlout and Dogsbreath - aboard the Sparrowhawk - ram into Hiccup's ship and send it spinning off course into the fog. Hiccup asks Toothless to keep an eye out for danger such as Sharkworms, but Toothless is defiant and refuses to do as told. He has an argument with Hiccup to which Hiccup must apologize.

Fishlegs, in a panic about Sharkworms, accidentally boards a Roman Ship in the fog and gets captured. Hiccup boards the ship to save him, leaving Toothless "on strike". After the boys encounter trouble while escaping and Hiccup yells, Toothless flies to his aid and attacks a centurion. The boys and Toothless escape, but at the last moment, the Thin Prefect throws a net and captures Toothless. The Romans toss him in a deep dark cell in a small cage with little to eat at Fort Sinister.

Hiccup and Fishlegs are also captured and taken to the fort, where Toothless is reunited with Hiccup. With the help of a Bog-Burglar named Camicazi, they try to escape numerous times, but fail. They are then forced to fight Sharkworms in an arena, where they escape with the help of Nanodragons. The children get into a Roman Observation Balloon while also getting rid of Alvin. The balloon ends up landing on the deck of Stoick's ship. The two tribes rejoice and return home.

===''Journey to Hysteria''===
Most dragons hibernate for the Winter, and Toothless is no exception. However, he did not dig a deep enough burrow and risks sleeping for hundreds of years from the chill. Hiccup dug him up, put a coat on him, and carried him inside his clothes. During a Hunting-With-Bows-and-Arrows-on-Skis outing with the Viking Novices, Snotlout happily whips the Sabre-Tooth Driver Dragons that pulled their sleigh. When Hiccup tells Snotlout to stop, he snaps the whip at Hiccup and hits Toothless on his scaly rear inside Hiccup's coat. He emerges angrily and then everyone laughs at him - including One Eye the Driver Dragon - because he's wearing a coat.

Later, Toothless goes with Hiccup on the 'Quest for the Frozen Potato', a mythical vegetable located on Hysteria. The Hysterics are having a huge feast in their Great Hall. Hiccup gets caught and is caged and hung from the ceiling. As the Hysterics fall asleep, Hiccup asks Toothless to get the key to the cage, but Toothless selfishly gorges himself first. Entirely too full, he trips on a utensil and ends up swallowing the key, as well as setting some rugs on fire. Eventually, the children and Toothless escape, encounter a Doomfang which steals the potato, and finds out that Hiccup has Vorpentitis who nearly dies. He is saved by Fishlegs.

===''Rise of the Exterminators''===
Toothless is with Hiccup and the rest of the young Vikings during a heat wave. He is a major part of keeping the Exterminators from conquering the Archipeligo. Hiccup sends him to drop the Fire-Stone into the volcano, which hatches into the Fire-Dragon that exterminates the Exterminators.

===''Saving Himself from Exile with His Friends''===
Toothless eats the Hooligans' stolen copy of How to Train Your Dragon by Professor Yobbish out of anger when Hiccup scolded him for not eating his spinach and driftwood.

===''To America''===
Toothless is with Hiccup, Fishlegs, and Camicazi during the Friendly Intertribal Swimming Race. He is also caught on the American Dream 2 with his master Hiccup.

===''The Darkness of Berserk''===
Toothless is with the rest of the Hairy Hooligans and the Bog-Burglars during their search for Camicazi. He accidentally swallows a spoon, which attaches to the the "magic stone" (which was most likely a magnet) he had eaten earlier. This gets suck in his stomach, among other things, and causes him to get sick. The items are removed later by Exellinor the Witch.

===''The Second Dragon War Begins''===
It is revealed that Toothless is actually one of the King's Lost Things, items to identify the new King of the Wilderwest. Hiccup picks up the rest over the course of the books. However, due to trickery and thievery, Alvin manages to steal the other nine things, leaving Toothless the only lost thing in Hiccup's possession.

===''Hunt for the Dragon Jewel''===
Toothless is the only Lost Thing Hiccup has left after Alvin the Treacherous confiscated the rest. Toothless also lived with Hiccup, the Windwalker, and the Wodensfang in the wild during the year between Book 9 and Book 10.

===''The Ten Companions of the Dragonmark''===
Toothless is a part of the Dragonmarkers, and doesn't trust Snotlout when he approaches them claiming to wish to Hiccup become king.

===''The New Kingdom of the Wilderwest''===
It is Toothless that brings back Hiccup's memories after he became amnesiac when hitting the mast of the boat he used to escape the Alvinsmen and their enslaved dragons. Toothless spoke to Hiccup and just from that his memories began to return in an instant, showing how strong their bond is.

==In other media==
=== Early life ===
Toothless lived in the Dragons' Nest on Dragon Island along with all the other dragons that would raid Berk and has hatched around 15 years before the events of the first film.

Sometime before the [[How to Train Your Dragon (2010 film)|first film]], Toothless encountered a Whispering Death, with whom he started a conflict. During one of their fight, the Night Fury injured the dragon by biting on its side, leaving a permanent scar. Even though the two dragons eventually parted ways, both of them held a grudge against each other for several years.

=== ''Meeting Hiccup and Ending the Dragon War'' ===
As the only known Night Fury, he remained elusive, and carried out strategic and lethal strikes against the Vikings' weaponry rather than steal food like the other dragons. He made sure that no Viking on the Isle of Berk ever spotted him. After Toothless destroyed several of Berk's catapult towers, Hiccup, needing some way to prove himself to the rest of the village, successfully shot the Night Fury down with his mangler cannon and sent him shrieking from the sky.

During the crash, Toothless lost his left tailfin, leaving him forever crippled from natural flight. The next day, Hiccup found him in the forest all tangled up and injured, as Hiccup prepared to kill the dragon, he was shocked to see how frightened the mighty creature was and instead spared him. Surprised that he was being set free, Toothless reared back, but instead of killing Hiccup, he simply pinned him to the ground and roared loudly at his face, before trying to fly out of sight. Toothless' sparing of Hiccup made him realize that the idea of dragons always going for the kill was wrong.

Despite having escaped from being killed, Toothless found himself trapped in a cove, unable to fly and therefore unable to escape. Knowing the dragon was still alive, Hiccup discovered the cove and observed him attempting to catch fish and his failed attempts at flying out. Toothless heard Hiccup drop his pencil and stared at him but remained passive. Hiccup later returned where Toothless was waiting on him. Though suspicious of the Viking, Toothless became relatively docile after Hiccup offered him some fish and removed his weapons.

