TheJoe: I'm running 64-bit Windows and I'm going to set myself a little challenge.
Wine is designed to run Windows programs on Linux. You can run 32-bit Windows apps on 64-bit Linux.
Wine is also cross-platform. I'm going to attempt to compile Wine on 64-bit Windows and see if it runs a 16-bit executable.
Wish me luck.
Wishbone: Good luck :-D
There was actually a Wine for Windows once, but they've stopped compiling it for the Windows platform now. Sadly, noone else seems to be doing so either. I've looked for it extensively, precisely as a way of running 16-bit Windows games on a 64-bit Windows. So if you happen to succeed, be sure to let us know.
I was not successful, but only because of a wrong configure flag. I actually just compiled Wine for a processor that doesn't exist; now that's an achievement.
I talked to a Wine dev and only the DLLs and Wine programs (WineD3D, Wine DXDiag, winecfg etc) can be actually be compiled for Windows. Wineserver which is the fake NT Kernel that Wine requires cannot be made for Windows simply because there's "too much Linux" in it.
That said, I don't believe that Wine on Windows would require Wineserver. I believe that only the DLLs would be required, but that raises the question "Just how do you use them?"
I'm going to look into using AndLinux, which is a minimal port of CoLinux; it's actually a miniature Linux Kernel that runs on Windows, effectively making Linux programs work on Windows. I'll attempt to build Winedows again if I can figure out the right flag for the configure script and then see if I can get an application to use Wine DLLs instead of Windows DLLs.