An underrated gem from 1991, Castles was this wonderful mashup of navigating medieval politics, building a castle, and withstanding sieges. How could I not love it? At heart, it was about designing your fortress and citadel, like that beloved old illustrated David Macaulay classic book about castle construction had come to life. You laid out your towers and walls, hired and fed builders, and watched as the superstructure blossomed. Time was of the essence, as the heathen Picts of the countryside were wont to attack and dismantle your emerging greatworks if they were insufficiently defended by archers and footmen.
What gave Castles an added dimension, though, was the through-line of text-based choice architecture that ran in parallel. Your king, as he awaited the completion of his royal seat, was beset by duplicitous courtiers, marriageable daughters, wayward priests, restless neighboring rulers, and more. Each of your choices was a balance between who you pissed off and who you placated - no perfect answers, just choices with consequences. It was the most realistic representation of civic leadership I've ever seen in a video game.
I played this again not long ago in a fit of nostalgia. Like so many things from when I was sixteen, it struggles to bring me the same kind of joy now that I'm nearly fifty.