The hungry dragon took the offer and regurgitated half of it into Hiccup's lap, deciding to "share" the piece of fish with him. Hiccup played along and faked a smile to hide his disgust. Curious about the mannerism, Toothless pulled his face into a confused and comical looking attempt at a smile. Hiccup was awestruck at the dragon's intelligence and reached out to try and touch him. Toothless was not interested and flew off to the other side of the cove, where he singed a small patch of grass and laid down. Hiccup attempted again to touch the creature, but Toothless didn't allow him to, choosing to sleep in a tree instead like a bat.

After waking from a nap, Toothless noticed Hiccup was still in the cove and curiously looked at the picture of himself that Hiccup was scratching out with a [[twig]]. Once again to Hiccup's utter astonishment, Toothless showed his intelligence by drawing a maze of squiggles and lines in an attempt to imitate the boy. Hiccup reached forward to touch the dragon again, but Toothless leaned back and growled. Hiccup then kept his hand open and closed his eyes in an act of trust, letting the dragon decide whether to close the gap or not. Amazed by the boy's bravery, Toothless leaned his head forward and touched his [[snout]] gently to Hiccup's hand for a few seconds, before flying off again.

Hiccup, knowing that Toothless was doomed unless he would be able to fly again, began to work on a [[Prosthesis|prosthetic]] tailfin for him. Their first attempt failed when Toothless realized that he needed Hiccup to operate it, after throwing him off. Over countless test flights, Hiccup designed tailfin after tailfin, each attempt bringing the boy and dragon closer. In between these flight tests, Hiccup discovered more of Toothless' playful and curious nature and applies his newfound knowledge to his advantage in Dragon Training.

Because of this, Hiccup became remarkably popular, much to the annoyance of his fellow Viking Astrid. Now extremely close friends through their interactions, Hiccup and Toothless carried out their first proper test flight. Though temporarily running into a snag, the two snapped into focus with one another and instinctively managed to carry out amazing mid-air maneuvers. The flight was a success and both Hiccup and Toothless were ecstatic.

Taking a break from flying, Toothless caught a small pile of fish and began eating it, while Hiccup rested at his side. A flock of Terrible Terrors came to them in an attempt to steal their food, so Toothless became protective of his fish. A Terror tried to drag away a fish from the pile, but the Night Fury quickly took it back and mocked the small dragon. As the Terrible Terror prepared to fire, Toothless sent a blast in its mouth, igniting the gas inside the creature. Dazed, the Terrible Terror walked away, but Hiccup offered him a fish, which the dragon ate happily. It approached the boy cautiously and went to sleep beside him.

After a couple of days, when Hiccup unknowingly led Astrid to the cove after she was bested in the final test. Toothless showed his protective side by assuming that she was a threat after hurting Hiccup. Only through Hiccup's words did he manage to calm down enough, though he was still wary of her. When Astrid threatened to tell the village of their friendship, Toothless abducted her and stranded her in a tree to stop her. Even though Hiccup invited her to a flight to show Toothless was not dangerous, the Night Fury wasn't convinced that Astrid could be trusted, and resented her for hurting Hiccup, pulling off daring moves to terrify her.

After she apologized, Toothless follows Hiccup's words and smoothed out his flight. He gave both Astrid and Hiccup a beautiful "dragon's eye view" of Berk and the beauty of the moment broke Astrid's long-held beliefs about dragons. Unfortunately, the Red Death chose this moment to send out a dragon call, and Toothless diverted their flight into a huge flock that was carrying great amounts of food. Hiccup and Astrid soon found themselves inside the Dragons' Nest, discovering that the monstrous Red Death effectively held the dragons hostage with its hauls and devoured the ones that didn't make satisfactory offerings. Toothless rocketed out of the mountain when the Red Death tried to eat him and the trio made a hasty retreat back to Berk.

The next day, Toothless heard Hiccup screaming from afar in the cove. Realizing that Hiccup must be in danger, Toothless managed to claw his way out of the canyon and immediately rushed to his human's side to protect him from the Monstrous Nightmare that Hiccup was supposed to kill in the arena in front of the entire village. He refused to leave his friend's side, even when the Vikings eventually got in on the fight and ganged up on him. He threatened to kill Hiccup's father Stoick, but only stopped when Hiccup yelled at him not to. This made the Night Fury let his guard down long enough to be captured. After learning from Hiccup that only a dragon can find the Nest, Stoick disowns Hiccup and has Toothless chained up and used him as a compass to find it.

Upon arriving at Dragon Island, the Vikings punched a hole in the nest using their [[Catapult|catapults]]. All the dragons from inside quickly fled the island, knowing what was coming. Toothless saw them from the [[boat]] he was on and realized with great fear of what was about to happen. Despite the Vikings' initial sense of victory, the Red Death suddenly burst out of the Nest and sets the entire fleet of ships on fire. Hiccup, along with the other teens on dragons of their own, arrived to save Toothless, but the Red Death broke the ship apart after stepping on it. Hiccup dove into the water in a desperate attempt to free Toothless but passed out from lack of air. To his shock, Stoick after saving Hiccup dove back into the water to break him free, and the Night Fury brought Stoick up to the surface with him. With a roar of encouragement, Stoick reconciles with Hiccup apologizing for everything, and Hiccup accepts his apology. Soom, Hiccup and Toothless teamed up to defeat the Red Death.<ref name=":1">((Cite book |last=Speregen |first=Devra Newberger |url=https://books.google.com/books?id=W9KIDQAAQBAJ&dq=%22Red+Death%22+How+To+Train+Your+Dragon+-wikipedia&pg=PP13 |title=DreamWorks How To Train Your Dragon |publisher=[[Random House Children's Books]] |year=2017 |isbn=9781524767754))</ref>

Toothless managed to aggravate the Red Death into chasing them even into the clouds, where the Red Death lost sight of them. Toothless shot several plasma blasts at it, to seemingly little effect. Enraged by plasma blasts bombarding its wings, the Red Death fills the entire cloud bank with flames, Toothless' prosthetic tailfin soon caught fire from the flames that the Red Death made, leaving them with little time to act. Toothless led the Red Death into a dive and waited until the larger dragon was about to breathe fire before firing one more plasma blast down its throat on Hiccup's signal. The Red Death slammed into the ground at full speed and caused a massive explosion that took its life.<ref name=":1" />

Though they tried to escape the flames racing after them, the loss of the prosthetic tailfin left Hiccup and Toothless unable to avoid a collision with the Red Death's clubbed tail, resulting in Hiccup getting knocked off Toothless' back. Seeing his human friend falling to his fiery death, Toothless bravely dove into the exploding body of the Red Death to save him. To Stoick and Astrid's relief, Toothless was able to save Hiccup's life by wrapping him in his wings, though was unable to save Hiccup's left leg from damage, permanently changing Hiccup's life.<ref name=":1" />

After returning home, Toothless was overjoyed when Hiccup woke from the battle. Sensing his human's shock at having lost part of his limb, he helped Hiccup walk with his new prosthetic, the pair of them now equally having lost a part of themselves. After Hiccup discovered Berk had taken the dragons in as companions, Toothless was given a new tailfin at the end of the film by Gobber and took off into the skies with his friend once again.

