Stupidity: The Engineer and Fireman of the Polar Express train crew should have known better than to not bend back the the metallic prongs of the cotter pin, which would have prevented the cotter pin from coming loose and causing all those problems in the driving of the train.
Stupidity: During one of the test drives, the hook that Hiccup uses to fasten himself to Toothless gets bent, so he takes Toothless to the blacksmith to cut the line. There are two ways he could have easily avoided this: He could just unhook the saddle, take that to the blacksmith and cut himself loose, or he could just untie the leather strap. What he does here is needlessly risky and just there for his awkward conversation with Astrid.
Stupidity: When Jasmine finds out that Prince Ali is actually the boy she met in the marketplace, she seems to completely forget about Jafar telling her he had been executed. She never asks why he's alive, nor does she even bother to confront Jafar about his treachery.
Stupidity: If the weak spot of the house is the fiery chimney, then why did the kids have to light the dynamite? They put themselves in unnecessary danger for the sake of drama.
Stupidity: Rescuing Manfred and Diego from the giant carnivorous plant, Buck could have cut both wires simultaneously to avoid that unnecessary horrible potential outcome of cutting the wrong one. The wires were stretchable enough for them to have been held together to then get cut at the same time. (00:37:40)
Stupidity: In a flashback scene, a mother, father and daughter are taking pictures of Norm and two other polar bears. The daughter decides to run up to the three polar bears, but the parents appear to do nothing about it. The polar bears could have been a threat to their daughter for all they knew. (00:04:25)
Stupidity: At the end of "You're Welcome", Maui puts Moana in a cave and placed a large rock blocking the only known exit. This means, as far as Maui knows, he's trapped a human in a cave with no food, water or exit as he didn't know Moana could make a very lucky escape. Basically Maui was going to leave Moana to starve to death so he could take her boat.
Stupidity: Just after the geckos have finished eating Josephine's children, Thang, Rose, Didi and Sal attempt to sneak away. They attempt to sneak away from the geckos by walking directly in front of them which results in the geckos spotting them. If they attempted to get away in literally any other direction, the geckos would not have seen them. (00:22:50)