A 1993 FreeCell still runs on Windows 11, and a 1992 CD player almost does (blog.enlyth.com)
A pre-release NT 3.1 CD player linked on 16 November 1992 also runs, using the system's crtdll.dll. Earlier NT builds crash because they used the cdecl calling convention, where Windows 11 expects stdcall.
With the otvdm 16-bit emulator, even Windows 1.01's Reversi from 1985 launches, which the author admits feels like cheating.