=== ''Putting out a Fire'' ===
When Gobber's home caught on fire due to a pair of pants left on the stove, Toothless and Hiccup helped in putting it out. Toothless then landed near Stoick, worrying about Gobber's safety, along with Hiccup. The old man blamed a Boneknapper for what happened and left to search for the dragon. Hiccup decided to accompany him along with the other teens. They started the journey the next day, leaving their dragons on Berk, including Toothless.

=== ''Welcoming a New Trainer'' ===
While Hiccup, Astrid, Fishlegs, and Gobber were updating the Dragon Manual in the Great Hall, Toothless playfully entered the building and jumped around his rider. When Hiccup asked the dragon what was going on, the Night Fury enthusiastically pointed his snout towards the camera, showing everyone the new dragon trainer. The teens and Gobber then briefly describe several dragon species and the origins of the Dragon Manual to the trainer. After they finish, Hiccup stated that he doesn't know the maximum speed of a Night Fury. Toothless then became agitated, understanding what his rider said. The teens then left along with Toothless, wanting to find out the answer.

=== ''First Snoggletog with Hiccup'' ===
As preparations for Snoggletog begin in Berk, Toothless wakes Hiccup up by jumping on his roof. The two of them go out for a flight, and try out a new move, but Hiccup loses his helmet. The pair return home where they are bombarded with the news that the island's dragons have all left. Toothless appears to want to follow, making Hiccup feel guilty about the fact that Toothless can't fly on his own. So he ends up building a special prosthetic for Toothless that allows him to fly independently. But after giving the new prosthetic tailfin to his dragon, Toothless leaves just as quickly as the other dragons.

Hiccup, upset that Toothless has seemingly abandoned him, later discovers that the other dragons have left Berk to have their babies. Though he is unable to see Toothless on the island they have gone to, he brings the dragons back home as Berk celebrates Snoggletog at last. He questions where Toothless may have gone until the Night Fury returns, attempting to sneak into the hall without being noticed. He is quickly spotted and runs up to his human happily, revealing a drool covered helmet as a gift. Realizing that Toothless had left to try and find his lost helmet this whole time, Hiccup hugs his dragon in thanks.

The next day after waking Hiccup up, Toothless has dragged out the old tailfin and saddle in anticipation of their flight. Despite Hiccup's protests to stop goofing around as he has his new automatic tail, Toothless proceeds to smash it into the ground and fling it away. He nudges the saddle towards Hiccup, leaving his friend in awe that the dragon would rather fly with him or not at all. As the pair take off and perform a daring freefall, Hiccup remarks how while he may have given his best friend independence, Toothless gave him the better gift of his companionship.

=== ''Adapting to Berk Society and War with the Outcasts'' ===
Toothless practically never leaves Hiccup's side during the events of the TV series. It is revealed they now sleep in the same room where Toothless has his own bed made from a slab of stone raised off the floor so he can safely heat it with his flame.

In "How to Start a Dragon Academy", the dragons on Berk run rampant, causing Hiccup and Toothless to try and maintain the peace they worked so hard to forge. After one too many incidents, one involving Toothless himself, Stoick, at Mildew's urging, decreed that the dragons would be banished once again. Hiccup and Toothless manage to find a way to use the dragons' abilities to aid the Vikings with fishing and farming. Stoick reverses his decision and gives the responsibility for the dragons to Hiccup and his friends. The Berk Dragon Training Academy has officially started to train them.

In "Viking for Hire", Toothless supports Hiccup in his attempts to help Gobber find a new place within the new Viking and dragon community as there was no longer any need for dragon killing weapons. When Hookfang goes on a rampage due to a toothache, the two dragons have a brief scuffle until Gobber managed to discover the cause of Hookfang's behavior and removes the tooth.

During the events of "Animal House", Toothless' protective instincts still show themselves fiercely whenever Hiccup gets into danger, managing to save him from an avalanche and help gain the trust of the surrounding animals.

In "The Terrible Twos", however, this loyalty also shows a jealous streak, as seen when Hiccup discovers a young Typhoomerang named Torch. Jealous of the attention Hiccup gives Torch, and afraid of the baby dragon's parents, Toothless finds that his mother is enraged with worry and looking for him. Attempting to take Torch to her directly, Hiccup becomes frustrated with Toothless' behavior and leaves him in The Cove as punishment. After Hiccup and the other riders realize what is going on, Hiccup quickly finds and apologizes to Toothless before luring the mother away and returning Torch to her.

As shown in "In Dragons We Trust", after several disasters occurred in the village seemingly caused by dragons, Toothless is blamed for the destruction of the armory. At the villagers' demands, Stoick once again banishes the dragons from Berk, much to Mildew's joy. The riders take their dragons to Dragon Island and are forced to leave them there after several sad farewells. Hiccup vows to be back for Toothless. Toothless waits on the Island for Hiccup to return and keeps the peace between the other dragons in the meantime.

During the events of "Alvin and the Outcasts", eventually, Hiccup does return but as a prisoner of Alvin the Treacherous, who has invaded Berk to capture the 'Dragon Conqueror'. Together, the dragons and Riders manage to destroy the Outcast ship and return to Berk, once more welcome there despite Mildew's protests.

As shown in "How to Pick Your Dragon", Hiccup manages to convince Stoick to start dragon-riding. Stoick quickly decides that only a Night Fury is worthy of a Chief and rides Toothless for an entire day, causing him to become exhausted and lonely without Hiccup. Not wanting a repeat the next day but yet respecting Stoick enough to be unable to directly refuse the chief, Toothless hides from Stoick instead. After several disastrous attempts by the other riders to convince Stoick of their dragons' advantages, Toothless is forced to chase down a rogue Dragon, revealed to be a Thunderdrum. Toothless tracks it down and helps the Thunderdrum's friend. Stoick bonds with it during an attack by boars and everyone returns safely back to Berk.

During the events of "Portrait of Hiccup as a Buff Man", Toothless and the other Dragons carried their riders around the island to assist in Hiccup's quest for the treasure of Hamish I. He burned through the glacier to get the first key, but was unable to fly to get the second one due to high wind conditions. He was the only one who accompanied Hiccup to the final resting place of the treasure as the others had been cut off from them by a cave-in.

As shown in "Dragon Flower", Toothless spends most of his time sick after being been poisoned by the Blue Oleander, along with every other dragon on Berk. Hiccup, Stoick, Gobber, and an unwilling Mildew are forced to track down and extract venom from a Scauldron to use as an antidote.

