You Don't Know Jack: Volume 2

You don't know jack

I just tested this running in Wine on Ubuntu. The game worked perfectly. The package includes a .BIN and a .CUE file that can be converted into an ISO using bchunk.

Here's my recipe for making it work in Wine.
# prework - create the CD ISO
sudo apt install bchunk
cd ~/Downloads/YDKJ/cd
bchunk cd.BIN cd.cue you_dont_know_jack.iso

# mount the cd
sudo mkdir /media/wincd
sudo mount -o loop -t iso9660 ~/Downloads/YDKJ/cd/you_dont_know_jack.iso /media/wincd
sudo ln -s ~/Downloads/YDKJ/cd/you_dont_know_jack.iso $HOME/.wine/dosdevices/d::

# start the program
winefile
# Go to home/larry/Downloads/YDKJ/SIERRA/YDKJ/ and double click on YDKJ101.EXE