For a during I’ve been wondering concerning a silly question, which is, what’s the oldest use alongside a GUI that volition motionless run on Windows 11 without modifications or emulation.
Given Windows’ outstanding backwards compatibility, I expected the answer to be item impressively old.
Sadly, Windows 11 can’t run 16-bit Windows programs by itself, since 64-bit Windows has no NTVDM, so we’re going to have to discover item from the first NT era.
I recall asking this inquiry a during ago on an anonymous forum, anywhere person pointed me to Win32s, and suggested to discover an first publish type of it alongside FREECELL.exe.
So I did exactly that, and lo and behold, FREECELL.EXE alongside a date modified of 22-Feb-93 operating and completely playable, without any changes on the latest type of Windows 11:

At the period of this post, that’s a 33 years and 8 months old application, which is impressively nearly as old as me.
So I kinda idea “cool”, considered this a solved mystery and forgot concerning it shortly afterwards. But for several reason, this inquiry popped into my intellect again lately and this period I decided to dig deeper to see if I can discover item older.
Digging through old Windows versions on the Internet Archive, I established several first NT 3.1 pre-release versions that seemed promising, but the chief matter seemed to be either incompatibility alongside today’s executable format or API changes that came afterward in development.
The earliest 1991 versions used a outline PE format not compatible alongside contemporary Windows, and builds up to mid-1992 assumed the cdecl calling gathering alternatively of stdcall for Windows API calls, so arguments would get removed twice, as such:
push hwnd ; 4 bytes of args call [ShowWindow] ; Win11 ShowWindow is stdcall, ends alongside "ret 4" and removes them add esp, 4 ; the 1992 visitant removes them again
Which would understandably logic the program to crash.
There was one use that caught my eye though, from Build 347, and that was CDPLAYER.EXE, connected on 16-Nov-1992. By afterward the calling gathering was fixed, but the another programs in that build collision in their bundled C runtime. CDPLAYER.EXE avoids that by using the system’s crtdll.dll, and Windows 11 motionless ships a crtdll.dll in SysWOW64.
If you commencement the program, you get item akin this:

That is because, duh, my device doesn’t have a CD-ROM drive. But you can use a small DLL (cdemu.dll) to emulate one alongside several counterfeit audio data and really get it to perform audio:

Pretty chill for a program that’s nearly 34 years old!
So before I mentioned that 16-bit programs are out of the image since they are no longer supported.
But if you want, you can use item akin otvdm to run older Windows applications.
Behold, a completely playable type of REVERSI.EXE dated 15-Nov-1985 operating on Windows 11, taken from Windows 1.01:

And although using otvdm does awareness akin cheating, I idea it was chill adequate to contain in this post.