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Hooligan Tribe in general -
Living on the island of Berk, the Hooligan Tribe has undergone great social change in recent years. Whereas once they fought a long, bloody war with the dragons, now they have made peace with them.
Badass Army: Subdued compared to other examples in the franchise, but with dragons they manage to defeat threats they greatly feared. Even without dragons, however, they can hold their own.
Dragon Rider: The first of the Viking tribes to actually perform this thanks to Hiccup.
Had To Be Sharp: Elements of this due to the constant dragon attacks they had to face.
Horny Vikings: Many helmets have horns. Dragon horns perhaps?
Proud Warrior Race Guy: Downplayed. They play many of the tropes straight, but are generally peaceful when not attacked.

Hiccup alone -

Hiccup Horrendous Haddock III

Voiced by: Jay Baruchel (film and TV series)

Adorkable: There's been plenty of fan gushing at how cute the geeky Hiccup is. This should really be expected when he's voiced by Jay Baruchel.
Aesop Amnesia: In "Terrible Two", he causes problems because he trusted a strange dragon over Toothless. He didn't learn his lesson because in "Heather Report", he trusted a strange girl over Astrid. Downplayed in "We Are A Family Part 2", where he is very reluctant to trust Mildew but ultimately does so. Like the previous occasions, this is a horrible idea because Mildew used him to learn dragon training which he passed onto Alvin. A storyboard of an unused intro by Hiccup says this has less to do with amnesia and more to do with Hiccup simply being too trusting.
All-Loving Hero: Believing that humans and dragons can coexist will definitely make him this. Deconstructed in the series, where his habit of trusting people immediately has led to problems.
All of the Other Reindeer: Nobody likes him. He's the village pariah because he's scrawny and usually messes everything up. In keeping with the trope, things get better for him after he ends the Dragon Wars. In the books, Snotlout nicknames him 'Hiccup the Useless'.
Alliterative Name: Hiccup Horrendous Haddock III. It's never said in full in the movie but it's canon.
Amazon Chaser: A large part of his crush on Astrid is because of her Action Girl-ish qualities. Take a look at her introduction: she's fighting dragons amid flames and Hiccup has the 'hearts in his eyes' expression. This moment in a tie-in game has Hiccup gushing over Astrid destroying a ship.
Artificial Limbs: Hiccup loses his left foot during the battle with the Red Death in the movie. It's replaced with a metal prosthetic. Leads to Angst? What Angst? as he seems to adjust to it very quickly. In the series other characters make a bigger deal out of it than he ever does. By the time of the second movie, he has given the prosthetic a bit of a transhuminist utility in being able to quickly switch between a latching foot for when on Toothless's saddle to a hoof-shape foot for ground walking.
Archer Archetype: Though he is on the warmer side of the things compared to colder examples of this trope.
Asleep for Days: Hiccup wakes up several days after the final battle with Toothless watching over him. In the books, however, he is asleep for days and wakes up just in time to see Toothless wake up while being burned alive in a Viking funeral (he went into a healing sleep coma after badly injuring himself saving Hiccup from the Green Death) and then fly through the sky on fire, before extinguishing himself.
Awesomeness by Analysis: His awesome dragon skills came from study.
Awesome Moment of Crowning: Becomes Chief of Berk following his father's death in the second movie. After the final battle, Gothi draws the Chief's symbol on his forehead in charcoal, and the entire village erupts in chanting "Long live the chief," and the dragons light off some fireball fireworks.
Badass: Firmly so by the climax of the movie. The TV Series expands Hiccup’s growth as a Guile Hero. So far, he pretty much is a top contender for Berk's biggest one.
Badass Adorable: Berk's first dragon tamer and best inventor also happens to be a sweet, somewhat insecure teenage boy.
Badass Bookworm: Hiccup develops into one through the story and may become a full-fledged Gadgeteer Genius.
Badass In Charge: Becomes the leader and head teacher of Berk's Dragon Academy while still being a Badass. Then he becomes the Chief of Berk after the end of the second movie.
Badass on Paper: He looks like a scrawny teenage kid with a knack for inventing, but he did create the art of dragon taming, ended the war, and instigated the demise of the Red Death.
Badass Pacifist: His role in the movies, since the "Vikings vs. dragons" conflict doesn't exist in the books. His ability to tame dragons comes from Hiccup being friendly instead of defending himself. This takes more courage than killing them on sight.
Badass Teacher: Slowly becoming the second part as the main teacher of the Dragon Academy.
The Beastmaster: He learns how to tame and train dragons.
