in the longest day episode, toothlesses ability to take advantage of a situation was incredible! im talking about that moment at the end where hiccup is out of ideas so toothless makes that green enourmous dragon plummet to the water! and also now that i remember that time when he tricked the razorwhip in stryke out! thoughts?
What is wonderful about Hiccup and Toothless is that they are a team. It’s not just a young man riding on the back of a dragon telling the dragon what to do: rather, it’s two intelligent heads tackling a situation together. In Riders of Berk, Hiccup has the Dragon Academy members do exercises which place them in the trust of their dragons, such as flying through tight trees and letting the dragon make the decisions, or falling off the back of a dragon and expecting their ride to catch them before they crash into the sea. Hiccup doesn’t just tell dragon riders to act this way, though; he speaks like this because he has first-hand experience about how important it is to pay attention to Toothless.
The truth is, Toothless takes a lot of initiative when it comes to enacting decisions in tight situations. He makes some advantageous moves in dangerous moments like battles.
Even harking back to the first film, Toothless is critical in besting the Red Death. In fact, after Stoick saves Toothless from drowning, it is Toothless who gestures to Hiccup to hop onto his back so they can fight the beast. Toothless is making an intentional choice here to engage with the Red Death. He’s not doing this because Hiccup is steering him; Toothless is doing this because he has a mind of his own willing to engage in the battle.
Toothless demonstrates even more initiative and decision-making in How to Train Your Dragon 2, when he decides to fight the Bewilderbeast and become the new alpha. Hiccup is not even on Toothless’ back at this moment. Rather, Toothless takes the initiative himself to fight the Bewilderbeast. And as you point out, Toothless can be rather clever in what he chooses to do. Toothless’ bold defiance against the Bewilderbeast helps the other dragons pull free from that dragon’s mental grasp, too. Then, not only can Toothless stand up against the Bewilderbeast, but an entire hoard of dragons can fight against it.
Again and again, we see Toothless making his own personal tactical choices. Toothless makes some intelligent maneuvers when he works with Snotlout to rescue Hiccup in “Defiant One,” helping Snotlout acquire needed supplies and more. Toothless manages to get out of his own cage when he is captured by the Outcasts, too. He takes advantage of the Outcasts coming into his cage, attacks them, and manages to fight them off and leave his prison.
And, as you point out here, Toothless makes some interesting, advantageous decisions in Stryke Out and The Longest Day. Toothless appears to have a strong head on his shoulders, and especially, he seems to be very good at making great calls in the midst of heated battle.