During the events of "Heather Report, Parts One and Two", Toothless and Hiccup encounter the survivor of a wrecked ship, a girl named Heather. While curious about the newcomer, Toothless doesn't see her as a threat and even lets her ride him with Hiccup. When Heather steals both the Book of Dragons and Stormfly, Toothless uses his speed to catch up. Despite trying to get the Book back, Hiccup is subsequently burned by flaming catapults and Toothless retreats, leaving the Book on Outcast Island.

As the dragons and riders eventually reclaim the Book and realize that Heather was only working for the Outcasts because they had captured her parents, they clear things up with her and Toothless lets her pet him before she leaves.

In "Thawfest", during the Thawfest Games, Toothless' competitive side was shown. At first he felt bad for Hiccup, who wasn't doing too well on the first day. On day two, like Hiccup, he let his competitive nature get the best of him. He was just as determined to beat Snotlout and Hookfang as his rider. However, Toothless seemed to understand that Hiccup threw the race and was fine with coming in second.

In "When Lightning Strikes", Mildew tries to convince the Vikings that Toothless' status as a Night Fury was angering Thor and causing various lightning storms to strike the island. It is later revealed to be the metal dragon perches and the statue of Thor that attract the lightning.

As shown in "What Flies Beneath", when holes were found on Berk, it was the only occasion where Toothless has defied Hiccup. A Whispering Death that Toothless had fought in the past comes 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, he eventually accepts Hiccup's aid when Hiccup deliberately jumps off a cliff to force his dragon to choose between his human or his long-standing vendetta.

During the events of "Twinsanity", Hiccup then attempts to teach Toothless hand signals. While he is fine with "battle-ready" and "plasma blast," he remains a little confused with "smile" and "search". However, he was able to fool Dagur the Deranged and his Berserkers during their fake dragon attack.

In "Breakneck Bog", After the riders are looked for Hiccup's lost gift and heard the story behind the dragon doll, Toothless looked touched by the tale, understanding its importance. Toothless then encourages Hiccup that the two go for a night flight.

As shown in "Gem of a Different Color", Toothless helped defend the village from the Changewings who were searching for their eggs.

During the events of "We Are Family, Parts One and Two", During Bork Week, Toothless and Hiccup then journey off, looking for more Night Furies. Though Toothless seems only slightly interested at first, they become excited as they come closer and closer to their goal. Unfortunately, the prospect of other Night Furies turns out to be is a trap set by Alvin and Mildew.

Toothless is locked into a high-security cell in the Outcast Dragon containment area. Toothless proves his intelligence when he escapes on his own. He fools the Outcasts into thinking that he is sick and immediately blasts them back when they get close. Notably more violent than he usually is with humans, Toothless' primary concern is finding Hiccup who is missing. They eventually find each other using dragon calls and decide to attack Alvin for what he has done. Both boy and dragon usually refrain from going for the kill but feel that Alvin has gone too far and dive for him.

It is yet another trap, and they are both temporarily captured by bolas until 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 to the horizon, confident that they will be there for each other in the battles that are yet to come.

=== ''Outcast War Continues and the Berserker War'' ===
Months later in "Live and Let Fly", Toothless initially acts very grumpy after Stoick issues a ban on flight. He starts to grate on Hiccup's nerves, trying to convince him to go on their nightly flight and only succeeds in doing so when Gobber talks to Hiccup. He and Hiccup start a "Dragon Flight Club" to train the other Riders in secret. Later, he and Thornado combine forces in driving off an attack by Alvin and the other Outcasts.

During the events of "The Iron Gronckle", Toothless blasts an arrow flying at Meatlug who became magnetic.

As shown in "The Night and the Fury", Toothless and the other dragons endure Tuffnut's 'scary' stories while Hiccup and the others are on a training mission. Waiting until Tuffnut falls asleep, they sneak out to find their riders. He is spotted by Dagur who is on Dragon Island with the sole purpose of killing the Night Fury and is hunted by him and, unwillingly, Hiccup across the entire island. When Hiccup decides to end his charade with Dagur, he uses his Dragon Call to call Toothless. Though caught in Dagur's bolas when they try to fly away, Toothless helps Hiccup battle Dagur after initially being forced to watch his human fight on his own.

In "Tunnel Vision", Toothless then meets a dragon who would later become one of his greatest enemies, the Screaming Death. After he and Hiccup escape several Whispering Deaths in their underground tunnel network and drove them out of Berk, he was quickly forced to engage with the Screaming Death who knocks him out of the sky. Thanks to Hiccup's shield and Toothless' speed, along with the Screaming Death's attraction to sunlight, they were able to use the Screaming Death's size against it and force it to crash into a giant sea stack, injuring its wings.

During the events of 'Race to Fireworm Island", Toothless was pitted against Stormfly in a training exercise and was able to evade her by flying into a cave and blending into the darkness, along with Hiccup. Later, when Hookfang fell gravely ill, he helped Hiccup gather Fireworms and saved Snotlout from the Fireworm Queen when Snotlout stole a fire-comb from her nest.

As shown in "Fright of Passage", Hiccup and Toothless helped Astrid to sneak up on the Flightmare as only a Night Fury had the stealth at night required to do so. He defended both of them from the Flightmare when it believed its food source to be under attack but as they discovered this, Toothless ate some of its algae, causing him to glow purple. Later, when Fishlegs, Meatlug, and Stormfly appeared to help, he cut a new channel for the river to divert the flow of algae out to the sea, forcing the Flightmare off Berk.

In "Worst in Show", Toothless learned a rescue skill that gave him a new way to use his plasma blasts by firing multiple shots as he barrel-rolled. He tried to comfort Meatlug when Fishlegs neglected her, in favor of training his Terrible Terror, Iggy, so he could beat Snotlout in a training competition. Toothless assisted Hiccup in demonstrating Sharpshot's accuracy and, later, used his new rescue skill to destroy Alvin's ship.

In "Appetite for Destruction", Toothless carried Hiccup to several islands that had been mysteriously sunk. It was later revealed that the Screaming Death had returned. It attempted to destroy Dragon Island and was revealed to be behind the destruction of other islands in the area. Toothless and Hiccup managed to hold out long enough for Fishlegs and Astrid to gather as many wild dragons as they could to fight off the Screaming Death.

As shown in "Zippleback Down", Toothless ventured around Berk, disabling old dragon traps left over from the war until Hiccup noticed the hot wind and lack of rain, indicating they were having fire weather. He also helped Hiccup track down the twins, who were trapped in a forest fire and was reunited with Torch, who Toothless was less than thrilled to see again. Toothless and Torch, along with Barf and Belch, were able to use their fire, wings and Torch's abilities to put out the fire.

