Without the doubt the funniest (and simultaneously the saddest) thing about The Nine Realms is that Dragon Club learns about Hiccup as this great leader, this Dragon Master, this masterful strategist, and Tom practically worships him and tries to live up to him (Hiccup is totally not his father figure even in death or anything like that) and none of them will ever know just how unhinged he was in life. Only outdone by the twins.
Made a diving bell to reach the bottom of the sea to free a Submaripper.
He tried to get his village on the side of dragons by throwing his helmet (made from his then assumed very dead mother's breastplate) and proclaiming he wasn't one of them and then patting a trapped Monstrous Nightmare on the nose.
His plan to defeat the Red Death, a dragon nearly the size of a volcano, was to blow it up from the inside out.
He dealt with one of Dagur's plans by using Smokebreaths to take his fleet apart nail by nail.
Nearly threw hands with an old man when Mildew said something about dragons he didn't like.
He famously threw himself off a cliff to prove his invention worked. It didn't and his conclusion was "time for Dragonfly 2!"
He tried to talk a madman out of his warmongering.
15 years old and talking shit to men twice his height and thrice his size.
Made a firesword and flightsuit just because he could. (and because he really, really wanted to be like a dragon.)
He wanted to get through a barricade made out of living, breathing Typhoomerangs spewing fire at them by flying down the middle of the fire and then waiting them out. And it worked!
Honestly, you can just keep going on and on about him.
Hiccup was unhinged and Dragon Club will never know.