Hello. I am not sure if this is the exact right forum, but I know there is a lot of knowledge on this board and I was hoping to find someone who has some ideas here.

In this case I am attempting to run a piece of software from 1996 called Sting: All This Time. It is a Windows 9x game. I have run it in both DOSBox (using a recent X build) and 86Box. While I do have a 9x machine I can test on, it is packed up and will take some time for me to get it out and running for this. For what it's worth, the setups I am using run the majority of 9x games I have tested without issue.

The "game" itself seems pretty clearly to have been created with Macromedia Director. It is split across 2 discs (EAST & WEST). I purchased the game as I had not see a working copy online, and it was the primary way I could ensure that the discs were not damaged or imaged improperly.

The issue is how the game itself runs. Director worked a bit like HyperCard (the original Myst backend). Static images can be shown and then swapped with multimedia clips. So, for example, a static image of a television could be shown, and when you hit a got spot o the screen, it could then be replaced by a quicktime style movie file.

Which is, essentially, what it is trying to do on a screen that covers Sring's influences as well as hosting a variety of clips about him or featuring him.

I have attached some images to this post for reference.

In the uppe rright corner, where the TV should be, is a black spot. With a large pink rectangle around it. In my experience, it should be loading an asset here (of a television). And the pink area is showing the masked area. Below it is a blacked out area that looks like a person seated, also surrounded by a large pink rectangle.

Vlicking the remote causes the TV mask to enlarge, before a video vlip plays where you can see the edges of the televison present in the movie clip, but the actual static art asset isn't loading.

However, clicking someone in the audience (which highlights them with a spotlight) and then clicking the missing image of a seated man kicks off a multimedia clip of Sting talk about that person's influence. The entire pink area is missing at this point, which suggests to me that the media clip is either so large it is covering it, or the static image of the background around the media clip is loading during this time.

The fact this behaviour occurs both in dosbox and 86box (with clean images) is what confuses me most.

If it was the emulation itself, I wouldn't expect it to be in both scenarios.
If it was a problem with the disk images, I wouldn't expect it to persist on a clean copy that is properly imaged.
I suppose it's possible the program was just released like this... but that seems incredibly unlikely to me.

My hope is someone here is Director knowledge, or maybe even knolwedge of this App, might have some thoughts on how to continue troubleshooting this.

I'd like to get it running on original hardware to verify the issue doesn't exist. I may try and get a 9x machine running this weekend to verify.

In the mean time, helpful input would be increibly welcome. Thanks.