During the events of "A View to a Skrill, Parts One and Two", Toothless and Hiccup then discovered a frozen Skrill near Berk and hurry to get it off the island, knowing how it is revered by the Berserkers. When the mighty dragon is thawed out, the pair of them face the prospect of a war between the Skrill, Berserkers and Alvin's Outcasts who manage to take the dragon for themselves.

It is later revealed that the Outcasts and Berserkers intend to form a truce between themselves, using the Skrill as their weapon of choice to invade Berk. Though the two groups eventually fall out with each other, Toothless and Hiccup manage to seal the Skrill back into its icy prison and avoid a potentially deadly battle.

As shown in "The Flight Stuff", Toothless carried Hiccup on scouting runs to Outcast Island so that they could see what Dagur was up to but during one of these scouting missions, Hiccup and Toothless were captured and nearly killed, due to Gustav and Fanghook's interference and eagerness to help. However, Snotlout and Gustav managed to use their Dragons to free them while Astrid and Stormfly distracted the other Outcasts.

During the events of "Free Scauldy", Toothless and Hiccup, along with the other members of the Dragon Flight Club, started searching for the Screaming Death as they decided it was too dangerous to leave unchecked. When they passed Changewing Island, they discovered an injured Scauldron, which rebuked all their attempts to help it, even though it would have died if left out of the water too long. Toothless, Meatlug, Barf and Belch refused to leave it and, eventually, they were able to help it by lifting the rocks off of its wing when it took a liking to Ruffnut. They managed to fix the Scauldron's wing with a large makeshift splint, which Ruffnut cut off her braids to finish.

In "Frozen", after being stuck inside a shelter, due to a massive snowstorm, Hiccup and Toothless went on a Search and Rescue mission for Trader Johann. Toothless used his Echolocation to great effect across the frozen sea but, shortly after they left Berk, they almost collided with the Speed Stinger Horde. After finding Johann during the night, they returned to Berk during the day to find the village mysteriously empty. He searched for the Speed Stinger nest, along with the other Dragons and their riders, so that they could capture the Alpha and use it to lure the Horde away from Berk. Toothless engaged the Alpha in one-on-one combat and, with Stormfly's help, managed to force it into a cage. Later, he carried it across the sea after Stormfly got stung carrying it and got paralyzed, luring the horde away from Berk. Afterwards, they flew Johann back to his ship so he could continue trading.

As shown in 'A Tale of Two Dragons", Toothless spent most of his time with Hiccup, helping to sort out Mildew's old cabbage field and trying to break up Stormfly and Hookfang when they were fighting each other, only for Toothless to start fighting too. Eventually, they discovered the cause of the aggression was Dragon Root, which Meatlug was immune to, and threw it into the ocean.

In "The Eel Effect", Toothless eats an eel by mistake while trying to save Hiccup and becomes very sick, attacking Hiccup and shooting his fire randomly everywhere. When Toothless sees that he has hurt Hiccup through his sickness, he runs off. When Hiccup and Fishlegs find Toothless, a huge blue Typhoomerang attacks and events eventually lead Toothless to run off a cliff edge out of control. Hiccup quickly puts his foot into the stirrup and tries to control Toothless, the dragon refusing to let him on. Hiccup and Fishlegs manage to ensnare Toothless long enough to give him the medicine for the eel. He regurgitates the eel and returns to normal.

During the events of "Smoke Gets in Your Eyes", Toothless then sensed that something was very wrong with the pile of scrap metal that Gobber bought from Trader Johann but, nevertheless, helped get it to Gobber's forge at the blacksmith request. The next day, he and his rider woke up to find out that the entire village had been robbed of plenty of metal objects and they both, along with Astrid and Stormfly, investigated the scenes of the crimes, to no result.

Later, in the night, Hiccup was attacked by adolescent Smothering Smokebreaths, who were attracted to his metal leg and Toothless helped to fight them off, before going to tell the others. After setting a trap, they followed the Dragons to their nest, only to find out that the entire situation had been orchestrated by Dagur, who was on the horizon with his armada. To end this threat, Toothless carried all the metal the village had left, along with the other Dragons, and threw it at the Armada so that the Smokebreaths would steal all the components from Dagur's ships causing them to sink. He then helped lure the Dragons to Johann's boat, who was making a stop at Breakneck Bog.

In "Bing! Bam! Boom!", Toothless and Hiccup, along with Stoick and Thornado, discovered three baby Thunderdrums out at sea and, unknowingly, led them back to Berk, where they started causing havoc and disaster. Toothless and the other members of the Academy tried to train the three Dragons but it turned out that only Thornado could control them and so Toothless and Hiccup, as well as Fishlegs and Stoick, left them on Dragon Island after several failed attempts. They found out that the other Dragons on the island had chased them out to sea in the first place and so Toothless, Meatlug and Thornado fought off several Dragons of different species to defend the hatchlings. Afterward, Toothless carried Hiccup and Stoick back to Berk since Stoick had left Thornado behind to look after the hatchlings.

During the events of "Cast Out, Parts One and Two", Toothless and Hiccup saved Astrid when she fell off of Stormfly. Alvin later rode on Toothless along with Hiccup on the way to Outcast Island.

=== ''First Dragon Race with Hiccup'' ===
During the short that explains the formation of Dragon Racing, it is revealed that Toothless' preferred color for the event is red, matching his and Hiccup's attire. Toothless was part of the first Dragon Races, finding sheep in places where other dragons couldn't, and coming very close to winning on his own.

=== ''Discovering the Dragon Eye and the Founding of the Edge'' ===
During the events of "Dragon Eye of the Beholder, Parts 1 and 2", three years have passed since the war with the Berserkers. Toothless and Hiccup fly out in the hope of searching for new lands and dragons but to no avail. After Johann was fished from the ocean, Toothless went with his rider and the other riders to the Ship Graveyard in an attempt to capture Dagur. Once there, Toothless went with Hiccup to take a look at The Reaper, where they found the Dragon Eye. They were then confronted by Dagur and his Berserkers.

After Hiccup gave up the Dragon Eye to Dagur in exchange for being allowed to save his friends, Toothless then tried to blast the cage open, but to no avail. Despite this setback, Hiccup's friends were saved and Toothless was able to retrieve the Dragon Eye from Dagur. Toothless then went with Hiccup, Gothi and the other riders to Glacier Island. There they fought the Snow Wraith in order to get one of it's teeth to unlock the Dragon Eye. After they returned to Berk, Toothless was able to use his fire to light the Dragon Eye.

