Hi,
I have the same problem.
Parallels 15 Desctop for Mac Home Edtion, Host: Catalina 10.15.1, Guest: Sierra 10.12.6, iTunes 12.8.2.3
Black screen when I try to watch my purchased iTunes movies.
Paralles support checked a couple of settings and then referred me to Apple.
Apple Support has referred me back to Paralles. According to Apple, the problem lies with Paralles.
Can someone help me?
Best regards, Siegbert
I think I'm getting the exact same thing - It looks like it is specifically a problem with iTunes DRM video. I confirmed I could play my own videos in the same format and they worked via Quicktime. One "Theory" (and look, it might not be valid) is that it could be related to iTunes thinking your video is on an "invalid" display (a projector, rather than an internal monitor). Like I said it's a theory...