All
Have Diablo running on a 2011 macbook pro - OSX 10.7.4 with CX 11.2 - in "windowed" mode and with a patch that requires no "physical" media - googlefu that. Also googlefu that last patch - Diablo 1.09, plus copy the large data file to your diablo install directory
(I have the original CDs and had to run vbox to copy the windows files to a folder so I could run the installer)
There is a long standing issue with no menus - just black screen -- but hit enter twice and you will find your self in game.
See this thread:
http://appdb.winehq.org/objectManager.php?sClass=version&iId=3498
From the above thread:
DIABLO via CX
Since the screen is black while using the main menu, here's how to start a new game and load a saved game.
To start a new game:
- Skip the intro with Enter.
- Wait until you hear sound.
- Press Enter (selects "Single Player").
- Press Enter (selects "Warrior", if you prefer "Rogue" or "Sorcerer", press the down arrow once or twice respectively.)
- Enter your characters name.
- Press Enter (confirms your name).
To load a saved game:
- Skip the intro with Enter.
- Wait until you hear sound.
- Press Enter three times (selects "Single Player", then "Select Hero", then picks your hero).