As shown in "Imperfect Harmony", Toothless was present when Hiccup showed the Dragon Eye to Stoick and the other members of the Berk Council . After giving his son permission to leave Berk, Stoick entrusted Toothless to take care of Hiccup, which the Night Fury grunts in agreement. They soon reached a beautiful island where the Riders stop to rest. The next morning, however, the dragons were gone. Toothless later found Hiccup and the others, telling them the other dragons were in danger.

In a rush, Toothless grabbed Hiccup's metal leg and accidentally yanked in off without even knowing. Once realizing that he had only the prosthetic, he returns it to his rider, with a guilty look. After chasing off a wild Thunderdrum, the Riders encounter a new dragon, the Death Song, and learn that it draws in dragon with its song, then traps them in its amber blasts to eat them later. While the Riders were trying free their dragons, Toothless faced the Death Song, only to get caught, as well as everyone except Hiccup. Using the Monstrous Nightmare gel Snotlout brought, as well as the aid of the Thunderdrum from before, Hiccup freed everyone and trapped the Death Song in a cave.

In "When Darkness Falls", the Dragon Riders finally found an island to use as their outpost. Like Hiccup, Toothless was not fond of the other Riders arguing over designs for their base. When the duo, along with the twins, discovered the Night Terrors and captured their leader, they returned to the others. They soon realized the small dragons are defenseless without their Alpha's guidance. Toothless and Hiccup return the leader, which Tuffnut named Smidvarg to his pack and chase off the Changewings that were threatening them. After finally deciding a design for Dragon's Edge, the Night Terrors become the island's sentries. Smidvarg gathers the pack together to form a giant Night Fury as a sign of their alliance, much to Toothless' enjoyment.

During the events of "Big Man on Berk", Toothless and the other dragons then attempted to relocate a wild Scauldron from Berk's fishing lanes. However, they had difficulties due to Fishlegs' allergy. They also had problems when Fishlegs turned into his alter ego, Thor Bonecrusher, and attempted to tame the Scauldron multiple times. When Fishlegs turned back into his normal self, Toothless and Hiccup had to save both him and Meatlug from the Scauldron.

In "Gone Gustav Gone", after Gustav Larson and Fanghook came to visit Dragon's Edge, Toothless showed completely annoyance towards the boy and his dragon. Later, when Gustav took the Dragon Eye without permission and went to an island hoping to find a treasure, Hiccup and Toothless had to rescue him and Fanghook. The next day, after Gustav disappeared, Hiccup received a message saying Dagur had captured him. Hiccup and Toothless then go to rescue the boy, but Gustav pretends to be on Dagur's side. Hiccup and Toothless left without him, but instead of returning to the Edge, they went to the island where they rescued Gustav earlier and hid in the caves. There, they ambushed Dagur and rescued Gustav. They also found a Dragon Eye lens in the process. They then returned to Dragon's Edge, where Hiccup shared the news with the other riders.

In "Reign of Fireworms", when Ruffnut and Tuffnut were made the rulers of Dragon's Edge after the discovery of The Twins' Namey Rock, Toothless is annoyed by the idea, along with the other riders. He even growls furiously at Tuffnut when the latter gives Hiccup the job of a stable boy. Toothless later helps Hiccup wash Barf and Belch by boiling a bucket of water in front of the twins, causing the ash to stick to their faces. Tuffnut then tells Toothless that be will be keeping an eye on the dragon. Hiccup and Toothless are later "imprisoned" by the twins, after breaking a rule by flying in front of them. While locked in the stables, a big flock of Fireworms arrives on Dragon's Edge, threatening to burn everything. The twins then release Hiccup and Toothless to find a solution for the incoming dragons. With the help of the Night Terror flock, which took the shape of a Fireworm Queen, Hiccup and Toothless managed to relocate the small dragons to a nearby island, from which they could continue migrating.

As shown in "Crushing It", Toothless then assisted the rider in their attempt to capture a wild destructive Rumblehorn. However, with Stoick's help, Toothless realized that the Rumblehorn was trying to warn them of a tidal wave coming towards the edge.

In "Quake, Rattle and Roll", Toothless then went with Hiccup, Fishlegs and Meatlug to Dark Deep. However, once there they saw that the Gronckles had been pushed off by a Catastrophic Quaken. Toothless was unable to force it to leave but then watched as Meatlug and Fishlegs made friends with it and the Gronckles.

During the events of "Have Dragon Will Travel, Parts One and Two", Toothless then helped the riders track down a rogue dragon and it's rider. Toothless was able to shoot the dragon and its rider, who revealed herself to be Heather. Toothless was then able to follow Heather to Trader Johann's Ship, where he and Hiccup forced Johann to give him information on Heather's next target; Dagur.

Toothless then saved Heather and Windshear from Dagur's chains and escaped, back to the Edge. There, Toothless told the other dragons to back off from Windshear. Toothless then helped Hiccup convince Heather to not kill Dagur because he was her brother.

As shown in "The Next Big Sting", Toothless then watched Hiccup tested his prototype Flightsuit. He saved Hiccup from crashing in the first two tests. Toothless, along with a Speed Stinger, Speedy, were able to force his pack to leave the Edge.

In "Total Nightmare", Toothless then assisted Hookfang and Snotlout in defending Girl Hookfang's eggs from Titan Wing Monstrous Nightmare.

=== ''War with the Dragon Hunters'' ===
During the events of "Team Astrid", Toothless and Hiccup then searched for Dagur after he attacked Berk. However, he and the other dragon and their riders came under attack at the Edge by Dagur's fleet. However, they received help from Astrid, Stoick and the Dragon Riders' Auxiliary.

As shown in "Night of the Hunters, Parts One and Two", Toothless and Hiccup then saved Astrid from drowning following Stormfly's kidnapping by the Dragon Hunters under Ryker Grimborn. However, they were defeated and had to retreat. Later, Hiccup came with the idea of using Screaming Death scales as armor for Toothless and Hookfang, protecting them from the Dragon Root Arrows. The plan worked and they saved all the riders.

In "Bad Moon Rising", Toothless, Hiccup, Fishlegs and Meatlug go to Lycanwing Island in search for the mythical Lycanwing dragon. However, they found out that the Lycanwing was only an invention to keep humans away from a Dragon Eye Lens. Also, when Tuffnut fell off a cliff, Toothless was the one who caught him.

=== ''Alliance with Dagur'' ===
In "Enemy of My Enemy," Toothless gets shot down with a dragon root arrow. He lands on Nameless Island, and he and Hiccup are found by Dagur. Dagur, who has become a much better person after a long period of isolation, helps Hiccup make the cure for dragon root. However, Hiccup is captured by the Dragon Hunters. Toothless, once cured, allows Dagur to ride him to save Hiccup.

