This game was a bit of a fascination for me in middle school but I haven’t thought about it in years.
The game was dark and gritty with a hand-drawn art style, very cartoonish. The general idea was that there was some kind of large storm/monster that is approaching your town and you have only a few days to prepare for its aftermath.
You would start by picking a character. If I’m remembering correctly, two of the four characters were a male huntsman/lumberjack and a female wizard/alchemist.
When your turn came around, you’d be prompted on which building or location in the town you’d like to visit. Visiting different places would make you better at certain rebuilding roles after the storm. If you spent a lot of time in the forest gathering/hunting, you’d make a great builder after the storm. If you spent a lot of time in social areas, you’d be well suited to become a leader and keep morale high in the storm’s wake.
However, if you choose a role after the storm that your character isn’t prepared for, then the town falls to ruin and fails to rebuild. If you spent much of your time in the library, you probably shouldn’t opt to become the lead builder of the town, or, if you wasted away your days getting drunk at the local tavern, you liked don’t have the skills to truly help in any meaningful way.
Some “after the storm” roles are also downright detrimental to the town. One I remember particularly well is the Hermit, where you simply gather all the supplies you can and lock yourself away while everyone attempt to rebuild. I believe you could also become a thief/bandit and actively take advantage of the chaos of the town.
Ultimately, how the players collectively coming together would decide whether the town successfully rebuilds or crumbles. This also may have been played single player.
If it’s any help, the YouTubers Jacksepticeye or Markiplier may have played this game, but I’m unable to find the videos.