Beware the Nice Ones: Hiccup is a very pleasant person and easy to get along with, but he can be quite terrifying if you piss him off. Dragon taming aside, he displays his anger in "Out Cast Part 1" where he gets furious with Snotlout in regards to getting Astrid in danger, and suspends him from the Academy. The rest of the children were surprised to see him like this. Keep in mind he ended the war with the dragons by killing the Red Death, and he is very protective of his dragon and friends. Dagur the Deranged discovered this the hard way.
Big Good: Becomes the Chief of Berk at the end of the sequel, with Toothless as the Alpha.
Big Ol' Eyebrows: Just look at that picture!
Bigger Stick: Discussed. His friends sometimes wonder how much of his success is due to his own skill, and how much is due to being the rider of an absolutely fantastic dragon. Of course, when they attempt to test this by having the group train Terrible Terrors, Hiccup quickly teaches his to blow things up with impressive accuracy.
Black Sheep: In the movies, as an inventor and scientist in a society of warriors.
Born in the Wrong Century: In the 21st century here, Hiccup might be bullied, but at least he'd have a niche in society where he belonged, and his intelligence would be recognized. In the films' setting, he's treated as a child and disowned by his family and tribe for trying to train a particular species of animal instead of killing it on sight. Instead, he has to make his own niche.
A Boy and His X: A Boy And His Dragon. With Toothless of course.
Braids of Action: Gets these in the sequel. According to Word of God, they're Astrid's handiwork (she can even be seen doing so early in the film) and that Hiccup isn't necessarily fond of them - but he leaves them in for her sake anyway.
Brainy Brunette: In the film and TV series.
Break the Badass / Break the Cutie:
In the first film, Hiccup has spent his entire life being the black sheep of his village. His father being openly ashamed of him. His peers constantly mocking him (except Astrid and Fishlegs). All resulting in him having poor self-esteem. And when he finally finds a friend in Toothless and tries to demonstrate that humans and dragons can co-exist, his father stops it. In the next scene, Stoick disowns Hiccup, almost bringing Hiccup to tears. Fortunately, his father does apologize. And after the climax, he lost his leg after taking down the Red Death.
Gets worse in the sequel: He tries to persuade to madman Drago to stop enslaving dragons and not to go to war. Drago instead makes his Bewildebeast mind control Toothless and order him to attack Hiccup. Stoick saves his son at the last minute. But is killed fatally by a Mind-Controlled!Toothless's blasts.
Broke Your Arm Punching Out Cthulhu: In this case, Lost Your Leg Punching Out The Frackin' Huge Volcano Dragon. His lack of angst about this implies it was Worth It.
Butt Monkey: In the books to almost everyone else because he was born to the chief of the village. He feels very inadequate compared to the tough warriors he's descended from.
Catch Phrase:
"Thank you for summing that up."
"You just gestured to all of me."
"Let me show you."
The Chains of Commanding: Felt that when he had to consider kicking Snotlout out of the academy. His father pointed out that he can't always be both a good friend and a good leader at the same time, and that as a future chief he will have to put Berk above himself and his friends.
Chick Magnet: Hiccup has won the affections of both Astrid and Ruffnut, the former who he started a relationship with. Hiccup has the largest female fanbase of the entire cast, except maybe Toothless.
Classical Anti-Hero: Originally a Type one, a wimp who nobody really likes. Compared to the paragon hero his father acts like, Hiccup's runtiness is constantly mocked. Even his ingenuity in making newer weapons was mocked because while being smart about hunting and trapping and killing dragons is a good thing, none of what Hiccup created seemed to work. Eventually, he accepts himself and all his flaws, turning them into his strengths and would become a hero in the eyes of his village.
Crazy-Prepared: Justified though experience. He carries a complete set of spare parts for Toothless' tail fin at all times.
Deadpan Snarker: It's such a defining trait, being held hostage by Alvin doesn't stop him from dishing it out. A lot of the series' funny moments is mostly him and his often witty one-liners.
Dragon Rider: The very first. Or as far as he knows, until he finds his long lost mother.
Father, I Don't Want To Fight: Zig-zagged. Initially he wanted to kill dragons, then lost his nerve but still wanted to make his dad proud.
Hiccup: Three hundred years and I'm the first Viking who wouldn't kill a dragon!
Astrid: First to ride one, though.
Fluffy Tamer: While giving them names like 'Toothless' and cuddling them.
Freudian Trio: With his parents, Stoick and Valka. He is the Superego to his father's Ego and mother's Id.
Friendless Background: Except for Gobber, Hiccup had no friends. That changes during the course of the first movie.
Gadgeteer Genius: He can make an interlocked tail fin for Toothless centuries ahead of when such technology was possible. This may be a reference to the books, where Vikings have fully-operational STEAMSHIPS, hot-air balloons and gliders well before the Industrial Revolution. In the subsequent movies and series, he also proves to be quite adept at new designs...