=== ''Defeating the Dragon Hunters'' ===
In "Shell Shocked, Part 2," Hiccup and Toothless finally destroy the last of the Dragon Hunter ships and Project Shellfire. Ryker Grimborn is killed, Viggo is thought to be killed, and the Dragon Hunters were hopefully neutralized forever.

=== ''War with the Dragon Flyers'' ===
In "Dawn of Destruction," Krogan the Dragon Hunter has Flyers riding Singetails attack the Edge. As Hiccup and Toothless are away, Krogan is able to take the Edge with only a few casualties. Over the rest of the season, the Dragon Flyers continue to attack the Riders and capture dragons, along with the Dragon Hunters that were thought to be defeated and Viggo Grimborn, who had survived. Hiccup and Toothless manage to defeat them every time it comes to direct combat, but the Flyers continue to grow stronger and continue to hunt and kill dragons.

=== ''Aiding the People of Nepenthe'' ===
When a rampaging Thunderclaw runs through the village with Snotlout on its back, Hiccup and Toothless attempts to calm him down. However, they only manage to get Snotlout off, as the Thunderclaw continues to run towards some children. Hiccup and Toothless then separate and the Night Fury turns into his Alpha mode, finally stopping the Thunderclaw. Toothless then plays with the children Hiccup saved.

Toothless then watches how Hiccup argues with some villagers about Eret and becomes angry when they try to attack his owner.

Later, in the Great Hall, Toothless plays with Cloudjumper while Valka talks to Hiccup. Toothless then watches as Hiccup speaks with Calder, an emissary from Nepenthe who is seeking help.

On their way to Nepenthe, the riders are accompanied by Tidal Class dragons which bring Toothless fish as a sign of respect for their new Alpha. He is very happy about this, as he eats fish from a Scauldrons mouth, then flies graciously above some Thunderdrums.

On Nepenthe, Toothless accompanies Hiccup as they meet Mik, the king of the island. Toothless then relaxes in one of the many hot pools of the island, despite Hiccup wanting him focused on the task.

At dinner, Toothless, along the other dragons feast on the various food, but they all quickly collapse. Calder then appears and captures all the dragons and riders.

After Hiccup escapes, he brings Toothless in his Alpha mode, along with the other dragons and the riders prepare to leave the island. However, right then, some Foreverwings wake up and began destroying the village. Hiccup and Toothless attempt to calm them down and succeed after Toothless turns into his Alpha mode. He presumably tells the dragons to leave the island. He and Hiccup are then attacked by Calder who is using Hiccup's Inferno. While Toothless growls in the background, Hiccup throws a canister of Zippleback gas at Calder, killing him.

The next day, Toothless is seen along Hiccup when he offers Mik a shovel. He then assists at Hiccup's speech to Berk. In the Great Hall, Toothless jumps on a tired Hiccup, distracting him from his thinking. While at first Hiccup is mad, he then scratches Toothless and the book ends.

=== ''Fighting the Silkspanners and the Dragonvine'' ===
After intentionally sealing himself and the Dragon Riders and company in a cave on an unnamed island, Toothless reopens it so they all can fight off frenzied Silkspanners and free the other dragons caught up in the Silkspanner's webbing. At one point Toothless aids Hiccup who is caught in webbing, and later, the other dragons get him out of the sticky webbing. The Silkspanners retreat. Toothless and Hiccup, along with Eret and Skullcrusher, Astrid and Stormfly, Gobber and Grump, and the Twins and Barf and Belch come across an island covered in dragonvine with some seemingly helpless farmers. Hiccup introduces everyone, while some villagers are curious and relatively unafraid about Toothless.

Later, this group splits up and Toothless, Hiccup, Gobber, Grump, Astrid, and Stormfly return to the island with the Silkspanners, where they find a female and her hatchlings. Meanwhile, Toothless unknowingly carried a bulb of dragonvine tucked in his saddle and it grows explosively, poisoning him. Hiccup is distraught for his dragon as the baby Silkspanners suddenly swarm over Toothless and start eating the dragonvine, which in turn suck the toxin out, thus saving him. The group returns to the island, saving Eret, the Twins, and their dragons from the farmers, who were growing the dragonvine to protect themselves and their island from people like Drago Bludvist. The farmers and the riders come to terms, and the farmers welcome the Silkspanners back to their island.

=== ''Falling in Love/Farewell'' ===
By the beginning of the [[How to Train Your Dragon: The Hidden World|third film]], Toothless is still the Alpha Dragon and rules over his flock in a similar manner as Valka's Bewilderbeast. As he raids one of the Warlords’ ships at the beginning of the film, Toothless senses something, turning around briefly to check what it was. After not seeing anything, he decides to leave with Hiccup and the rest of the Dragon Riders. The night after returning, Toothless and Hiccup retreat to a cliffside near Berk where Hiccup looks at his map, and Toothless looks longingly at Hiccup's prosthetic leg. Hiccup asks if he wants it, and then throws it for Toothless to fetch, which he does happily, then after hearing a strange sound, ''Toothless runs to the edge of the cliff and then glides down to the forest.''

Later In the forest, Toothless is wandering around searching for something. He uses his smell to sense where it is. He walks further and further into the forest until he spots a white female dragon (later dubbed a "Light Fury" by Astrid) laying down in a part of the forest. The dragon turns around and spots Toothless, growling at him. Toothless gets scared but then walks closer to the dragon. They stare at each other until a snap is heard and the dragon shoots a plasma blast at a tree. Hiccup and Astrid arrive at the forest. The dragon shoots a plasma blast at them, but Astrid manages to push Hiccup out of the way of the blast and they get thrown far but still survive the blast. The dragon is about to shoot another plasma blast but Toothless stops her. However, the dragon gets scared and flies away from them. Toothless tried to follow her by climbing the trees. But the dragon fires and flies into a plasma blast, heating and turning her scales into reflective mirrors, which allows her to become virtually invisible. This leaves Toothless distressed and lonely.

After the encounter, Toothless becomes a lovesick mess, and is determined to find the Light Fury again. Hiccup and Tuffnut later discover Grimmel's dragon traps in the woods. Grimmel visits Hiccup that night, but the latter has prepared an ambush to capture him; Grimmel manages to escape, burning Hiccup's house in the process. Hiccup rallies Berk's citizens and dragons to leave Berk on a quest to find the Hidden World. and he eventually sees her in the Mid-journey when all of the Berkians are flying away from Berk. Toothless becomes so distracted by the Light Fury's beauty that he almost forgot that she tries to toss Hiccup into the ocean and flies down to save his rider. Toothless becomes disappointed again when she disappears again.

