Various versions Jeopardy! Won't Work

[B#MajorGeneral]

[Working with WINE: Version 1.8-rc4 on Mac: OS X Version 10.9.5]

I was hyped whenever I got some other games to work with Wine, so I thought to play my favorite trivia game: Jeopardy! 2003.

However, after installing it, the screen goes full, small, and the application crashes. The same thing happens for Jeopardy! 2nd Edition. (For whatever reason, I suspect it's the opening video or something to do with the media files, but I have nothing to prove it.)

Plain ol' Jeopardy! is another story. It installs, but whenever I try to play it, it informs me that it can't find the CD-ROM. ("You must have the JEOPARDY CD-ROM in your drive" to be exact.) I made sure the physical CD was seen as a CD-ROM drive under config, but nothing. I also transferred the files to a folder on my computer (the Mac), indicated that it was a CD-ROM drive, but it still won't work.

I just really want to play one of them.