In the series, he builds a shield with a host of gadgets, including a crossbow (compatible with normal bolts as well as other objects like paint), a grappling hook, and can be thrown. Then he upgraded it with Gronkle Iron, meaning it was lighter than ever and capable of shrugging off hailstorms of daggers and even dragon breath attacks.
For the second movie, he designs two things. One, a flaming sword called Inferno, which when not in use is retracted like a certain weapon of a more civilized age. It also has a compartment to store Zippleback gas which can be released and then lit with the sword. However, more impressive is his wingsuit which permits him to perform short glides alongside Toothless.
In addition, he's shown to have a hand in various engineering tasks around Berk, from dragon roosts in When Lightning Strikes and helping rebuild Berk after Drago's attack. Regardless of his new fame and role as leading Dragon Rider, he still spends time in Gobber's shop too.
Graceful Loser: Discussed. In "Thawfest", Astrid said this was his most admirable trait in her eyes when he began acting unpleasant at the thought of winning the games just to spite Snotlout.
Green Eyes: To show how very different he is to the rest of Berk. One example, while they all rely on brawn and strength, Hiccup would rather use his inventions.
Guile Hero: Stoick wants him to be an Action Hero, but Hiccup is much better with smarts and cunning. In fact, it was due to his intellect that he was the first person to solve a poem-based puzzle that nearly destroyed Stoick's and Gobber's friendship. This was because the puzzle was created by a Guile Hero himself. That said, Hiccup has become quite capable physically by Defenders of Berk, facing off with Dagur the Deranged in single combat while Toothless was trapped by bolas.
Handicapped Badass: As a result of the first movie.
The Hero: Hiccup is the one trying to keep stability and peace between dragons and Vikings.
Heroes Prefer Swords: His main weapon in the second movie is listed as the blade. It lights itself on fire and just like his shield it has a host of utility tools befitting a Gadgeteer Genius.
Heroic Self-Deprecation: Often uses his sarcasm to make fun of himself on occasion. At comedic and dramatic moments.
Heterosexual Life-Partners: An inter-species example. With Toothless, a Night Fury dragon.
He's All Grown Up: Let's just say he's gotten over his awkward adolescence phase in the second film...◊
Hometown Hero: Fully becomes this in the sequel. Now, whenever something goes awry in Berk, they know that Hiccup has a plan.
Huge Guy, Tiny Girl: While this trope isn't applicable in the first film, it is played straight in the sequel with him and Astrid.
I Call It "Vera": His sword in the sequel is named Inferno according to The Art of How To Train Your Dragon 2.
I Just Want to Be Badass: At the beginning of the film, Hiccup desperately wants to be like the other Vikings and kill his own dragon; "Normal" in Berk is "badass."
Insecure Love Interest: In the first movie, a deleted scene has Hiccup sarcastically and truthfully believe that Astrid "wouldn't come near him if she was on fire and he had the last bucket in Berk."
Interspecies Friendship: With Toothless, of course, more so than the other riders with their dragons since Toothless is much smarter.
In the Blood: Oh yeah. Hiccup inherited his father's willingness to protect others no matter the personal cost and his mother's kindness and way with dragons.
Jock Dad, Nerd Son: His first scene shows a miniature ballista he invented because he couldn't heave the projectile himself. His dad is not impressed.
Kid Hero: He's fifteen and ends the 300 year dragon war. No longer the case in the second movie where he is 20 years old.
Missing Mom: Averted in the books, though his mom rarely even shows up there until "How to Seize a Dragon's Jewel" and onward. Played straight in the movie where it's heavily implied that she was killed by a dragon, which explains Stoick's attitude toward them. Hiccup is quite afraid of forgetting her in Riders of Berk. It turns out she's alive in How to Train Your Dragon 2, and every bit the dragon trainer Hiccup is (and then some).
Large And In Charge: He is the tallest of his friends in the second movie, and all of his friends acknowledge him as their leader.
The Leader:
Of the Dragon Training Academy in the series. Type Charismatic because he's also The Face of the academy against old prejudices.
Continued in the second movie, except now as the chief of all of Berk.
Leitmotif: A tin whistle is a recurring instrument in his scenes, which ranges from comedic reels to beautiful melodies.
Like Father, Like Son: Hiccup and Stoick act exactly like each other. They even quote ones another in the first film without ever realizing they did it. Takes after his mother too. In the second film, it's revealed that Hiccup's Missing Mom has been doing what he learned in the first film for twenty years.
Living MacGuffin: Alvin wants him for his dragon-training abilities.