The Berkians settle on New Berk. That night, Toothless wakes up sensing something, consequentially causing Hiccup to fall over and wake up, Toothless leaves Hiccup's hut and notices the leaves moving, causing the curious Toothless to investigate. He smells them and happily discovers that the Light Fury is very close. The Light Fury then appears, which makes Toothless really excited. She growls at him to be quiet, worried that the humans might hear him. She then indicates for him to come with her. Toothless follows her and they stare at each other before he bangs his head into something. Toothless loses sight of her but then spots her on the opposite side of a hut. The Light Fury runs off and so does Toothless. Hiccup leaves his hut, yawning.

The Light Fury flies very quickly while Toothless catches up, running. Toothless stops at the edge of a hill, overlooking a beach, which the Light Fury lands on, watching Toothless. Toothless takes one step off the hill and falls down it crazily. Hiccup arrives but watches from where Toothless was perched on the hill. The Light Fury flirts with Toothless with a mating dance, flapping her wings and prancing in a circle. Toothless discovers Hiccup watching from the hill and notices him make flying gestures. Toothless flaps his wings, but the Light Fury only responds by licking herself in a disinterested fashion. Toothless watches Hiccup do another dance but steps on a stick, causing it to snap and the Light Fury to look at the hill. She doesn't see Hiccup but feels suspicious. Toothless starts flapping his wings very quickly, but goes out of control and then causes the Light Fury to block herself from the sand. She then sneezes and Toothless gets frustrated at himself. He looks at Hiccup who is putting his thumb up and does a chicken dance. Toothless performs what Hiccup showed him but the Light Fury just watches. Then Toothless performs various strange dances, causing the Light Fury to get agitated and Hiccup to facepalm. When Toothless gets too close to the Light Fury, she hits him in the face. She then flies to a branch, hangs down from it, and covers her face with her wings. Hiccup looks worried as Toothless walks to the start of the branch. Toothless points towards the end of the branch with his wing and then walks to the end of the branch. Toothless looks at Hiccup showing him a hand gesture suggesting the branch will snap. However, Toothless bounces up and down on the branch, causing the Light Fury to get more agitated. Toothless finally snaps the branch and falls off of it. The Light Fury, still hanging from the branch, covers her face with her wings again.

Hiccup waves his arms, trying to get Toothless' attention. Toothless looks at Hiccup and feels disappointed, but then spots part of the branch and starts drawing something with it in his mouth. This causes the Light Fury to feel curious, so she drops onto the ground and starts watching him draw. Toothless finishes drawing the Light Fury's face.

The Light Fury steps onto Toothless' drawing and makes Toothless angry. The Light Fury growls, but then Toothless drops the branch from his mouth in awe and the Light Fury looks surprised. The Light Fury walks around the drawing to Toothless, and they stare at each other. Then the Light Fury walks away and takes off, inviting Toothless to follow her. She flies around Toothless while he runs across the rocks, unable to fly on his own. The Light Fury hovers and notices Hiccup is on the hill, which makes her angry and flies off. Toothless tries to fly off with her but he just falls into the lake. Toothless looks at his tail and splashes it into the water angrily. Hiccup looks upset and thoughtful.

Hiccup eventually makes Toothless an automatic tail fin that enables him to fly off on his own and find the Light Fury. The two dragons are reunited as they soar into a storm together. The Light Fury shows Toothless how she is able to cloak her entire body by flying into a plasma explosion and asks him to do the same. After a couple of failed attempts, Toothless unknowingly channels lightning into his body to amplify his plasma blast, which allows him to become invisible. As the two dragons ascend above the storm, Toothless licks the Light Fury on her head, which prompts her to swoon over him. They then fly together towards the Hidden World.

As the dragons of the Hidden World accept Toothless as their Alpha, Toothless and the Light Fury dance together to officially become mates. The tender moment is inadvertently interrupted when Toothless realizes that Hiccup and Astrid are being chased by the other dragons, forcing him to leave his mate behind.

Toothless is initially saddened that he has to leave the Light Fury behind, but becomes ecstatic when he sees that she has followed them back to New Berk. The reunion is cut short when Grimmel captures the two of them and forces all of Berk's dragons to surrender themselves to the Warlords.

During the battle, Grimmel uses Deathgripper venom to enslave the Light Fury, Toothless, and Hiccup chases after them but they are unwilling to beat the hunter while he is controlling her. Toothless then uses his cloaking technique to electrocute Grimmel's Deathgrippers that are surrounding him and Hiccup, causing them to fall to their deaths, and fly around Grimmel as Hiccup glides off to rescue the Light Fury. Grimmel manages to tranquilize Toothless midair and Hiccup, realizing he cannot save Toothless by himself, frees the Light Fury instead, and tells her to save Toothless before falling down with Grimmel. The Light Fury successfully rescues Toothless before coming back to save Hiccup, while allowing Grimmel to fall to his death.

The battle won, back on the island, Hiccup fully realizes that the dragons will likely never be safe in the human world and that the Hidden World is where they truly belong. With great sadness, Hiccup and Toothless bid farewell to each other as all of the Berkians set their dragons free. Toothless and the Light Fury then lead the dragons to the Hidden World.

9 years after the dragons left New Berk, Toothless and his mate have three offspring. Each inherits the mixed characteristics of their parents, and went to visit Hiccup, Astrid, and their two children, Zephyr and Nuffink, in ''How to Train Your Dragon: Homecoming''. Hiccup's family later sail across the sea to visit Toothless, the Light Fury, their three offspring, and Stormfly at the edge of the Hidden World, where Hiccup vows that until mankind can coexist peacefully with dragons, the dragons will stay hidden while the Berkians guard their secret.

== References ==
* [[File:CC-BY-SA icon.svg|50px]] Text was copied from [https://howtotrainyourdragon.fandom.com/wiki/Toothless_(Books) Toothless (Book)] and [https://howtotrainyourdragon.fandom.com/wiki/Toothless_(Franchise) (Franchise)] at How to Train Your Dragon Wiki, which is released under a [https://creativecommons.org/licenses/by-sa/3.0/ Creative Commons Attribution-Share Alike 3.0 (Unported) (CC-BY-SA 3.0) license].
<!-- Inline citations added to your article will automatically display here. See en.wikipedia.org/wiki/WP:REFB for instructions on how to add citations. -->
((reflist))

== Further reading ==
* ((Cite book |last=David |first=Erica |url=https://books.google.com/books?id=4Q0GAgAAQBAJ |title=Toothless: A Dragon Hero's Story |date=6 May 2014 |publisher=[[Simon Spotlight]] |year=2014 |isbn=9781481419291))
* ((Cite book |last=Gallo |first=Tina |title=Night Fury and the Light Fury |date=May 2019 |publisher=[[Penworthy Company, LLC]] |year=2019 |isbn=9780876179970))
((How To Train Your Dragon))

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