When I was young and had a super nintendo I loved playing Super Mario RPG.
I’m playing the remake and I’m at the scene after defeating Valentina. Mallow goes into the castle and Mario was left standing outside.
Back then I didn’t know why Mario pulled out an umbrella and it rained. I just realised after 20 years of playing the original that Mario knew it was going to rain because whenever Mallow cries it rains; Mario knew that Mallow would get all emotional when meeting his parents for the first time.
Blew my mind.
It would probably be the Milkman episode of Psychonauts. The storyline and subtext of the episode are not overly complicated, but analyzing the psychology of the character took me quite a while. I still think it’s one of the best side stories I’ve ever seen in a video game.