How did you run it? WineHQ lists compatibility as "Gold", but report is three years old. Might be worth trying it out on latest Wine version.

Had some luck with Windows version of Obsidian. Using Ubuntu 20.04, should work on other distributions too.

1. Install wine and timidity. I presume xephyr server is installed.

2. Insert CD and run setup.exe with wine. Install game to default location, install QuickTime when it asks.

3. In one terminal window run timidity midi server (if you want background music): `$ timidity -iA -B128,8 -Os`

4. In another terminal window start the game like this: `$ Xephyr :1 -ac -screen 640x480x16 & DISPLAY=:1 wine "C:\\Program Files\\Segasoft\\Obsidian\\Obsidian.exe"`

In case you don't have physical optical drive you can use CDEmu to mount disk images, but it has to be installed from additional repository and has a bit of complicated setup.

Obsidian has a Mac port. Have you tried running it under SheepShaver? You may have better luck there.

I have been playing a bunch of old Mac games on SheepShaver. Sometimes they just work better than the Windows versions under Wine.

I'm glad someone else remembers this forgotten gem. Every couple of years or so, I try to get Obsidian running again. No luck so far. :(