Ok, running from the command line from the directory in which the application is installed gets me further: $ cd ~/.wine/drive_c/Program\ Files/BOH/ $ /Applications/Darwine/Wine.bundle/Contents/bin/wine BOH.exe This causes a window to open with the title "SDL_app". The game does run in a window, but doesn't have SDL_app as the window title. The window is completely black, the keyboard has no effect, and the title music doesn't play. So the game doesn't seem to get further than opening its window. The game does run under Wine in Ubuntu, so I'm really confused about what's going on!