Luckily My Shield Will Protect Me: As of "The Iron Gronckle", he has a shield made of Gronckle Iron, which is very tough and very light.
Martial Pacifist: Hiccup may be inclined towards diplomacy and in the second movie styled himself as the peacemaker, preferring to use words over weapons, but when battle calls leaps into the fray without hesitation. He'd just prefer not to have to get to that stage.
More Dakka: Has a particular fondness for using this in dragon combat, bombarding the enemy with a hail of highly accurate shots. It becomes obvious that this is his preference rather than just a Night Fury thing when he trains a Terrible Terror to do it as well.
Nice Guy: Hiccup is a kind, brave, compassionate person. Heck, while his defining flaw may be his pride, it's not the usual arrogant example.
Not So Different:
With Stoick. It takes a while for both to realize they have the same hardheaded tendencies about things they truly believe and won't listen to arguments against it lightly.
With Toothless. A significant turning point in the film is when he musters up the courage to look into Toothless' eyes. Upon seeing the fear there, he realizes that dragons are not, as he'd been taught from childhood, a mindless Always Chaotic Evil race that wants to kill everyone.
With Drago in the sequel. Both grew up fearing dragons. Both overcame that fear and realized dragons could work with humans. Both even have artificial limbs opposite of what they use in taming dragons (Hiccup lost his leg but uses a gentle touch with his hand, Drago lost his arm and uses a harsh boot). However, unlike the above examples, this does not end positively.
Official Couple: He and Astrid are going stronger than ever in How to Train Your Dragon 2.
Pride: Hiccup's defining flaw. It leads to brash and rushed behavior several times.
In the first film, his pride in his still-not-fully-working gadgets led to him rushing out ill-prepared into a battle right at the start of the film.
In the second, his belief in himself as a peacemaker after he got Alvin and Stoic to become allies once more and his refusal to listen to his father about Drago led to him deciding that the best way to find this madman was being captured, and his holding Toothless back from firing rather than just aim to take Drago out sooner led to his own father's death.
Red Is Heroic: In the sequel, Hiccup's new suit includes Berk's symbol painted red on one of his shoulder pads.
Relationship Ceiling: His relationship with Astrid is held back in the TV show, although the Ship Tease is rampant. Averted in the sequel, where they're clearly a couple (and possibly engaged to marry, as Stoick calls Astrid "my future daughter-in-law").
Scars Are Forever: He has a small, very faint scar on his chin that's only visible during certain scenes in the first film. In the second film it's revealed that he got it when he was accidentally scratched by Cloudjumper as a baby, and it's also how Valka is able to recognize him after twenty years.
Science Hero: Along with wit, Hiccup also prefers to resort to his amazing inventions and gadgets to help.
Shrouded in Myth: It's implied (in the "Portrait of Hiccup" episode) that no matter what Hiccup does, Viking mythology in the future will portray him as a fearless, tough, fire-breathing badass admired by everyone- because that's what Vikings do. They make awesome ballads out of their heroes' exploits even if they must warp the truth to do it. Hiccup finds this exceedingly depressing since he spent his whole childhood ignored and degraded because he didn't fit Viking standards of strength.
Stepford Snarker: In the first film he uses sarcasm to cover up his loneliness at being Berk's Black Sheep.
The Southpaw: Shown subtly in the film, which is accurate to the book portrayal. Hiccup writes with his left, and any closeups on his control of Toothless' prosthetic tail-fin are on the left stirrup. His clumsiness may be a factor of having to use right-handed objects, or his weak hand, or both.
Swiss Army Weapon: His own invention and personal weapon, it's a shield that can be used not only as a shield, but also fires a grappling hook and transforms into a crossbow.
Tranquil Fury: He was very angry with Snotlout in "Cast Out Part 1" when his latest attempt to hog the glory almost killed Astrid, keeping composed as he sternly told him he was suspended.
Underestimating Badassery: A lot of people tend to think Hiccup is just the scrawny, nerdy, weirdo...then they actually see him in action.
Weapon of Choice: He always carries his dagger.
"Well Done, Son!" Guy:
In the movie he never quits striving for his father's respect, but as the story progresses he's able to put other priorities first.
Despite Stoick's acceptance of dragons in the series, Hiccup still has some hang ups.
Who Names Their Kid "Dude"?:
In the movie, Hiccup points out how ridiculous his name is, but explains the reasons for awful names (scaring off gnomes and trolls) and says that there are other people with worse ones.
In one episode of the series, Hiccup mentions that it's traditional to call the runt of a litter a 'Hiccup'. It ends up being a key point later in learning he wasn't the first chieftain son to be a Hiccup either.
Youthful Freckles: Hiccup has a lot of them as a teen and keeps a few as an adult.