100% honesty here, the third movie killed my motivation to finish this. However, I had already begun to write it out and I hate to let the work waste away in my drafts… So, I’m going to leave what I wrote and give a semi-ending to this. I hope you enjoy.
Summarizing part 2, when given freedom, Hiccup is shown to excel. As he excels, he grows into someone fit to lead and gains the first of his loyal (human) companions–Astrid. In gaining Astrid’s faith as a leader, the others begin to follow him too.
As HTTYD1 ends, we see that some of Hiccup’s ideas are being implemented and people are cheering for him as the one who saved Berk from the Red Death and united them with dragons–BUT life isn’t all sunshine and roses! As the show Dragons: Riders of Berk reveals, Hiccup has a long way to go to become the next chief not just in gaining leadership skills, but in gaining trust and support from and towards those around him as a future leader.
Stoick, a classic Viking, seems to have followed this tradition almost fully (the only real difference being that Stoic inherited his role, but even with the inheritance he has earned the right to be chief through his deeds). Each member of Stoick’s council is fiercely loyal to him–even Spitelout who is narcissistic and prideful is loyal to his core to Chief Stoick. The whole of the council is also a little afraid of him, knowing full well that Stoick can and will do what he wants and that they must, as loyal warriors, follow his lead.
*According to the fan wiki, when Stoic the Vast was alive the council consisted of: Gobber the Belch (Berk’s blacksmith/former warrior/dragon doctor), Spitelout Jorgenson (warrior/Chief’s 2nd in command), Silent Sven (Berk shepherd), Bucket (farmer/fisherman of Berk), and Mulch (farmer/fisherman of Berk). Also, adding to that list is Gothi who, while not a member of the council, has a strong role in decision making as the village elder. (Before someone points out that Bucket and Mulch are fishermen, let’s note that all of their wikis have some mention of being fighters/warriors in their past.)
Hiccup is a little different though–and so are his team of dragon riders. What I think we’re seeing within the series is, essentially, the rise of a king rather than the rise of another chief. It’s not a perfect analogy of what’s happening, but it kind of sets up the foundation for character growth we see over the course of the first two movies and shows. Firstly, the foundation for a kingdom rather than a chiefdom is already there, starting with how the chief has been decided through a family line while other important roles seem to have been acquired by individual power like Gothi choosing who gets to kill the first dragon at the end of training for the young Vikings in HTTYD1. While Hiccup is unlike to be made “King” by the end of the series, he is certainly going down in the Berkian history books as a different kind of leader because of the choices he makes and because of how the rules.
Rather than picking the strongest of the group, he has a collection of different people with different abilities and skills (the dragon riders). Over time, and through heavy encouragement/leadership by Hiccup, the dragon riders each develop significantly (well, maybe not so much Astrid as she has always been pretty mature). Of the twins, Ruffnut shows some hidden wit and, on more than one occasion, shows the capability. For example, on more than one occasion in the show, Ruffnut is shown to be able to put aside her selfish desires, as well as her brothers, in order to do what is best for the group. There is even an episode devoted to such in later seasons. In movie one, heck-even early in the show, this was something no one would have expected given her behavior. However, she’s changed and by extension, the audience is able to see that Ruffnut is actually much smarter than she appears and seems to be acting the way she does in part out of her own fun but, more likely, out of protectiveness for her brother who is sensitive but also much more impulsive and childlike than others their age. Fishlegs gains an enduring strength as the series go on, something hinted to in the first movie but really comes out in the show. Snotlout perhaps shows the most development though as he goes from complete impulsive muscle-headed mightier-than-thou to a loyal companion and, perhaps, a trusted confidant to Hiccup by the end of the show. Overall, by the time movie two comes about, we see the development climax in scenes like Drago’s capture Astrid & company. In the scene, the group laughs at the idea that anyone can take on Hiccup when it comes to controlling dragons. Something that the last season of the HTTYD shows also seems to make a note of (that being that Hiccup has a special way with dragons).

Regardless, Hiccup’s attention to his group and different form of “ruling” them (not just ordering around like his father but attempting to get his team to understand why he does what he does), creates a different feel to what we can expect of him in the future.
It’s thought to be that “kings weren’t just more powerful rulers; they were also a different kind of rulers…the king’s followers had much more specialized roles in both war and peace.” From what we’ve seen, Hiccup is attuned to this specializing on deciphering times for peace and times for war, ultimately hoping for peace more than war but willing to fight when needs be. Likewise, he’s worked hard to change the dragon rider’s way of thinking to match. Snotlout being an impressive example of someone who, while still prideful, shows a lot of improvement across the animated shows by learning to care for his friends and not just chicken out when there’s no one to show off to. Ruffnut also shows great improvement, as she learns to set aside the crazy she shares with her brother to help the greater good on a handful of occasions. Astrid learns to stop hitting first and learning second, and Fishlegs also learns to be more assertive. Toughnut… well, he tries but his improvement does not seem to be the same level to me, though he does show great talent in trapping.
What I mean to formulate here is that (1) I think the Chief chooses members of the council and I think Stoick chose his members primarily for their fighting power and loyalty. (2) I think that Hiccup will choose differently from his father. I think that his choices will also be fiercely loyal, but they’ll also be people that can think critically about whether to go to war or fight for peace via discussion.
In the end, what we might see is that Hiccup becomes the first King of his people just as Toothless has become a “King” of dragons.
The End.