TaskMaker (1989)
Vote to bring this game to GOG and help preserve it.20
This game never saw wide market as it was a Mac exclusive from the very early 90s. Though it did do well enough in even that limited market to get a sequel: Tomb of the Taskmaker.
It was ahead of it's time in a few ways. I think I can fairly safely say that I've never seen a game with poetry written in (not on) the walls. Nor a game where dying sent you to Hell where you can escape. Bribe your enemies into leaving you alone. Get drunk. Eat some Bef - Real Fud. Deposit your money at an ATM. It is a game that is chock full of secrets and an irreverent sense of humor and even came with an editor.
I can all but guarantee that if this had had a Windows release, it would already be on GoG.
Now if you'll excuse me. Excuse me. Excuse me. Excuse me. GET OUT OF THE WAY!
If I remember correctly, this game (maybe it was the sequel or both?) had a great feature I wish other games would copy. When you finish the game and become the "Taskmaker", you unlock an ability that basically turns the entire game into the map editor. I played this a lot when I was young (there were only 4 games on mac at the time; this, Zork, Breakout and Super Breakout) and I would cop it immediately if it showed up on GOG.