Holiday World Tycoon

Holiday World Tycoon is the sort of game that feels like it was designed after someone spent a bit too long staring at a postcard rack in an airport gift shop and thought, “Yes. This. But interactive.” Released in 2004 for Windows, it cheerfully drags you through a patchwork of seasonal mini-adventures, each one feeling like it was built by a different cousin at a family reunion—some talented, some… well, enthusiastic. The game throws snowflakes, beaches, fireworks, and questionable fashion choices at you with equal enthusiasm, and while none of it is groundbreaking, it somehow manages to charm you into continuing.